2,4-Dimethylphenol
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2,4-Dimethylphenol
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CAS No:
105-67-9
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Formula:
C8H10O
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Chemical Name:
2,4-Dimethylphenol
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Synonyms:
Phenol,2,4-dimethyl-;2,4-Xylenol;2,4-Dimethylphenol;4,6-Dimethylphenol;1-Hydroxy-2,4-dimethylbenzene;m-Xylenol;4-Hydroxy-1,3-dimethylbenzene;2,4-DMP;NSC 3829
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CAS No:
Description
YELLOW-TO-BROWN LIQUID OR COLOURLESS CRYSTALS.
2,4-dimethylphenol appears as colorless crystals or clear, dark amber liquid.|Liquid|YELLOW-TO-BROWN LIQUID OR COLOURLESS CRYSTALS.
2,4-dimethylphenol appears as colorless crystals or clear, dark amber liquid.|2,4-Dimethylphenol is a hydroxytoluene.
2,4-Dimethylphenol Basic Attributes
122.1644
122.16
203-321-6
5OD803C081
0458
3829
2261|3082
DTXSID2021864
Crystals|NEEDLES FROM WATER|Colorless needles
2907199090
Characteristics
20.23000
2.40
2,4-dimethylphenol appears as colorless crystals or clear, dark amber liquid.
0.9650 g/cm3 @ Temp: 20 °C
24.54 °C
211.5 °C @ Press: 766 Torr
85.6±7.2 °C
1.540
H2O: 0.5 g/100 mL (25 ºC)
Rooms used for storage only should be soundly constructed and fitted with secure locks. Floors should be kept clear, and the pesticides clearly identified. /Pesticides/
0.102 mm Hg @ 25 deg C
Explosive limits , vol% in air: 1.1-6.4
0.5 mg/l (taste threshold concn)
7.15e-11 cm3/molecule*sec
9.51e-07 atm-m3/mole|Henry's Law constant = 1.7X10-5 atm-cu m/mol @ 25 °C
pKa= 10.60 at 25 °C
Dipole moment: 1.48 debyes (benzene, 20 °C); 1.98 debyes (benzene, 60 °C)|Hydroxyl radical rate constant = 7.20X10-11 cu-cm/molc sec @ 25 °C
Insoluble in water.
Phenols and Cresols
2,4-DIMETHYLPHENOL is a very weak acid (pKa = 10.6) (NTP, 1992). Incompatible with acid chlorides, acid anhydrides, bases and oxidizing agents. Corrodes steel, brass, copper and copper alloys (NTP, 1992).
599 °C
64.96 kJ/mole @ 210.98 °C
Safety Information
II
6.1
UN 2261 6.1/PG 2
3
R24/25;R34;R51/53
S26-S36/37/39-S45-S61-S36/37-S16-S7
ZE5600000
T:Toxic;N:Dangerousfortheenvironment;
Separated from food and feedstuffs, acid anhydrides, acid chlorides, bases and oxidants.
Stable under normal temperatures and pressures.
P210-P260-P280-P301 + P310-P311
H225-H301 + H311 + H331-H370
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U101, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.|A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.|A pilot plant study was conducted to evaluate the fate and behavior of 22 toxic organic compounds in conventional activated sludge wastewater treatment plants. The organic cmpd, 2,4-dimethylphenol, spiked at a nominal concn of 50 ug/l was about 99% removable. Results showed that biodegradability was variable and was a function of molecular structure.|The effectiveness of anaerobic filters containing granular activated carbon in treating synthetically prepared wastewaters that contained phenols, polycyclic hydroxy compounds, monocyclic N-aromatics, polycyclic N-aromatics, & aliphatic acids was evaluated. The ability of the activated carbon to retain these compounds along with its external surface, which provides vast sheltered microbial attachment areas, renders activated carbon a very unique medium for anaerobic filter treatment of coal gasification wastewater.|For more Disposal Methods (Complete) data for 2,4-DIMETHYLPHENOL (6 total), please visit the HSDB record page.
USEPA; Ambient Water Quality Criteria Doc: 2,4 Dimethylphenol (1980) EPA 440/5-80-044.|Toxikologische Bewertung. 137 (1995). Summary and assessment of 2,4-xylenol.|EPA. EPA/600/8-88/031 p.30 (1987). Health effects assessment for dimethylphenols.|Tucker JD et al; Mutat Res 297 (2): 101-80 (1993). Sister-chromatid exchange: second report of the Gene-Tox Program.
