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Home > Encyclopedia > 2,5-Dimethylphenol

2,5-Dimethylphenol

2,5-Dimethylphenol structure

2,5-Dimethylphenol 

structure
  • CAS No:

    95-87-4

  • Formula:

    C8H10O

  • Chemical Name:

    2,5-Dimethylphenol

  • Synonyms:

    Phenol,2,5-dimethyl-;2,5-Xylenol;2,5-Dimethylphenol;p-Xylenol;1,2,5-Xylenol;1-Hydroxy-2,5-dimethylbenzene;3,6-Dimethylphenol;NSC 2599;2-Hydroxy-p-xylene;50356-12-2;145929-31-3

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

WHITE TO CREAM COLORED CRYSTALS 2,5-Xylenol has a creosote, sweet, medicinal taste.


2,5-dimethylphenol is a colorless to off-white crystalline solid. Odor threshold concentration 0.4 mg/L. Taste threshold concentration 0.5 mg/L. (NTP, 1992)|Liquid|Solid|Colourless crystalline solid; Colourless needles


2,5-dimethylphenol is a colorless to off-white crystalline solid. Odor threshold concentration 0.4 mg/L. Taste threshold concentration 0.5 mg/L. (NTP, 1992)

2,5-Dimethylphenol Basic Attributes

122.164

122.16

202-461-5

XH3E3564KX

2599

2261

DTXSID6025145

Crystals from alcohol plus ether|NEEDLES FROM WATER; PRISMS FROM ALCOHOL-ETHER

2907199090

Characteristics

20.23000

2.40

2,5-dimethylphenol is a colorless to off-white crystalline solid. Odor threshold concentration 0.4 mg/L. Taste threshold concentration 0.5 mg/L. (NTP, 1992)

0.965 g/cm3 @ Temp: 80 °C

74.5 °C

211.5 °C @ Press: 762 Torr

86.7±7.2 °C

1.540

1 g/100 mL (60 ºC)

Keep away from heat, sparks, and flame. Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

0.208 hPa (25 °C)

0.5 mg/l (taste threshold concn)

8.00e-11 cm3/molecule*sec

1.12e-06 atm-m3/mole

pKa= 10.41 at 25 °C|pK = 10.3

Heat of fusion: 23.38 kJ/mole @ 74.8 °C|Dipole moment: 1.43 debye (benzene, 20 °C); 1.52 debye (benzene, 60 °C)|Hydroxyl radical rate constant = 8.00X10-11 cu cm/molc sec @ 25 °C

This chemical is hygroscopic. Insoluble in water.

Phenols and Cresols

2,5-DIMETHYLPHENOL is incompatible with bases, acid chlorides, acid anhydrides and oxidizing agents. It corrodes steel, brass, copper and copper alloys. (NTP, 1992)

13,130.2 g cal/g mole

Safety Information

II

6.1

UN 2261 6.1/PG 2

3

R24/25;R34;R51/53

S26-S36/37/39-S45-S61

ZE5775000

T:Toxic;N:Dangerousfortheenvironment;

Stable under normal temperatures and pressures.

P273-P280-P301 + P310-P305 + P351 + P338-P310

H301-H311-H314-H411

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 2,5-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: 94.5% reduction based on chemical oxygen demand; rate of biodegradation 10.6 mg chemical oxygen demand/g hr (activated sludge process).

EPA. EPA/600/8-88/031 p.30 (1987). Health effects assessment for dimethylphenols.|Center for Chemical Hazard Assessment SRC TR 81-527, Second draft (1981). Information profiles on potential occupational hazards: xylenols.

Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)

|Danger|H301 (99.78%): 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 2313 companies from 13 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|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

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/

FOUNDRY PLANT WASTE GASES WERE DEODORIZED WITH POTASSIUM PERMANGANATE, AND DEODORIZATION EFFICIENCY WAS MEASURED BY PRESENCE OF 2,5-XYLENOL IN SCRUBBED WASTE GASES.

/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 2,5-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.

2,5-Dimethylphenol was identified in Los Angeles County, CA effluent (1980-81) at 10 ug/l(1). Waste water from the gasification of Indian Head lignite coal in North Dakota was determined to have an estimated 2,5-dimethylphenol concentration of 358 mg/l(2). 2,5-Dimethylphenol was detected but not quantified in low temperature carbonization wastewater collected in Naspur, India(3).

