2,4-Dimethylphenol

Pesticide -> EPA IRIS

Semi-Volatile Organic Compound (SVOC) (Pesticide)

log Kow= 2.30

2.3

2.48

1.0276 at 57 °F (NTP, 1992) - Denser than water; will sink

0.9650 @ 20 °C/4 °C

0.97 g/cm³

0.9650 @ 20°C

Crystals

NEEDLES FROM WATER

Colorless needles

less than 1 mg/mL at 64 °F (NTP, 1992)

Miscible in ethyl alcohol, ethyl ether; soluble in carbon tetrachloride

Very sol in benzene, chloroform

In water, 7.87X10+3 mg/l @ 25 °C.

Soluble in oxygenated and aromatic solvents

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

greater than 235 °F (NTP, 1992)

Flash point > 112 °C

>112 °C (closed cup)

>112 °C c.c.

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 (99.1%): 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, 2,4-dimethyl-

Hazard Traits - Hematotoxicity; Neurotoxicity

Commission Regulation (EC) No 1565/2000 (Repealed by Com.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

Phenol, 2,4-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2,4-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: 18-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/33125

2,4-Xylenol: Does not have an individual approval but may be used under an appropriate group standard

This chemical is probably combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

SYMPTOMS: Symptoms of exposure to this compound may include severe irritation of the skin and eyes, dizziness, stomach pain, exhaustion and damage to the liver and kidneys. Other symptoms include headache, nausea and vomiting. It may cause severe burns of the eyes and skin, irritation of the respiratory tract and coma. It may also cause corrosion of tissue of the mucous membranes and upper respiratory tract, eyes and skin. Inhalation may result in burning sensation, coughing, wheezing, laryngitis and short ness of breath. Inhalation may be fatal as a result of spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis and pulmonary edema. Symptoms of exposure to this class of compounds include profuse sweating, skin sensitization, painless blanching or erythema of the skin, intense thirst diarrhea, cyanosis from methemoglobinemia, hyperactivity, stupor, fall in blood pressure, hyperpnea, abdominal pain, hemolysis and convulsions. If death from respiratory failure is not immediate, jaundice and oliguria or anuria may occur.

A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; May cause pulmonary edema; May cause skin sensitization; [ICSC] Corrosive to tissues; Inhalation may cause laryngeal spasm, edema of the bronchi, and chemical pneumonitis; May induce methemoglobinemia and injury to the liver and kidneys; [CAMEO] 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.

USEPA; Ambient Water Quality Criteria Doc: 2,4 Dimethylphenol (1980) EPA 440/5-80-044.

Toxikologische Bewertung. 137 (1995). Summary and assessment of 2,4-xylenol.

EPA. EPA/600/8-88/031 p.30 (1987). Health effects assessment for dimethylphenols.

Tucker JD et al; Mutat Res 297 (2): 101-80 (1993). Sister-chromatid exchange: second report of the Gene-Tox Program.

U101; As stipulated in 40 CFR 261.33, when 2,4-dimethylphenol, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

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.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. 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: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U101, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.

A pilot plant study was conducted to evaluate the fate and behavior of 22 toxic organic compounds in conventional activated sludge wastewater treatment plants. The organic cmpd, 2,4-dimethylphenol, spiked at a nominal concn of 50 ug/l was about 99% removable. Results showed that biodegradability was variable and was a function of molecular structure.

The effectiveness of anaerobic filters containing granular activated carbon in treating synthetically prepared wastewaters that contained phenols, polycyclic hydroxy compounds, monocyclic N-aromatics, polycyclic N-aromatics, & aliphatic acids was evaluated. The ability of the activated carbon to retain these compounds along with its external surface, which provides vast sheltered microbial attachment areas, renders activated carbon a very unique medium for anaerobic filter treatment of coal gasification wastewater.

For more Disposal Methods (Complete) data for 2,4-DIMETHYLPHENOL (6 total), please visit the HSDB record page.

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. If liquid: collect leaking liquid in covered plastic containers.

LC50 Pimephales promelas (fathead minnow) 17 mg/l/96 hr /Flow through bioassay/

TLm Carassius carassius (crucian carp) 30 mg/l/24 hr /Conditions of bioassay not specified/

LC50 Pimephales promelas (fathead minnow) 16.6 mg/l/96 hr (confidence limit 16.1-17.1 mg/l) at 25.6 °C (hardness 45.7 mg/l CaCO3, pH 8.25) /Conditions of bioassay not specified/

LC50 Pimephales promelas (fathead minnow) 13,650 ug/l/192 hr /Static, unmeasured bioassay/