This chemical is probably combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
|Danger|H301 (99%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P272, P273, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P333+P313, P361, P363, P391, P405, and P501|Aggregated GHS information provided by 501 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P264, P270, P273, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P361, P363, P391, P405, and P501|H312: Harmful in contact with skin [Warning Acute toxicity, dermal]|P260, P264, P270, P273, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P309+P311, P310, P312, P314, P321, P322, P363, P405, and P501|H303: May be harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P272, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P309+P311, P310, P312, P314, P321, P322, P333+P313, P363, P405, and P501
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)|Use water spray, powder, alcohol-resistant foam, carbon dioxide.
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this chemical under ambient temperatures, and protect it from moisture and oxidizing materials. If possible, it would be prudent to store this compound under inert atmosphere. (NTP, 1992)
MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|Some data suggesting breakthrough times /for butyl rubber/ of approximately an hour or more. /Aromatic hydroxyl cmpd/|Breakthrough times /for neoprene/ greater than one hour reported by (normally) two or more testers. /Aromatic hydroxyl cmpd/|Breakthrough times /for polyvinyl alcohol/ less (usually ... /markedly/ less) than one hour reported by (normally) two or more testers. /Aromatic hydroxyl cmpd/
Explosive limits , vol% in air: 1.1-6.4
FOUNDRY PLANT WASTE GASES WERE DEODORIZED WITH POTASSIUM PERMANGANATE, AND DEODORIZATION EFFICIENCY WAS MEASURED BY PRESENCE OF 2,4-XYLENOL IN SCRUBBED WASTE GASES.
Smoking, eating, and drinking before washing should be absolutely prohibited when any pesticide ... is being handled or used. /Pesticides/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Xylenols; Xylenols, liquid; Xylenols, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Xylenols; Xylenols, liquid; Xylenols, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Xylenols; Xylenols, liquid; Xylenols, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Xylenols; Xylenols, liquid; Xylenols, solid/|For more DOT Emergency Guidelines (Complete) data for 2,4-DIMETHYLPHENOL (8 total), please visit the HSDB record page.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. If liquid: collect leaking liquid in covered plastic containers.
Separated from food and feedstuffs, acid anhydrides, acid chlorides, bases and oxidants.
No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
The substance is corrosive to the skin, respiratory tract and eyes. Corrosive on ingestion. Inhalation of the aerosol may cause lung oedema.
Repeated or prolonged contact may cause skin sensitization.
NO open flames.
PREVENT DISPERSION OF DUST! PREVENT GENERATION OF MISTS! STRICT HYGIENE!
Use ventilation, local exhaust or breathing protection.
Protective clothing. Protective gloves.
Wear safety goggles, face shield or eye protection in combination with breathing protection.
U101; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate.
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
U101; As stipulated in 40 CFR 261.33, when 2,4-dimethylphenol, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).
2,4-Dimethylphenol was detected in raw sludge and treated sludge, concns unknown, in samples taken from 37 water pollution control plants in Ontario, Canada between January and July 1986(1). Waste water from the gasification of Indian Head lignite coal in North Dakota was determined to have an estimated 2,4/2,5-dimethylphenol concn of 368 mg/l(1). A summary of analysis for 2,4-dimethylphenol in effluent reports that it was found 3 times in residential, 8 times in industrial, and 2 times in commercial effluent, with an overall source average discharge concn of 0.7, 0.0, and 74.0 ug/l, respectively(3). 2,4-Dimethylphenol was identified but not quantified in leachate collected from a Swedish municipal landfill in May 1990(4). Groundwater and soil from 91 waste sites at 18 Department of Energy (DOE) facilities were analyzed; 2,4-dimethylphenol was found at one of the facilities in groundwater, concn not quantified(5).|2,4-Dimethylphenol was found in six effluents in an EPA survey (4000 samples) of effluents covering 46 industrial categories(1). Industries with positive levels of 2,4-dimethylphenol included iron and steel manufacturing, petroleum refining, organics and plastics, rubber processing, organic chemicals, and publicly owned treatment works(1). 2,4-Dimethylphenol was detected in 3.4% of 1321 effluent samples reported in STORET, EPA's water quality data base (1975-82)(2) and, in two out of five effluents of hazardous waste incinerators(3) and at 10 ug/l in urban runoff in Washington, DC(4). This constituted a 2% frequency of detection in the National Urban Runoff Program, which examined 86 runoff samples from 15 USA cities(4). The final effluent of Los Angeles County Municipal Wastewater Treatment Plant was found to contain 5 and <10 ppb 2,4-dimethylphenol in July 1978 and Nov 1980, respectively(5). Of 18 advanced water treatment effluents analyzed, 2,4-dimethylphenol was found in effluents at Lake Tahoe, CA (2 ng/l) and Blue Plains, WA (1 and 8.9 ng/l)(6).
