3,5-Xylenol

log Kow= 2.35

2.35

2.54

0.968 at 68 °F (NTP, 1992) - Less dense than water; will float

0.9680 @ 20 °C/4 °C

0.97 g/cm³

Needles from water

Needles from petroleum ether

White crystals

less than 1 mg/mL at 68 °F (NTP, 1992)

Sol in ethyl alcohol, carbon tetrachloride

Very sol in benzene, chloroform, ether

In water, 4.88X10+3 mg/l @ 25 °C.

4.0 x 10 (-2) mol/l, at pH 5.1 and 25 °C.

Solubility in water, g/100ml at 25 °C: 0.5

[HSDB] 80 °C

80 °C c.c.

427.1 °F at 760 mmHg (NTP, 1992)

219.5 °C

219 °C

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P260, P262, P264, P270, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P361+P364, P363, P405, and P501 (click each P-code to see the statement)

Danger

H301 (99.7%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P262, P264, P264+P265, P270, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P361+P364, P362+P364, P363, P405, and P501 (click each P-code to see the statement)

Chemical: Phenol, 3,5-dimethyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Phenol, 3,5-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 3,5-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 24-03-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/1918

Phenol, 3,5-dimethyl-: Does not have an individual approval but may be used under an appropriate group standard

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

Combustible. Finely dispersed particles form explosive mixtures in air.

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.

Causes ataxia and muscle contraction/spasticity in lethal-dose testing of mice; [RTECS] Toxic by ingestion; A severe eye irritant; [HSDB] A corrosive substance that can cause injury to the skin and eyes; A respiratory tract irritant; [ICSC] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; May be absorbed through skin; [MSDSonline] As the six dimethylphenol isomers and the mixed isomer substance are generally similar in toxicity, a common TLV for these substances is appropriate. . . . In mice, oral exposure to 250 mg/kg/day produced changes in blood parameters including statistically significant decreases in mean corpuscular volume and mean corpuscular hemoglobin concentration (4 and 3% reduction in mean values, respectively. . . . Available data on skin sensitization from exposure to dimethylphenol are mixed but warrant the addition of a DSEN notation. . . . All six dimethylphenol isomers were tested in a mouse local lymph node assay and the results found 2.4, 2,5, and 3,4-dimethylphenol to be positive for skin sensitization. There are no epidemiology studies. In a case report, ingestion of about 250 ml of a mixture of dimethylphenol isomers resulted in CNS depression, hypotension, and death. [ACGIH] See Phenol.

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.

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.

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.

Rest. Do NOT induce vomiting. Refer for medical attention .

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.

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.

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.)

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.

LC100 Tetrahymena pyriformis (protozoa ciliate) 2.3 mmole/l/24 hr /Conditions of bioassay not specified/

TLm Carassius carassius (Crucian carp) 53 mg/l/24 hr /Conditions of bioassay not specified/

TLm Tinca tinca (tench) 52 mg/l/24 hr /Conditions of bioassay not specified/

TLm Salvelinus (trout embryos) 50 mg/l/24 hr /Conditions of bioassay not specified/

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).

Cough. Dizziness. Headache.

MAY BE ABSORBED! Burning sensation. Skin burns.

Redness. Pain. Severe deep burns.

Burning sensation. Abdominal pain. Nausea. Vomiting. Diarrhoea. Dizziness. Headache. Shock or collapse.

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).

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).

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).

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).

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/

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.

Used as a chemical intermediate for biocides, antioxidants, pharmaceuticals, herbicides, phenolic resins, Metaxalone (muscle relaxant), and methyl carbamate derivatives for insecticides; [HSDB]

CHEM INTERMEDIATE FOR P-CHLORO- AND 2,4-DICHLORO-M-XYLENOL-BIOCIDES.

CHEM INTERMEDIATE FOR METAXALONE USED AS A MUSCLE RELAXANT.

CHEM INTERMEDIATE FOR METHYL CARBAMATE DERIVATIVES FOR INSECTICIDES.

CHEM INTERMEDIATE FOR GASOLINE ANTIOXIDANTS (ISOMERIC MIXT).

For more Uses (Complete) data for 3,5-DIMETHYLPHENOL (10 total), please visit the HSDB record page.

2023: 3,505,736 lb

(1977) AT LEAST 4.99X10+8 G

(1981) PROBABLY GREATER THAN 2.27X10+6 G

FRACTIONAL DISTILLATION OF CRUDE COAL TAR ACIDS; DEMETHYLATION OF 3,5,5-TRIMETHYL-2-CYCLOHEXENE-1-ONE (ISOPHORONE).

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/

Dealkylation/dehydrogenation of isophorone; sulphonation/alkali fusion of m-xylene

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/

Oil and Gas Drilling, Extraction, and Support activities

Phenol, 3,5-dimethyl-: ACTIVE