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Home > Encyclopedia > 3,5-Dimethylphenol

3,5-Dimethylphenol

3,5-Dimethylphenol structure

3,5-Dimethylphenol 

structure
  • CAS No:

    108-68-9

  • Formula:

    C8H10O

  • Chemical Name:

    3,5-Dimethylphenol

  • Synonyms:

    Phenol,3,5-dimethyl-;3,5-Xylenol;3,5-Dimethylphenol;1-Hydroxy-3,5-dimethylbenzene;1,3,5-Xylenol;NSC 9268;50356-23-5

  • Categories:

    Agrochemicals  >  Pesticide Intermediates

Description

WHITE-TO-YELLOW CRYSTALS WITH CHARACTERISTIC ODOUR.


3,5-dimethylphenol is a colorless to off-white crystalline solid. Odor threshold 1 ppm. Taste threshold 0.001 mg/L. (NTP, 1992)|DryPowder; Liquid|WHITE-TO-YELLOW CRYSTALS WITH CHARACTERISTIC ODOUR.


3,5-dimethylphenol is a colorless to off-white crystalline solid. Odor threshold 1 ppm. Taste threshold 0.001 mg/L. (NTP, 1992)|3,5-xylenol is a member of the class of phenols that phenol substituted by methyl groups at positions 3 and 5. It has a role as a xenobiotic metabolite. It derives from a hydride of a m-xylene.

3,5-Dimethylphenol Basic Attributes

122.16

122.16

774117

203-606-5

ONA760G0WA

1356

9268

2261

DTXSID1025148

Needles from water|Needles from petroleum ether|White crystals

29071400

Characteristics

20.2

2.35

White to orange Crystalline Solid

0.9680 g/cm3 @ Temp: 20 °C

64 °C

219.5 °C

109 °C

1.5362 (20ºC)

H2O: 5.3 g/L (25 ºC)

room temp

Vapour pressure, Pa at 25°C: 5

Relative vapour density (air = 1): 4.2

Oral-rat LD50: 608 mg/kg; Oral-Mouse LD50: 477 mg/kg

Flammable; burning releases toxic chloride fumes

vol% in air: 1.4

1.13e-10 cm3/molecule*sec

6.14e-07 atm-m3/mole

pKa= 10.19 at 25 °C

Sublimes above 219 °C|Heat of fusion: 18.00 kJ/mole @ 63.6 °C|Dipole moment: 1.76 debye (benzene, 20 °C)|Nitrobenzene/water partition coefficient 1.90 (log)|For more Other Experimental Properties (Complete) data for 3,5-DIMETHYLPHENOL (7 total), please visit the HSDB record page.

This chemical is hygroscopic. Insoluble in water.

Phenols and Cresols

3,5-DIMETHYLPHENOL is incompatible with bases, acid chlorides, acid anhydrides, and oxidizing agents. It corrodes steel, brass, copper, and copper alloys. (NTP, 1992)

Dust explosion possible if in powder or granular form, mixed with air.

13,767.7 g cal/g mole

Safety Information

II

6.1

UN 2261 6.1/PG 2

2

24/25-34

26-28-36/37/39-45-28A

ZE6475000

T

The warehouse is ventilated, low-temperature and dry; stored and transported separately from food raw materials, alkalis and oxidants

Stable under normal temperatures and pressures.

P260, P264, P270, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P361, P363, P405, P501

H301

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|Chemical Treatability of 3,5-Dimethylphenol; Concentration Process: Biological treatment; Chemical Classification: Phenols; Scale of Study: Unknown; Type of Wastewater Used: Pure compound (one solute in a solvent); Results of Study: 89.3% reduction based on chemical oxygen demand; rate of biodegradation 11.1 mg chemical oxygen demand/g hr (activated sludge process).|Chemical Treatability of 3,5-Dimethylphenol; Concentration Process: Activated carbon; Chemical Classification: Phenols; Scale of Study: Batch flow, Laboratory Scale; Type of Wastewater Used: Pure compound (one solute in a solvent); Results of Study: 100% reduction; 5% desorbed from carbon by elutriation with solvent. (Calgon FS-300 used. Solvents included pentane-acetone, diethylether, methylene chloride-acetone, chloroform-acetone, and acetone.)