0.3% of 310 samples from STORET (EPA water quality database) stations reported detectable amounts of 2,4-dimethylphenol in sediment in 1975-82(1). 2,4-Dimethylphenol was detected in a soil sample at the site of a former pine-tar manufacturer in Gainesville, FL(2) and in soil on 7 occasions at a closed wood-to-charcoal conversion plant in McKean county, PA, concn ranging from 1100-390,000 ug/kg(3). 2,4-Dimethylphenol was identified at an unauthorized disposal site in Pemberton Township, NJ in two samples of surface soil (avg concn= 220 ug/kg), but was not detected in subsurface soil(4).
URBAN/SUBURBAN: In 1984, a gas phase concn of 2,4-dimethylphenol (combined with 2,5-dimethylphenol) was detected in 7 of seven rain events in Portland, OR, at concns ranging from 15-70 ng/cu m, 33 ng/cu m; the amount associated with adsorption to particulate matter was <5% of the gas phase concn in every case and generally <1% of the gas phase(1). 2,4-Dimethylphenol was detected at 1 ug/cu m in the air outside an oil shale wastewater facility in Logan WA, but not in an undeveloped site in the oil shale region or in Boulder, CO(2). SOURCE DOMINATED: Although found in gasoline and diesel motor exhaust, 2,4-dimethylphenol was not detected in an Allegheny Mountain highway tunnel(3).
IDENTIFIED IN PARTICULATE PHASE OF TOBACCO SMOKE: 2,4- AND 2,5-DIMETHYLPHENOLS, 2000 UG/100 CIGARETTES. /FROM TABLE/|2,4-Dimethylphenol was identified as a component of cigarette smoke, with concns ranging from 0.7 to 2.1 mg/100 cigarettes (analyzed with 2,5-dimethylphenol)(1).
Toxicity
A SPONTANEOUSLY DEVELOPING VASOCONSTRICTION IN ISOLATED PERFUSED LUNG AND THE VASOCONSTRICTION CAUSED BY ARTERIALLY INJECTED ATP 50 UG WERE BOTH INHIBITED BY THE ADDITION TO THE PERFUSATE OF VARIOUS PHENOLS INCLUDING 2,4-XYLENOL.
LD50 Rat dermal 1040 mg/kg|LD50 MOUSE IP 150 MG/KG|LD50 Rat oral 2300 mg/kg|LD50 Mouse oral 809 mg/kg|For more Non-Human Toxicity Values (Complete) data for 2,4-DIMETHYLPHENOL (6 total), please visit the HSDB record page.
2,4-Dimethylphenol is a constituent of coal(1) and has been found in tobacco and marijuana mainstream smoke(2,3), and in black tea(4).
/SRP/: DIMETHYLPHENOLS OCCUR IN SHALE OIL PROCESS WATER, INDUSTRIAL WASTE WATER, AIRBORNE PARTICULATES, ... AND EVOLUTES FROM WASTE CHEMICAL DUMPS. /DIMETHYLPHENOLS/|The nature and extent of pollution was determined at the site of a former pine tar manufacturer in Gainsville, Florida. In 1979 the EPA conducted an investigation of this area. Compound distribution at various areas about the site revealed that, in addition to groundwater leaching of soluble phenolics, insoluble contaminants were spread by a dike-breach incident and subsequent construction activities. Differences in the patterns of chemicals in various wells suggested that more than one source of pollution occurred. The distribution of compounds about the site indicated that a general clean-up would not be cost-effective. Placement of an intereceptor to collect groundwater seepage that contaminated surface water was considered as an alternative. One of the 43 compounds identified in soil extracts was 2,4-dimethylphenol.|2,4-Dimethylphenol's use for the preparation of coal tar disinfectants (1), in the manufacture of artificial resins(1), as a constituent of coal tar creosote (0.5 wt%)(2), as a raw material for antioxidants for gasoline and rubber(3), and as a component of automobile and diesel exhaust(4,5) may result in its release to the environment through various waste streams(SRC). In addition, 2,4-dimethylphenol may also be released in asphalt and roadway runoff, washing of dyed materials, and general use of pharmaceuticals, fuels, plastic, and pesticides(2). Dimethylphenols, of which 2,4-dimethylphenol is an isomer, are components of disinfectants, solvents, insecticides, fungicides, plasticizers, rubber chemicals, additives to lubricants and gasolines, wetting agents and dyestuffs(9).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 430(SRC), determined from a log Kow of 2.30(2) and a regression-derived equation(3), indicates that 2,4-dimethylphenol is expected to have moderate mobility in soil(SRC). Volatilization of 2,4-dimethylphenol from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.7X10-5 atm-cu m/mole (4). 