For more Ecotoxicity Values (Complete) data for 2,4-DIMETHYLPHENOL (9 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 430(SRC), determined from a log Kow of 2.30(2) and a regression-derived equation(3), indicates that 2,4-dimethylphenol is expected to have moderate mobility in soil(SRC). Volatilization of 2,4-dimethylphenol from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.7X10-5 atm-cu m/mole (4). 2,4-Dimethylphenol is not expected to volatilize from dry soil surfaces(3) based upon a vapor pressure of 0.102 mm Hg at 25 °C(5). 2,4-Dimethylphenol has been reported to completely biodegrade from soil in 4 days at a temperature of 19 °C(6) and the biodegradation half-life of 2,4-dimethylphenol from Texas soil and Mississippi soil was determined to be 1.5 and 3.5 days, respectively(7).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 430(SRC), determined from a log Kow of 2.30(2) and a regression-derived equation(3), indicates that 2,4-dimethylphenol is expected to adsorb very little to suspended solids and sediment in water(SRC). 2,4-Dimethylphenol is expected to volatilize from water surfaces(3,SRC) based upon a Henry's Law constant of 1.7X10-5 atm-cu m/mole(4). Estimated volatilization half-lives for a model river and model lake are 3 days and 22 days, respectively(3,SRC). According to a classification scheme(5), a BCF of 150 in bluegill sunfish(6) suggests bioconcentration in aquatic organisms is moderate(SRC). In humic waters, degradation by the reaction with peroxy radicals should ensue with a half-life on the order of hours(7). 2,4-Dimethylphenol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). Screening studies indicate that 95% removal of 2,4-dimethylphenol was obtained after 5 days using an activated sludge inoculum(8). In addition, it has been reported that 2,4-dimethylphenol was readily degraded in St. Lawrence River water(9). Methanogenic consortia failed to anaerobically biodegrade 2,4-dimethylphenol after 24 days in one study(10); in two standardized anaerobic bioassays using a digester sludge, 2,4-dimethylphenol yielded no more than 10% of theoretical methane(11).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4-dimethylphenol, which has a vapor pressure of 0.102 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,4-dimethylphenol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 5.3 hours(SRC) from its rate constant of 7.20X10-11 cu cm/molecule-sec at 25 °C(3). 2,4-Dimethylphenol has an absorption band at 296 nm (maximum) and extends over 320 nm, thus making it a candidate for direct photochemical degradation(5,6). Night-time degradation in urban areas should occur rapidly through reaction with atmospheric nitrate radicals, as rate constants for this reaction with phenolic compounds are approximately 250 times faster than with hydroxyl radicals(7,SRC).

A field study of industrial organic uptake by growing crops was conducted during 1990 at the St. David Coal Refuse Pile Reclamation Site, Fulton County, IL; 2,4-dimethylphenol was detected in coal refuse and plant materials, concns unknown(1).

Burning sensation. Cough. Sore throat. Shortness of breath.

Redness. Pain. Skin burns.

Redness. Pain. Severe burns.

Burning sensation. Abdominal pain. Nausea. Vomiting. Shock or collapse.

2,4-Dimethylphenol was detected in raw sludge and treated sludge, concns unknown, in samples taken from 37 water pollution control plants in Ontario, Canada between January and July 1986(1). Waste water from the gasification of Indian Head lignite coal in North Dakota was determined to have an estimated 2,4/2,5-dimethylphenol concn of 368 mg/l(1). A summary of analysis for 2,4-dimethylphenol in effluent reports that it was found 3 times in residential, 8 times in industrial, and 2 times in commercial effluent, with an overall source average discharge concn of 0.7, 0.0, and 74.0 ug/l, respectively(3). 2,4-Dimethylphenol was identified but not quantified in leachate collected from a Swedish municipal landfill in May 1990(4). Groundwater and soil from 91 waste sites at 18 Department of Energy (DOE) facilities were analyzed; 2,4-dimethylphenol was found at one of the facilities in groundwater, concn not quantified(5).

2,4-Dimethylphenol was found in six effluents in an EPA survey (4000 samples) of effluents covering 46 industrial categories(1). Industries with positive levels of 2,4-dimethylphenol included iron and steel manufacturing, petroleum refining, organics and plastics, rubber processing, organic chemicals, and publicly owned treatment works(1). 2,4-Dimethylphenol was detected in 3.4% of 1321 effluent samples reported in STORET, EPA's water quality data base (1975-82)(2) and, in two out of five effluents of hazardous waste incinerators(3) and at 10 ug/l in urban runoff in Washington, DC(4). This constituted a 2% frequency of detection in the National Urban Runoff Program, which examined 86 runoff samples from 15 USA cities(4). The final effluent of Los Angeles County Municipal Wastewater Treatment Plant was found to contain 5 and <10 ppb 2,4-dimethylphenol in July 1978 and Nov 1980, respectively(5). Of 18 advanced water treatment effluents analyzed, 2,4-dimethylphenol was found in effluents at Lake Tahoe, CA (2 ng/l) and Blue Plains, WA (1 and 8.9 ng/l)(6).