Toxikologische Bewertung 139: 21 (1995). Summary and assessment of 3,5-xylenol.|Environmental Protection Agency EPA/600/8-88/031 p.30 (1987). Health effects assessment for dimethylphenols.

Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)|Combustible. Finely dispersed particles form explosive mixtures in air.

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P264, P270, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P361, P363, P405, and P501|H301 (99.74%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 2337 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, and P501|P201, P202, P260, P264, P270, P273, P280, P281, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P321, P330, 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: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, 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. (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 significantly less) than one hour reported by (normally) two or more testers. /Aromatic hydroxyl cmpd/

Explosive limits , vol% in air: 1.4-?

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

/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 3,5-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.

A severe eye irritant.

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers.

Separated from 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 eyes and skin. The substance is irritating to the respiratory tract. Corrosive on ingestion.

NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

PREVENT DISPERSION OF DUST!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles, face shield or eye protection in combination with breathing protection.

Waste water from the gasification of Indian Head lignite coal in North Dakota was determined to have an estimated 3,5-dimethylphenol concn of 968 mg/l, (mixture with 3- and 4-ethylphenol)(1). 3,5-Dimethylphenol was identified but not quantified in leachate collected from a Swedish municipal landfill in May 1990(2).

3,5-Dimethylphenol was qualitatively detected in soil samples at the site of a former pine-tar manufacturer in Gainsville, FL(1).

URBAN/SUBURBAN: In 1984, a gas phase concn of 3,5-dimethylphenol was detected in 7 of seven rain events in Portland, OR, at concns ranging from 9.7-42 ng/cu m, averaging 20 ng/cu m; the amount associated with adsorption to particulate matter was <5% of the gas phase concn in every case(1). 3,5-Dimethylphenol was detected at 1 ug/cu m in air outside an oil shale wastewater facility in Logan, WA, but not at a nearby undeveloped site in the oil shale region, or in urban Boulder, CO (detection limit = 0.05 ug/cu m)(2). SOURCE DOMINATED: Although found in gasoline and diesel motor exhaust, it was not detected in an Allegheny Mountain highway tunnel(3).

/SRP/: CONSTITUENT OF TOBACCO SMOKE.

Toxicity

highly toxic

LD50 Rat oral 608 mg/kg|LD50 Mouse oral 477 mg/kg|LD50 Mouse ip 156 mg/kg|LD50 Rabbit oral 1313 mg/kg

CONSTITUENT OF ... AUTOMOBILE EXHAUST.|Dimethylphenols, of which 3,5-dimethylphenol is an isomer, are present in the essential oils of various conifers, in tea, and in tobacco and tobacco smoke(1).