2,4-Dimethylphenol is not expected to volatilize from dry soil surfaces(3) based upon a vapor pressure of 0.102 mm Hg at 25 °C(5). 2,4-Dimethylphenol has been reported to completely biodegrade from soil in 4 days at a temperature of 19 °C(6) and the biodegradation half-life of 2,4-dimethylphenol from Texas soil and Mississippi soil was determined to be 1.5 and 3.5 days, respectively(7).|AQUATIC FATE: Based on a classification scheme(1), a Koc value of 430(SRC), determined from a log Kow of 2.30(2) and a regression-derived equation(3), indicates that 2,4-dimethylphenol is expected to adsorb very little to suspended solids and sediment in water(SRC). 2,4-Dimethylphenol is expected to volatilize from water surfaces(3,SRC) based upon a Henry's Law constant of 1.7X10-5 atm-cu m/mole(4). Estimated volatilization half-lives for a model river and model lake are 3 days and 22 days, respectively(3,SRC). According to a classification scheme(5), a BCF of 150 in bluegill sunfish(6) suggests bioconcentration in aquatic organisms is moderate(SRC). In humic waters, degradation by the reaction with peroxy radicals should ensue with a half-life on the order of hours(7). 2,4-Dimethylphenol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). Screening studies indicate that 95% removal of 2,4-dimethylphenol was obtained after 5 days using an activated sludge inoculum(8). In addition, it has been reported that 2,4-dimethylphenol was readily degraded in St. Lawrence River water(9). Methanogenic consortia failed to anaerobically biodegrade 2,4-dimethylphenol after 24 days in one study(10); in two standardized anaerobic bioassays using a digester sludge, 2,4-dimethylphenol yielded no more than 10% of theoretical methane(11).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4-dimethylphenol, which has a vapor pressure of 0.102 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,4-dimethylphenol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 5.3 hours(SRC) from its rate constant of 7.20X10-11 cu cm/molecule-sec at 25 °C(3). 2,4-Dimethylphenol has an absorption band at 296 nm (maximum) and extends over 320 nm, thus making it a candidate for direct photochemical degradation(5,6). Night-time degradation in urban areas should occur rapidly through reaction with atmospheric nitrate radicals, as rate constants for this reaction with phenolic compounds are approximately 250 times faster than with hydroxyl radicals(7,SRC).
The rate constant for the vapor-phase reaction of 2,4-dimethylphenol with photochemically-produced hydroxyl radicals has been determined to be 7.20X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 5.3 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). 2,4-Dimethylphenol has an absorption band at 296 nm (maxima) which extends over 320 nm, thus making it a candidate for direct photochemical degradation(2,3). Night-time degradation in urban areas should occur rapidly through reaction with atmospheric nitrate radicals, as rate constants for this reaction with phenolic compounds are approximately 250 times faster than with hydroxyl radicals(4,SRC). Peroxy radicals found in humic waters react with phenols; the half-lives can be measured in hours(5). 2,4-Dimethylphenol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3).
A BCF of 150 was determined for 2,4-dimethylphenol in bluegill sunfish and 28 days exposure(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is high.
The Koc of 2,4-dimethylphenol is estimated as 430(SRC), using a log Kow of 2.30(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,4-dimethylphenol is expected to have moderate mobility in soil(SRC). The estimated Koc for 2,4-dimethylphenol is consistent with the Koc in river sediment and coal sediment from a pond near Leipzig, Germany which was determined to be 120 and 105 (log Koc = 2.08 and 2.02), respectively(4).
The Henry's Law constant for 2,4-dimethylphenol is 1.7X10-5 atm-cu m/mole(1). This Henry's Law constant indicates that 2,4-dimethylphenol is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 3 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as approximately 22 days(SRC). 2,4-Dimethylphenol's Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces is expected to occur(SRC). 2,4-Dimethylphenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.102 mm Hg(3).