2,5-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 2,5-dimethylphenol was detected in 7 of 7 rain events in Portland, OR, at concns ranging from 15-70 ng/cu m, averaging 33 ng/cu m, analyzed as a mixture with 2,4-dimethylphenol(1). The amount associated with adsorption to particulate matter was <5% of the gas phase concn in every case(1). Not detected in either rural or urban air samples (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).

IDENTIFIED IN PARTICULATE PHASE OF TOBACCO SMOKE: 2,4- AND 2,5-DIMETHYLPHENOLS, 2000 UG/100 CIGARETTES. /FROM TABLE/|2,5-Dimethylphenol was identified as a component of cigarette smoke, with concentrations ranging from 0.7 to 2.1 mg/100 cigarettes (analyzed with 2,4-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 2,5-XYLENOL.

LD50 Rat oral 444 mg/kg|LD50 Mouse oral 383 mg/kg|LD50 Rabbit oral 938 mg/kg

2,5-Dimethylphenol has been found in tobacco(1-3) and marijuana mainstream smoke(3), and black tea(4).

/SRP/: 2,5-DIMETHYLPHENOL IS A CONSTITUENT OF ... AUTOMOBILE EXHAUST, AND SHALE OIL WASTE WATER.|2,5-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 a raw material for antioxidants in gasoline and rubber(3), and as a component of automobile and diesel exhaust(4-7) may result in its release to the environment through various waste streams(SRC). Dimethylphenols, of which 2,5-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), an estimated Koc value of 440(SRC), determined from a log Kow of 2.33(2) and a regression-derived equation(3), indicates that 2,5-dimethylphenol is expected to have moderate mobility in soil(SRC). Volatilization of 2,5-dimethylphenol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.1X10-6 atm-cu m/mole(SRC), determined from its vapor pressure of 0.156 mm Hg(4) and water solubility of 3540 mg/l(5). 2,5-Dimethylphenol is not expected to volatilize from dry soil surfaces based upon its vapor pressure(3). 2,5-Dimethylphenol has been reported to biodegrade in soil in 14 days at a temperature of 19 °C(6). Biodegradation under anaerobic conditions failed to occur in one study using a river sediment inoculum, time unspecified(7), yet 55% degradation occurred after 8 weeks in another study using a contaminated groundwater digester(8).|AQUATIC FATE: Based on a classification scheme(1), a Koc value of 440(SRC), determined from a log Kow of 2.33(2) and a regression-derived equation(3), indicates that 2,5-dimethylphenol is expected to adsorb very little to suspended solids and sediment in water(SRC). 2,5-Dimethylphenol is expected to volatilize from water surfaces(3,SRC) based upon an estimated Henry's Law constant of 7.1X10-6 atm-cu m/mole(SRC), determined from its vapor pressure of 0.156 mm Hg(4) and water solubility of 3540 mg/l(5). Estimated volatilization half-lives for a model river and model lake are 6 days and 46 days, respectively(3,SRC). According to a classification scheme(6), an estimated BCF of 35(3,SRC), from 2,5-dimethylphenol's log Kow(2), 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). 2,5-Dimethylphenol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). The rate of biodegradation obtained for 2,5-dimethylphenol in a screening test with an adapted activated sludge seed was 94.5% chemical oxygen demand after 5 days(8). In addition, it has been reported that 2,5-dimethylphenol was readily degraded in St. Lawrence River water(9). Biodegradation under anaerobic conditions failed to occur in one study, time unspecified(10), yet 55% degradation occurred after 8 weeks in another study(11).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,5-dimethylphenol, which has a vapor pressure of 0.156 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,5-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 4.8 hours(SRC) from its rate constant of 8.00X10-11 cu cm/molecule-sec at 25 °C(3). Atmospheric 2,5-dimethylphenol is known to be removed by rainwater(4). 2,5-Dimethylphenol has an absorption band at 276 nm (alcohol-ether), 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 2,5-dimethylphenol with photochemically-produced hydroxyl radicals has been determined to be 8.00X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 4.8 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). 2,5-Dimethylphenol has an absorption band at 276 nm (alcohol-ether), 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). 2,5-Dimethylphenol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3).

An estimated BCF of 35 was calculated for 2,5-dimethylphenol(SRC), using a log Kow of 2.33(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.