/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 3,5-dimethylphenol.|3,5-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 (0.7 wt%)(2), as the starting material for the pesticide 3,5-dimethyl-4-methylthiophenyl methylcarbamate(3), as a component of automobile and diesel exhaust(4-7) and as a by-product of the brewing industry(7) may result in its release to the environment through various waste streams(SRC). Dimethylphenols, of which 3,5-dimethylphenol is an isomer, are components of disinfectants, solvents, pharmaceuticals, insecticides, fungicides, plasticizers, rubber chemicals, additives to lubricants and gasolines, wetting agents and dyestuffs(8).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 190-1400(2), indicate that 3,5-dimethylphenol is expected to have low to moderate mobility in soil(SRC). Volatilization of 3,5-dimethylphenol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-6 atm-cu m/mole(SRC), determined from its vapor pressure of 0.041 mm Hg(4) and water solubility of 4880 mg/l(5). 3,5-Dimethylphenol is not expected to volatilize from dry soil surfaces based upon a its vapor pressure(3). 3,5-Dimethylphenol has been reported to degrade from soil in 11 days at a temperature of 19 °C(6).|AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 190-1400(2), indicate that 3,5-dimethylphenol is expected to adsorb in varying amounts to suspended solids and sediment in water(SRC). 3,5-Dimethylphenol may volatilize from water surfaces(3,SRC) based upon an estimated Henry's Law constant of 1.3X10-6 atm-cu m/mole(SRC), determined from its vapor pressure of 0.041 mm Hg(4) and water solubility of 4880 mg/l(5). Estimated volatilization half-lives for a model river and model lake are 30 days and 225 days, respectively(3,SRC). However, this model underestimates the volatilization half-life of 3,5-dimethylphenol since it does not take into account the effects of adsorption. The Koc of 1,400(2) suggests that volatilization could be attenuated by adsorption to suspended solids and sediments in water(SRC). This is apparent from the results of two EXAMS model runs, one in which the effect of adsorption was considered (half-life = 1,900 days in model pond) and one in which adsorption was ignored (half-life = 330 days in model pond)(6). According to a classification scheme(7), an estimated BCF of 36(3,SRC), from 3,5-dimethylphenol's log Kow(8), 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(9). 3,5-Dimethylphenol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). Biodegradation screening studies indicate that a 31% loss of theoretical oxygen demand occurred after 5 days(10,11). In addition, it has been reported that 3,5-dimethylphenol was readily degraded in St. Lawrence River water(12). Biodegradation under anaerobic conditions failed to occur after 24 days in one study using a river sediment inoculum(13), yet 45% degradation occurred after 8 weeks in another study using a contaminated groundwater digester(14).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3,5-dimethylphenol, which has a vapor pressure of 0.041 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3,5-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 3.4 hours(SRC) from its rate constant of 1.13X10-10 cu cm/molecule-sec at 25 °C(3). Atmospheric 3,5-dimethylphenol is known to be removed by rainwater(4). 3,5-Dimethylphenol has an absorption band at 281 nm (cyclohexane), and a shoulder may extend over 290 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 3,5-dimethylphenol with photochemically-produced hydroxyl radicals has been determined to be 1.13X10-10 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 3.4 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). 3,5-Dimethylphenol has an absorption band at 281 nm (cyclohexane), and a shoulder may extend over 290 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). 3,5-Dimethylphenol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3).

An estimated BCF of 36 was calculated for 3,5-dimethylphenol(SRC), using a log Kow of 2.35(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate.

676.08 L/kg|The Koc of 3,5-dimethylphenol in soils with an organic carbon content <0.15% ranged from 460-1400; the Koc for 3,5-dimethylphenol in Dormont soil (organic carbon content = 1.5%) was determined to be 190(1). According to a classification scheme(2), these Koc values suggest that 3,5-dimethylphenol is expected to have moderate to low mobility in soil(SRC).

The Henry's Law constant for 3,5-dimethylphenol is estimated as 1.3X10-6 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 0.041 mm Hg(1), and water solubility, 4880 mg/l(2). This Henry's Law constant indicates that 3,5-dimethylphenol is expected to volatilize from water surfaces(3). 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 approximately 30 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)(3) is estimated as 225 days(SRC). However, the volatilization half-life does not take into account the effects of adsorption. A Koc of 1,400(4) suggests that volatilization could be attenuated by adsorption to suspended solids and sediments in water(SRC). This is apparent from the results of two EXAMS model runs(SRC), one in which the effect of adsorption was considered, yielding an estimated half-life of 1,900 days in a model pond 2 m deep, and one in which the effect of adsorption was ignored, yielding an estimated half-life of 330 days in a model pond 2 m deep(5). 3,5-Dimethylphenol's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces is expected to occur(SRC). 3,5-Dimethylphenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.041 mm Hg(1).