GROUNDWATER: The concn of 2,4-dimethylphenol in groundwater collected from a wood-preserving plant at Pensacola, FL in 1985 was determined to be 1.33-9.68 mg/l(1). Groundwater samples collected from three creosote- contaminated sites in Denmark, date unspecified, were found to contain 2,4-dimethylphenol ranging in concn from below detection to 2090 ug/l, analyzed with 2,5-dimethylphenol(2). 10 of 11 wells underlying a former pine-tar manufacturing facility in Gainesville, FL were found to contain 2,4-dimethylphenol ranging in concn from 1-9400 ug/l (including 2,5-dimethylphenol)(3). 2,4-Dimethylphenol was detected at a concn of 0.2 mg/l in groundwater near an abandoned wood preservative manufacturing plant in Florida(4). Water samples collected during December 1986 from Gas Works Park, Seattle, WA were found to contain 2,4-dimethylphenol ranging in concn from below detection to 1.0 mg/l(5). Studies near a wood preserving facility in Pensacola, FL detected 2,4-dimethylphenol in ground water at all four sites in a sand aquifer, concns ranging from 0-5.65 mg/l; while detected in samples from 6,12, 18, and 24 m depth, 2,4-dimethylphenol was not detected at 30 m depth(6). 2,4-Dimethylphenol was also identified in the leachate from a sanitary landfill in Barcelona, Spain(7).|GROUNDWATER: Samples collected on September 9, 1980 from an uncontaminated well bordering a US Army installation site in Bristol, RI revealed that the average concn of 2,4-dimethylphenol was 26 ug/l(1). A study of groundwater contamination at 6 Superfund sites across the U.S. detected 2,4-dimethylphenol in the Biscayne, FL Aquifer study area, concn of 110 ug/l(2). The average concn of 2,4-dimethylphenol in the groundwater near 5 wood treatment facilities sampled in the US was 1,219 ug/l(3). The concn of 2,4-dimethylphenol identified at a closed wood-to-charcoal conversion plant in McKean county, PA in 2 of 3 groundwater wells was estimated as 34 and 360 mg/l(4). At a closed, filled, landfill at Hipps Road landfill, FL, 2,4-dimethylphenol was detected in 1 of 3 groundwater wells at 13 ug/l(5). 2,4-Dimethylphenol was identified in groundwater at a unauthorized disposal site in Pemberton Township, NJ at a concn of 32 ug/l(6).|DRINKING WATER: 2,4-Dimethylphenol was listed as having been identified in drinking water in the USA(1,2) as well as being detected 5 times in finished drinking water samples collected across the United States in 1977(3).|SURFACE WATER: 2,4-Dimethylphenol has been detected in 1% of 804 samples reported in STORET, EPA's water quality database for 1975-82(1), immediately downstream from waste input into a creek from a former pine-tar manufacturing facility in Gainesville, FL, concn ranging from 10-200 ug/l(2), and in Smith Creek in Sept 1980, near, and shortly after the Mt. St. Helens, WA explosion, but not found in 3 nearby lakes(3). 2,4-Dimethylphenol has also been identified in on-site lagoons at a covered wastefill in Forest Waste, MI, at a concns estimated at 40 and 100 ug/l(4) and in an aqueous sample collected near Quantico, VA, concn <2 ug/l(5).|RAIN/SNOW: The concentration of 2,4- and 2,5-dimethylphenol, combined in rainwater for seven events in Portland, OR ranged from 300 to 1300 ng/l, 820 ng/l avg(1).
Cigarette and marijuana smoking groups and those exposed to cigarette smoke inhale ug quantities of 2,4-dimethylphenol. The NIOSH has estimated that 11,000 people in the USA are occupationally exposed to cresol containing 2,4-dimethylphenol.|NIOSH (NOES Survey 1981-1983) has statistically estimated that 7,786 workers are potentially exposed to dimethylphenol in the US, isomer not specified(1). Occupational exposure to 2,4-dimethylphenol may occur through inhalation of this compound at workplaces where 2,4-dimethylphenol is produced or used(SRC). The general population may be exposed to 2,4-dimethylphenol via inhalation of ambient air (i.e., tobacco smoke(2) and automobile exhaust(3)), ingestion of food(4), and contact with other products that may contain 2,4-dimethylphenol(5).
Urine from 35 varnishing workers in six different workplaces contained an average 2,4-dimethylphenol concn of 3.8 mg/l; phenols are metabolites of benzene and alkyl benzenes in the varnish(1).