The Koc of 2,5-dimethylphenol is estimated as 440(SRC), using a log Kow of 2.33(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,5-dimethylphenol is expected to have moderate mobility in soil(SRC).

The Henry's Law constant for 2,5-dimethylphenol is estimated as 7.1X10-6 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 0.156 mm Hg(1), and water solubility, 3540 mg/l(2). This Henry's Law constant indicates that 2,5-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 6 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 46 days(SRC). 2,5-Dimethylphenol's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces is expected to occur(SRC). 2,5-Dimethylphenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.156 mm Hg(1).

GROUNDWATER: 2,5-Dimethylphenol was found in concns ranging from 1-130 ug/l in 4 out of 4 up-gradient wells, and 1,800-9,400 ug/l in 6 out of 7 down-gradient wells near a former pine-tar manufacturing facility in Gainesville, FL, analyzed as a mixture with 3,4-dimethylphenol(1). Studies near a closed wood preserving facility in Pensacola, FL detected 2,5-dimethylphenol in groundwater ranging from 3.04 mg/l at 6 m depth and 2.55 mg/l at 18 m depth approximately 170 m from the plant site; at approximately 330 m from the site, 0.57 mg/l 2,5-dimethylphenol was detected at a depth of 6 m and 0.33 mg/l was detected at a depth of 12 m(2). The concn of 2,5-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 6.24 mg/l and 0.56 mg/l, respectively(3). Groundwater samples collected from three creosote-contaminated sites in Denmark, date unspecified, were found to contain 2,5-dimethylphenol ranging in concn from below detection to 2090 ug/l(4). 2,5-Dimethylphenol was detected at a concn of 0.1 mg/l in groundwater near an abandoned wood preservative manufacturing plant in Florida(5). Water samples collected during December 1986 from Gas Works Park, Seattle, WA were found to contain 2,5-dimethylphenol ranging in concn from below detection to 1.5 mg/l(6).|SURFACE WATER: 2,5-Dimethylphenol was qualitatively identified in samples from the Saint Lawrence River(1).|RAIN/SNOW: In 1984, 2,5-dimethylphenol was detected in seven rain events in Portland, OR, with concns ranging from 300-1300 ng/l and averaging 820 ng/l; analyzed as a mixture with 2,4-dimethylphenol(1).

2,5-Dimethylphenol was identified as a volatile component of fresh tree-ripened apricots (Prunus armeniaca L.) with a concn of 33 mg/kg fresh fruit tissue(1). 2,5-Dimethylphenol was identified as a volatile flavor component of the Japanese dried food, Bonito(2).

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 2,5-dimethylphenol may occur through inhalation of this compound at workplaces where 2,5-dimethylphenol is produced or used(SRC). The general population may be exposed to 2,5-dimethylphenol via inhalation of ambient air (i.e., tobacco smoke(2) and automobile exhaust(3)), ingestion of food(4,5), and contact with other products that may contain 2,5-dimethylphenol(SRC).

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.|Phenol (87.3 mg/l), p-cresol (58.6 mg/l), o-cresol (76.9 mg/l), and 2,5-xylenol (36.7 mg/l) were detected in the urine of workers employed in the distillation of the high temperature phenolic fraction of tar (carbolic oil). The concentrations of these compounds in the urine of non-exposed male workers was 11.7 mg/l, 25.7 mg/l, 68.1 ug/l, and 69 ug/l respectively. The excretion rates were 4.20 mg/hr for phenol, 2.4 mg/hr for p-cresol, 3.3 mg/hr for o-cresol; and 1.5 mg/hr for 2,5-xylenol. The highest concentrations of the ... compounds were detected in urine collected between eight and 10 hr from the beginning of exposure. ...

