3,4-Dimethylphenol

log Kow= 2.23

2.23

2.37

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

0.983 @ 20 °C/4 °C

Needles from water

Prisms from ligroin

Danger

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

P260, P262, P264, P270, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P361+P364, P363, P391, P405, and P501 (click each P-code to see the statement)

Danger

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

P260, P261, P262, P264, P264+P265, P270, P272, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P333+P317, P361+P364, P362+P364, P363, P391, P405, and P501 (click each P-code to see the statement)

Chemical: Phenol, 3,4-dimethyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com.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

Phenol, 3,4-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 3,4-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: 17-12-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/30340

3,4-Dimethylphenol: Does not have an individual approval but may be used under an appropriate group standard

SYMPTOMS: Symptoms of exposure to this compound may include 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 corrosion of the mucous membranes, upper respiratory tract, skin, and eyes. Inhalation may be fatal as a result of spasm, inflammation and edema of the larynx and bronchi; chemical pneumonitis; and pulmonary edema. Chronic exposure may cause liver or kidney damage.

Safe when used as a flavoring agent in food; [JECFA] Causes tetany, hepatitis, and renal tubular changes in lethal-dose feeding studies of rats; [RTECS] Toxic by ingestion; [HSDB] Corrosive to tissues; May cause spasm, inflammation, and edema of the larynx and bronchi after inhalation; Can cause liver and kidney damage; [CAMEO] May cause burns; [eChemPortal: ESIS] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; May be absorbed through skin; Effects in high-dose animal studies include acute tubular necrosis and hepatitis; [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.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 3,4-Dimethylphenol is included on this list.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble in 51 FR 41329.

/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 3,4-DIMETHYLPHENOL (8 total), please visit the HSDB record page.

Acute Tox. 3 (99.7%)

Acute toxicity - category 3

Acute toxicity (Oral) - Category 4

Acute toxicity (Oral) - Category 4

Acute Tox. 3 *

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.

The effectiveness of anaerobic filters containing granular activated carbon in treating synthetically prepared wastewaters which contained phenols, polycyclic hydroxy compounds, monocyclic n-aromatics, polycyclic n-aromatics, and 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.

Chemical Treatability of 3,4-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: 95.5% reduction based on chemical oxygen demand; rate of biodegradation 13.4 mg chemical oxygen demand/g hr (activated sludge process).

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.

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/

Wear appropriate chemical protective gloves, boots and goggles.

TLm Carassius carassius (Crucian carp) 21 mg/l/24 hr /Conditions of bioassay not specified/

TLm Rutilus rutilus (roach) 16 mg/l/24 hr /Conditions of bioassay not specified/

TLm Tinca tinca (tench) 18 mg/l/24 hr /Conditions of bioassay not specified/

TLm Salvelinus (trout embryos) 7 mg/l/24 hr /Conditions of bioassay not specified/

For more Ecotoxicity Values (Complete) data for 3,4-DIMETHYLPHENOL (9 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 390(SRC), determined from a log Kow of 2.23(2) and a regression-derived equation(3), indicates that 3,4-dimethylphenol is expected to have moderate mobility in soil(SRC). Volatilization of 3,4-dimethylphenol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-6 atm-cu m/mole(SRC), determined from its vapor pressure of 0.036 mm Hg(4) and water solubility of 4760 mg/l(5). 3,4-Dimethylphenol is not expected to volatilize from dry soil surfaces based upon a its vapor pressure(3). 3,4-Dimethylphenol has been reported to completely biodegrade in soil in 9 days at a temperature of 19 °C(6).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 390(SRC), determined from a log Kow of 2.23(2) and a regression-derived equation(3), indicates that 3,4-dimethylphenol is expected to adsorb very little to suspended solids and sediment in water(SRC). 3,4-Dimethylphenol is expected to volatilize from water surfaces(3,SRC) based upon an estimated Henry's Law constant of 1.2X10-6 atm-cu m/mole(SRC), determined from its vapor pressure of 0.036 mm Hg(4) and water solubility of 4760 mg/l(5). Estimated volatilization half-lives for a model river and model lake are 34 days and 250 days, respectively(3,SRC). According to a classification scheme(6), an estimated BCF of 29(3,SRC), from 3,4-dimethylphenol's log Kow(2), suggests bioconcentration in aquatic organisms is low(SRC). In humic waters, degradation by the reaction with peroxy radicals should ensue with a half-life on the order of hours(7). 3,4-Dimethylphenol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). Screening studies indicate that theoretical oxygen demand reached 43% after 5 days(8,9). In addition, it has been reported that 3,4-dimethylphenol was readily degraded in St. Lawrence River water(10). Biodegradation under anaerobic conditions failed to occur after 24 days from a river sediment inoculum(11).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3,4-dimethylphenol, which has a vapor pressure of 0.036 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3,4-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 4.7 hours(SRC) from its rate constant of 8.14X10-11 cu cm/molecule-sec at 25 °C(3). Atmospheric 3,4-dimethylphenol is known to be removed by rainwater(4). 3,4-Dimethylphenol has an absorption band at 274 nm (water), 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).

3,4-Dimethylphenol was measured in raw waste water from a paper mill at 0.0457 mg/l in 1974, and had been observed at this site in 1972. It was not detected in the treated effluent from the plant(1). 3,4-Dimethylphenol was identified in Los Angeles County, CA effluent (1980-81) at 20 ug/l(2). Waste water from the gasification of Indian Head lignite coal in North Dakota was determined to have an approximate 3,4-dimethylphenol concn of 158 mg/l(3). 3,4-Dimethylphenol was detected in treated refinery effluent (Geelong, Victoria, Australia, 1985) at a concn of 0.02 mg/l(4). 3,4-Dimethylphenol was identified but not quantified in leachate collected from a Swedish municipal landfill in May 1990(5). 3,4-Dimethylphenol was also identified in the leachate from a sanitary landfill in Barcelona, Spain(6).

3,4-Dimethylphenol

Cardiovascular

1 x 10 ^-3 mg/kg-day

The Koc of 3,4-dimethylphenol is estimated as 390(SRC), using a log Kow of 2.23(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 3,4-dimethylphenol is expected to have moderate mobility in soil(SRC). 65.2% of 3,4-dimethylphenol was sorbed onto the high clay content, adsorption activated material Bentone 24 at pH= 7.8; 13% with Bentone 18C at pH 7.7; these values fluctuate as a function of pH(4).

URBAN/SUBURBAN: In 1984, a gas phase concn of 3,4-dimethylphenol was detected in two of seven rain events in Portland, OR, at 5.4 and 3.5 ng/cu m respectively. 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).

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 3,4-Dimethylphenol is included on this list.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble in 51 FR 41329.

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. AFTER THE ADMIN OF 100 MG/KG OF O-XYLENE IN RATS, 0.1% WAS METABOLIZED TO 3,4-DIMETHYLPHENOL.

YIELDS 4,5-DIMETHYLCATECHOL IN RABBITS. YIELDS 3,4-DIMETHYLPHENYL-BETA-D-GLUCURONIDE IN RABBITS. /FROM TABLE/

YIELDS 3,4-DIMETHYLPHENYL SULFATE IN RABBITS & IN RATS. /FROM TABLE/

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.

2,3-Dimethylphenol is a known human metabolite of o-xylene.

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 starting material for phenolic resins; [HSDB]

Starting materials in the phenolic resins. /Xylenols/

3,4-Dimethylphenol is found in coffee and coffee products.

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/

Produced from the hydrolysis of 4-chloro-o-xylene

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Plastics Material and Resin Manufacturing

Phenol, 3,4-dimethyl-: ACTIVE