Drug Information
SUBJECTS WERE EXPOSED TO M-XYLENE AT CONCN OF ABOUT 3.9 MMOL/CU M FOR 5 DAYS, 6 HR/DAY. RATE OF 2,4-XYLENOL EXCRETION SHORTLY AFTER EXPOSURE WAS ABOUT 1-2% OF THAT FOR METHYLHIPPURIC ACID EXCRETION AND PULMONARY EXCRETION OF UNCHANGED XYLENE WAS ABOUT 4% OF UPTAKE.|The concn of 2,4-dimethylphenol was determined /in/ several tissues of the rat after 6 hr constant iv infusion and after iv bolus injection. 2,4-dimethylphenol was distributed rapidly in the brain and liver, /and had/ high tissue-plasma concn ratios for the brain, liver, and fat. Accumulation of 2,4-dimethylphenol in these tissues was negligible.|FOLLOWING IV ADMIN OF 17 MG/KG OF THE 2,4-ISOMER TO RATS, THE BRAIN ACCUMULATED THE HIGHEST AMT ON A PER G BASIS, FOLLOWED BY FAT AND LIVER. RATIOS OF BRAIN, LIVER AND FAT TO PLASMA /CONCN/ WERE APPROX 1, 1.5 AND 2, RESPECTIVELY.|2,4-DIMETHYLPHENOL DISTRIBUTED RAPIDLY THROUGH THE BODY AFTER IV BOLUS ADMIN OF 30 MG/KG. PLASMA, LIVER AND FAT CONCN DISAPPEARED PRIOR TO 60 MIN BUT PERSISTED IN THE BRAIN.|Associations between o-cresol, p-cresol, m-cresol, 2,4-xylenol, 2,5-xylenol, 3,4-xylenol, and 3,5-xylenol exposure levels and urinary phenol excretion were examined in the coke facility industry. The subjects consisted of 76 exposed workers employed in the tar distillation process and 34 controls. ... Urinary metabolite levels were corrected for specific gravity and creatinine. The time weighted average exposure concentrations in the breathing zones of the tar distillation workers were ... 0.02 to 0.04 mg/cu m for xylenols. ... The urinary xylenol levels of exposed workers ranged from 0.12 to 0.97 mg/l with specific gravity correction. In control urine samples, the specific gravity corrected xylenol concentrations ranged from 25 x 10(-3) to 43 x 10(-3) mg/l. Significant correlations were observed between the ambient levels and urinary concentrations of phenol, o-cresol, and the xylenols, with coefficients ranging from 0.45 to 0.82. The author concludes that the biological monitoring of urinary xylenols may be used as a means of measuring xylenol exposure in coke facility workers.
METABOLISM OF 2,4-DIMETHYLPHENOL IN ANIMALS IS VERY SIMILAR TO THAT OF CRESOLS ... .|Rats were admin 2,4-dimethylphenol for 6 hr constantly by iv infusion or iv bolus injection. 2,4-Dimethylphenol was rapidly metabolized to its conjugates (94.3%) within 30 min; the glucuronide constituted 53% and other conjugates 41% /in plasma/.|IN WORKERS SIMULTANEOUSLY EXPOSED TO ETHYLBENZENES AND XYLENES, 2,4-DIMETHYLPHENOL, A METABOLITE OF M-XYLENE, COULD NOT BE DETECTED.|HYDROXYLATION OF AROMATIC HYDROCARBONS WAS STUDIED FOLLOWING THEIR ORAL ADMINISTRATION TO RATS THAT ALSO RECEIVED A PURIFIED DIET CONTAINING NEOMYCIN TO REDUCE THE LEVELS OF NORMALLY OCCURRING SIMPLE URINARY PHENOLS. PHENOLIC METABOLITES WERE QUANTITATIVELY ESTIMATED IN HYDROLYZED URINE SAMPLES BY GAS CHROMATOGRAPHY. M-XYLENE ADMINISTERED AT A DOSE OF 100 MG/KG WAS METABOLIZED TO 2,4-DIMETHYLPHENOL TO THE EXTENT OF 0.9% OF THE DOSE GIVEN.|For more Metabolism/Metabolites (Complete) data for 2,4-DIMETHYLPHENOL (6 total), please visit the HSDB record page.|2,4-Dimethylphenol is a known human metabolite of m-xylene.