YIELDS 2,5-DIMETHYLPHENYL-BETA-D-GLUCURONIDE AND 2,5-DIMETHYLPHENYL SULFATE IN RABBITS; 3-HYDROXY-4-METHYLBENZOIC ACID IN PSEUDOMONAS. /FROM TABLE/|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. P-XYLENE ADMINISTERED AT A DOSE OF 100 MG/KG WAS METABOLIZED TO 2,5-DIMETHYLPHENOL TO THE EXTENT OF 1.0% OF THE DOSE GIVEN.|FOUR PERSONS WERE EXPOSED TO XYLENES. 2,3- AND 3,4-XYLENOL WERE OBSERVED IN URINE OF THOSE EXPOSED TO O-XYLENE. 2,4-XYLENOL OBSERVED AFTER M-XYLENE AND 2,5-XYLENOL AFTER P-XYLENE.|Pulmonary metabolites of p-xylene, p-methylbenzyl alcohol and 2,5-dimethylphenol, were employed to investigate the divergent effects of p-xylene on pulmonary and hepatic metabolism. Rats were given p-methylbenzyl alcohol, 2,5-dimethylphenol, or 10% cremophore (control) ip daily for 3 days, and effects on hepatic and pulmonary microsomal metabolism were determined 12 hours later. Both p-methylbenzyl alcohol and 2,5-dimethylphenol mimic the decrease in pulmonary benzyloxyresorufin-O-debenzylase activity previously reported for p-xylene, but neither could account for the potent induction of cytochrome P450 in the liver. Only p-methylbenzyl alcohol had a consistent effect on P450IIB apoprotein levels, decreasing them in both the liver and lung. These data suggest that p-methylbenzyl alcohol may have a significant role in the inhibition of pulmonary P450 caused by p-xylene.|2,5-dimethylphenol is a known human metabolite of p-xylene.

SYMPTOMS: Symptoms of exposure to this compound may include severe irritation and burns of the skin and eyes; irritation of the respiratory tract, dizziness, stomach pain, exhaustion, coma and damage to the liver or kidneys. Other symptoms include headache, nausea and vomiting. It may cause corrosion of the tissues of the mucous membranes and upper respiratory tract, eyes and skin. Inhalation may result in burning sensation, coughing, wheezing, laryngitis and shortness 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 skin sensitization, profuse sweating, painless blanching or erythema of the skin, intense thirst, diarrhea, cyanosis from methemoglobinemia, hyperactivity, stupor, blood pressure fall, 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 chemical is highly toxic by inhalation, ingestion or skin absorption. It is corrosive to tissue of the mucous membranes and 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. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 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)

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/|LISTED AS A TUMOR PROMOTER. /FROM TABLE/

2,5-dimethylphenol

2,5-Dimethylphenol Use and Manufacturing

Methods of Manufacturing

The insertion of methyl groups into phenol to produce ... xylenols is a commercial process of considerable utility. The process commomly 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/

Uses

Processing aids, not otherwise listed


Cleaning and furnishing care products

Production

1,000,000 - 10,000,000 lb

Xylenol 100; a high purity fraction of 2,4- and 2,5- xylenol (ortho xylenols); typical composition: 2,4- and 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/

All other chemical product and preparation manufacturing|Phenol, 2,5-dimethyl-: ACTIVE

THE ANALYTICAL CONDITIONS UNDER WHICH XYLENOLS ARE DETERMINED ALONG WITH OTHER PHENOLS FOR THE CHARACTERIZATION OF PETROLEUM WASTE DISCHARGES USING DINONYL PHTHALATE COLUMNS ARE DISCUSSED. /XYLENOLS/|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/|TRACES OF PHENOLS (INCLUDING 2,5-DIMETHYLPHENOL) IN AUTO EXHAUST AND TOBACCO SMOKE WERE COLLECTED USING A FRITTED BUBBLER WITH 10 ML 0.12% SODIUM HYDROXIDE SOLUTION AND DETERMINED BY REVERSED-PHASE HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY VIA DERIVATIZATION WITH P-NITROBENZENEDIAZONIUM TETRAFLUORIDE IN AQUEOUS MEDIUM AT PH 11.5. THE DETECTION LIMITS OF THE PHENOLS WERE 0.005-2.0 NG.|THE SENSITIVE DETECTION OF PHENOLS REMAINS A PROBLEM IN TOXICOLOGICAL AND PESTICIDAL ANALYSES. 2,5-XYLENOL WAS CONVERTED INTO THE CORRESPONDING BROMOPHENOL BY REACTION WITH BROMINE. THE MINIMUM DETECTABLE AMOUNT OF THE BROMOPHENOLS WITH AN ELECTRON CAPTURE DETECTOR WAS ABOUT 0.01 NG, WHICH IS ABOUT 100 TIMES LESS THAN THE MINIMUM DETECTABLE AMOUNT OF THE NON-BROMINE-CONTAINING PHENOLS.|For more Analytic Laboratory Methods (Complete) data for 2,5-DIMETHYLPHENOL (8 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 -> JECFA Flavorings Index

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

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