GROUNDWATER: Studies near a closed wood preserving facility in Pensacola, FL detected 3,5-dimethylphenol in ground water ranging from 9.52 mg/l at 6 m depth and 0.01 mg/l at 24 m depth approximately 170 m from the plant site; at approximately 330 m from the site, 1.64 mg/l 3,5-dimethylphenol was detected at a depth of 6 m and 0.01 mg/l was detected at a depth of 24 m(1). The concn of 3,5-dimethylphenol in groundwater collected from a coal tar distillation/wood-treatment plant at St. Louis Park, MN in 1978 and from a wood-preserving plant at Pensacola, FL in 1985 was determined to be 6.21 mg/l and 1.24-16.8 mg/l, respectively(2). Groundwater samples collected from three creosote-contaminated sites in Denmark, date unspecified, were found to contain 3,5-dimethylphenol ranging in concn from below detection to 500 ug/l(3). 3,5-Dimethylphenol was detected at a concn of 1.3 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 3,5-dimethylphenol ranging in concn from below detection to 2.5 mg/l(5).|SURFACE WATER: 3,5-Dimethylphenol was qualitatively identified in samples from the St. Lawrence River near Montreal, Canada(1).|RAIN/SNOW: In 1984, 3,5-dimethylphenol was detected in seven rain events in Portland, OR, with concns ranging from 160-680 ng/l and averaging 490 ng/l(1).

3,5-Dimethylphenol was identified as a volatile component of floured chickpea (Cicer arietinum L.) seed(1), pork(2), bacon(3) and the Japanese dried food, Bonito(4).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 93 (56 of these are female) workers are potentially exposed to 3,5-dimethylphenol in the US(1). Occupational exposure to 3,5-dimethylphenol may occur through inhalation of this compound at workplaces where 3,5-dimethylphenol is produced or used(SRC). The general population may be exposed to 3,5-dimethylphenol via inhalation of ambient air (i.e., automobile exhaust(3)), ingestion of food(3,4), and contact with other products containing 3,5-dimethylphenol(6).

Drug Information

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.

3,5-DIMETHYLPHENOL (SYM-M-XYLENOL) YIELDS 3,5-DIMETHYLCATECHOL IN RABBITS. /FROM TABLE/|3,5-DIMETHYLPHENOL (SYM-M-XYLENOL) YIELDS 3,5-DIMETHYL PHENYL-BETA-DELTA-GLUCURONIDE, 3,5-DIMETHYLPHENYL SULFATE, & 2,6-DIMETHYLQUINOL IN RABBIT. /FROM TABLE/|3,5-DIMETHYLPHENOL (SYM-M-XYLENOL) YIELDS 3-HYDROXY-5-METHYLBENZOIC ACID IN PSEUDOMONAS. /FROM TABLE/

SYMPTOMS: Symptoms of exposure to this compound may include corrosion of the mucous membranes, upper respiratory tract, skin, and eyes; burning sensation, coughing, wheezing, laryngitis, and shortness of breath. Other symptoms may include severe irritation or burning of the eyes and skin; irritation of the respiratory system; dizziness, stomach pain, exhaustion, and coma. It can cause headaches, nausea, and vomiting. It can also cause dermatitis, muscular weakness, dimness of vision, irregular and rapid breathing, ringing in the ears, weak pulse, dyspnea, and unconsciousness. It can damage the kidneys, liver, pancreas, and spleen; and cause edema of the lungs. Inhalation may be fatal as a result of spasm, inflammation, and edema of the larynx and bronchi; chemical pneumonitis; and pulmonary edema. Chronic exposure can lead to digestive disturbances, nervous disorders, and skin eruptions. ACUTE/CHRONIC HAZARDS: This compound is highly toxic by inhalation, ingestion or skin absorption. It is corrosive and extremely destructive to tissue of the mucous membranes, upper respiratory tract, eyes and skin. When heated to decomposition it emits acrid smoke 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.


Wear protective gloves when administering first aid. Rinse and then wash skin with water and soap. 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/

TOXIC BY INGESTION AND SKIN ABSORPTION. /COMMERCIAL MIXTURES/

3,5-dimethylphenol

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

Cough. Dizziness. Headache.