SYMPTOMS: Symptoms of exposure to this compound may include severe irritation of the skin and eyes, dizziness, stomach pain, exhaustion and damage to the liver and kidneys. Other symptoms include headache, nausea and vomiting. It may cause severe burns of the eyes and skin, irritation of the respiratory tract and coma. It may also cause corrosion of tissue of the mucous membranes and upper respiratory tract, eyes and skin. Inhalation may result in burning sensation, coughing, wheezing, laryngitis and short ness of breath. Inhalation may be fatal as a result of spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis and pulmonary edema. Symptoms of exposure to this class of compounds include profuse sweating, skin sensitization, painless blanching or erythema of the skin, intense thirst diarrhea, cyanosis from methemoglobinemia, hyperactivity, stupor, fall in blood pressure, hyperpnea, abdominal pain, hemolysis and convulsions. If death from respiratory failure is not immediate, jaundice and oliguria or anuria may occur. ACUTE/CHRONIC HAZARDS: This compound is highly toxic by ingestion, inhalation or skin absorption. It is a severe irritant of the skin and eyes. It is corrosive to the skin, eyes, mucous membranes and upper respiratory tract. When heated to decomposition it emits acrid smoke, irritating fumes and toxic fumes of carbon monoxide and carbon dioxide. (NTP, 1992)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Phenols are very toxic poisons AND corrosive and irritating, so that inducing vomiting may make medical problems worse. IMMEDIATELY call a hospital or poison control center and locate activated charcoal, egg whites, or milk in case the medical advisor recommends administering one of them. If advice from a physician is not readily available and the victim is conscious and not convulsing, give the victim a glass of activated charcoal slurry in water or, if this is not available, a glass of milk, or beaten egg whites and IMMEDIATELY transport victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, assure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Administer activated charcoal ... . Dilution may be contraindicated because it may increase absorption. Do not use emetics ... . Cover skin burns with dry sterile dressings after decontamination ... . /Phenols and Related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W TKO /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors for hypotension with a normal fluid volume. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Phenols and Related Compounds/
The trichlorophenols and 2,4-dimethylphenol may be carcinogens.|2,4-Dimethylphenol appears to be a topical cocarcinogen, but its role as a primary cancer-producing agent is uncertain.|Lysol poisoning has been associated with incomplete abortions, shock, tachycardia, leukocytosis, hemolysis, fever, central nervous system irritability, respiratory ... /insufficiency/ associated with pulmonary edema and/or oil emboli, local tissue necrosis with uterine hemorrhage, and anemia.|The low-molecular-weight phenols 2-methylol phenol, 4-methylol phenol, 2,4,6-trimethylol phenol, 3-methylol phenol, 2,4-dimethylol phenol, and 2,6-dimethylol phenol are contact sensitizers in resins based on phenol and formaldehyde. ... In patients hypersensitive to resins based on phenol and formaldehyde and methylphenol, it is for diagnostic, therapeutic and preventive reasons necessary to know their cross-reaction patterns, which this study was therefore designed to investigate. In patients with contact allergy to a resin based on phenol and formaldehyde and at least 1 methylphenol, additional patch testing was performed with 6 methylphenol and 13 chemically related compounds. The 19 substances were tested at equimolar concentrations and in serial dilutions. Investigations by high-performance liquid chromatography were carried out to exclude contamination as the cause of the patch test reactions. Probable cross-reacting substances were o-cresol, p-cresol, salicylaldehyde, 2,4-dimethylphenol, and 2,6-dimethylphenol.|Moderately toxic by ingestion and skin contact.
2,4-dimethylphenol
The substance can be absorbed into the body by inhalation, by ingestion and through the skin.
Burning sensation. Cough. Sore throat. Shortness of breath.
Redness. Pain. Skin burns.
Redness. Pain. Severe burns.
2,4-Dimethylphenol Use and Manufacturing
Coal tar fractionation; processing.|The insertion of methyl groups into phenol to produce ... xylenols is a commercial process of considerable utility. The process commonly employed is methylation with methyl alcohol over a solid catalyst, generally a modified metal oxide, at temp in the range of 300-450 °C. /Xylenols/|Fractionation of mixed xylenols
Intermediates
Cleaning and furnishing care products
10,000,000 - 50,000,000 lb|(1977) AT LEAST 9.99X10+8 G
2,4-XYLENOL AND M-CRESOL IN AN EMULSIFIED FORMULATION OF HYDROCARBONS AND WATER. HORTICULTURAL FORMULATION FOR ERADICATION OF CROWN GALL TUMORS. /BACTICIN/|Xylenol 100; a high purity fraction of 2,4- and 2,5- xylenol (ortho xylenols); typical composition: 2,4- 2,5-xylenol 93%; meta para cresol 2%; other xylenols 5% /From table/|Pitt-Consol Xylenol 410 is a synthetic xylenol blend ... homolog distribution, wt %: 2,6-xylenol, 1; 2,4-xylenol, 42; 2,5-xylenol, 43; 2,3-xylenol group, 14. /Xylenol 410/|Bulk Lysol Brand Disinfectant, soluble concentrate, 1.5% 2,4-xylenol.|For more Formulations/Preparations (Complete) data for 2,4-DIMETHYLPHENOL (11 total), please visit the HSDB record page.
All other basic organic chemical manufacturing|Phenol, 2,4-dimethyl-: ACTIVE|ISOMERIZATION OF 1,4-DIMETHYLBENZENE OXIDE TO 2,4-DIMETHYLPHENOL WAS ANALOGOUS TO METHYL MIGRATION IN ENZYMIC CONVERSION OF 4-METHYLPHENYLALANINE TO 3-METHYLTYROSINE WITH PHENYLALANINE HYDROXYLASE.|Discontinued by TUCO, Division of the Upjohn Co. /Bacticin/
SEPARATION OF 13 ISOMERIC ALKYLPHENOLS WAS STUDIED BY HIGH PERFORMANCE LIQUID (HPLC), GAS LIQUID (GLC), & HIGH PERFORMANCE THIN LAYER CHROMATOGRAPHY (HPTLC) TECHNIQUES. /ALKYLPHENOLS/|A SEPARATION TECHNIQUE WAS DEVELOPED USING REVERSE PHASE HIGH PRESSURE LIQ CHROMATOGRAPHY TO ISOLATE CHEMICALS HAVING POTENTIALLY HIGH LIPID WATER PARTITION COEFFICIENTS. RETENTION VOLUME DATA FOR SELECTED CHEMICALS USING THIS METHOD FOR ANALYSIS IS PRESENTED. DATA ARE GIVEN FOR 2,4-DIMETHYLPHENOL.|High performance liquid chromatography separation by isocratic elution of a wide range of substituted phenols, including the priority pollutant, 2,4-dimethylphenol, was investigated.|A gas liquid chromatography procedure is described for identification of 32 substituted phenols. This method involves a simple and reproducible derivatization step which forms stable phenol pentafluorobenzyl ethers for which the electron capture detector is highly sensitive. Gas liquid chromatogrphy retention time data of the derivatives on 6 packed and fused silica capillary columns are reported. The detection limits using fused silica capillary columns of all chloro-, alkyl- and mononitro-phenols studied are between 0.5 and 5 picograms. /Substituted phenols/|For more Analytic Laboratory Methods (Complete) data for 2,4-DIMETHYLPHENOL (23 total), please visit the HSDB record page.
A sensitive and reliable procedure is described for the detection of 10 most important phenolic metabolites of benzene, toluene, xylenes and ethylbenzene. The urine was acidified with sulfuric acid and steam distilled was performed on a fused silica capillary (SE 54; 30 m) with FID. 3-Ethylphenol was used as internal standard. For phenol; o-cresol and p-cresol; DL-1- and 2-phenylethanol; 3-methylbenzylalc, 2-ethylphenol; 2,4-, 2,3-, 3,4-dimethylphenol, within series relative derivation was 2.3-16.8%. The recovery rates were 89-109%. The detection limit was 0.3 mg/l. Linearity was tested .ltoreq.50 mg/l.|Four methods were developed for determining minor metabolites of ethylbenzene and xylene in the urine. Methods were developed for determining 1-phenylethanol, omega-hydroxyacetophenone, 4-ethylphenol, 2,4-dimethylphenol, and 3-methylbenzyl alcohol. Following pretreatment of the sample, metabolites were determined using gas liquid chromatography and a flame ionization detector. Either acid or enzymatic hydrolysis was used as treatment and the hydrolysates were extracted with dichloromethane or diethylether.|/Gas chromatographic determination of urinary phenol conjugates after acid hydrolysis/extractive acetylation./ A simple gas chromatographic procedure for determining phenols in urine was developed. ... Using 10 mg/l spikes of phenol, 2-methylphenol, 3-methylphenol, 4-methylphenol, 2,6-dimethylphenol, 2,5-dimethylphenol, 2,4-dimethylphenol, 3,5-dimethylphenol, 2,3-dimethylphenol, and 3,4-dimethylphenol yielded recoveries of 94.6 to 98.2%. ...
Food additives -> Flavoring Agents
Flavoring Agents
Computed Properties
Molecular Weight:122.16
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:122.073164938
Monoisotopic Mass:122.073164938
Topological Polar Surface Area:20.2
Heavy Atom Count:9
Complexity:90.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Recommended Suppliers of 2,4-Dimethylphenol
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