MAY BE ABSORBED! Burning sensation. Skin burns.


Redness. Pain. Severe deep burns.

3,5-Dimethylphenol Use and Manufacturing

Methods of Manufacturing

The mixed xylenol is rectified to collect the 218-222°C distillate, which is cooled and crystallized and centrifuged to obtain industrial-grade 3, 5-xylenol. Recrystallize with toluene to obtain a finished product with a purity of 98%. Sulfonate m-xylene with concentrated sulfuric acid at 185°C, neutralize at 60-90°C, fusion at about 350°C, acidify with sulfuric acid, and finally perform vacuum distillation to obtain 3, 5-xylenol with a yield of 65 %.

Uses

Used in the production of pesticides, rubber accelerators, anti-aging agents, medicines, perfumes, phenolic resins, etc. It is also used as a cold rolling oil additive for steel rolling, which can extend the service life of cold rolling oil.


Photosensitive chemicals


Cleaning and furnishing care products

Production

1,000,000 - 10,000,000 lb|(1977) AT LEAST 4.99X10+8 G|(1981) PROBABLY GREATER THAN 2.27X10+6 G

50% in cresylic acid; solid grades|Xylenol 200; a concentrated fraction of 3,5-xylenol (meta xylenol); typical composition: 3,5-xylenol 50%; 2,4- and 2,5-xylenols 5%; 2,3- and 3,4-xylenol 12%; para-ethyl phenol 25%; C9 + phenol 8% /From table/

All other chemical product and preparation manufacturing|Phenol, 3,5-dimethyl-: ACTIVE

3,5-DIMETHYLPHENOL WAS AMONG 13 ISOMERIC ALKYLPHENOLS STUDIED BY HIGH-PERFORMANCE LIQUID, GAS-LIQUID AND HIGH-PERFORMANCE THIN-LAYER CHROMATOGRAPHIC TECHNIQUES.|THIN LAYER CHROMATOGRAPHY DETECTION LIMITS ARE GIVEN FOR 6 XYLENOL ISOMERS ON SILUFOL AND KIESELGEL G USING A 9:1 BENZENE-ACETONE MIXTURE AS THE SOLVENT PHASE & FAST DYEING SALTS AS SPRAY REAGENTS. /XYLENOLS/|ISOLATION OF THE REFERENCE PHENOLS (INCLUDING 3,5-DIMETHYLPHENOL) FROM INTERFERING COMPOUNDS GAVE RELATIVE RECOVERY OF 90-100%. SEPARATION OF PHENOLS INTO INDIVIDUAL COMPONENTS WAS PERFORMED ON POLAR PACKINGS AS WELL AS ON REVERSE PHASE PACKINGS. QUANTITATIVE ANALYSIS WAS CARRIED OUT ON A PREPACKED ZORBAX ODS COLUMN USING A UV PHOTOMETER OF 254 NM WAVELENGTH. THE CONCENTRATIONS OF THE PHENOLS DETERMINED BY HPLC WERE 1-10 PPM OR 0.03-0.18 MG/CU M OF AUTO EXHAUST.|A HIGH PERFORMANCE LIQ CHROMATOGRAPHIC METHOD FOR DETERMINING PHENOL, CRESOLS & XYLENOLS IN COAL GASIFIER CONDENSATES IS PRESENTED. ALIQUOTS OF CONDENSATE ARE INJECTED DIRECTLY ONTO REVERSE-PHASE HPLC SYSTEM & EFFLUENT MONITORED BY UV ABSORBANCE AT 215 NM. /XYLENOLS/|For more Analytic Laboratory Methods (Complete) data for 3,5-DIMETHYLPHENOL (10 total), please visit the HSDB record page.

A proposed method for simultaneously determining phenol, cresols, xylenol isomers, and naphthols in urine samples utilizing solid phase excretion and capillary gas chromatography was developed.|/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
XLogP3:2.4
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:80.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

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