2,4-Dimethylphenol

Hematologic

2 x 10 ^-2 mg/kg-day

U101; As stipulated in 40 CFR 261.33, when 2,4-dimethylphenol, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Toxic pollutant designated pursuant to section 307(a)(1) of the Clean Water Act and is subject to effluent limitations.

Sufficient data are not available for 2,4-dimethylphenol to derive a level which would protect against the potential toxicity of this compound. Using available organoleptic data, for controlling undesirable taste and odor quality of ambient water, the estimated level for 2,4-dimethylphenol is 400 ug/l. It should be recognized that organoleptic data as a basis for establishing a water quality criterion have limitations and have no demonstrated relationship to potential adverse human health effects.

(CA) CALIFORNIA 100 ug/l

(FL) FLORIDA 400 ug/l

(MN) MINNESOTA 100 ug/l

METABOLISM OF 2,4-DIMETHYLPHENOL IN ANIMALS IS VERY SIMILAR TO THAT OF CRESOLS ... .

Rats were admin 2,4-dimethylphenol for 6 hr constantly by iv infusion or iv bolus injection. 2,4-Dimethylphenol was rapidly metabolized to its conjugates (94.3%) within 30 min; the glucuronide constituted 53% and other conjugates 41% /in plasma/.

IN WORKERS SIMULTANEOUSLY EXPOSED TO ETHYLBENZENES AND XYLENES, 2,4-DIMETHYLPHENOL, A METABOLITE OF M-XYLENE, COULD NOT BE DETECTED.

HYDROXYLATION OF AROMATIC HYDROCARBONS WAS STUDIED FOLLOWING THEIR ORAL ADMINISTRATION TO RATS THAT ALSO RECEIVED A PURIFIED DIET CONTAINING NEOMYCIN TO REDUCE THE LEVELS OF NORMALLY OCCURRING SIMPLE URINARY PHENOLS. PHENOLIC METABOLITES WERE QUANTITATIVELY ESTIMATED IN HYDROLYZED URINE SAMPLES BY GAS CHROMATOGRAPHY. M-XYLENE ADMINISTERED AT A DOSE OF 100 MG/KG WAS METABOLIZED TO 2,4-DIMETHYLPHENOL TO THE EXTENT OF 0.9% OF THE DOSE GIVEN.

For more Metabolism/Metabolites (Complete) data for 2,4-DIMETHYLPHENOL (6 total), please visit the HSDB record page.

2,4-Dimethylphenol is a known human metabolite of m-xylene.

SUBJECTS WERE EXPOSED TO M-XYLENE AT CONCN OF ABOUT 3.9 MMOL/CU M FOR 5 DAYS, 6 HR/DAY. RATE OF 2,4-XYLENOL EXCRETION SHORTLY AFTER EXPOSURE WAS ABOUT 1-2% OF THAT FOR METHYLHIPPURIC ACID EXCRETION AND PULMONARY EXCRETION OF UNCHANGED XYLENE WAS ABOUT 4% OF UPTAKE.

The concn of 2,4-dimethylphenol was determined /in/ several tissues of the rat after 6 hr constant iv infusion and after iv bolus injection. 2,4-dimethylphenol was distributed rapidly in the brain and liver, /and had/ high tissue-plasma concn ratios for the brain, liver, and fat. Accumulation of 2,4-dimethylphenol in these tissues was negligible.

FOLLOWING IV ADMIN OF 17 MG/KG OF THE 2,4-ISOMER TO RATS, THE BRAIN ACCUMULATED THE HIGHEST AMT ON A PER G BASIS, FOLLOWED BY FAT AND LIVER. RATIOS OF BRAIN, LIVER AND FAT TO PLASMA /CONCN/ WERE APPROX 1, 1.5 AND 2, RESPECTIVELY.

2,4-DIMETHYLPHENOL DISTRIBUTED RAPIDLY THROUGH THE BODY AFTER IV BOLUS ADMIN OF 30 MG/KG. PLASMA, LIVER AND FAT CONCN DISAPPEARED PRIOR TO 60 MIN BUT PERSISTED IN THE BRAIN.

Associations between o-cresol, p-cresol, m-cresol, 2,4-xylenol, 2,5-xylenol, 3,4-xylenol, and 3,5-xylenol exposure levels and urinary phenol excretion were examined in the coke facility industry. The subjects consisted of 76 exposed workers employed in the tar distillation process and 34 controls. ... Urinary metabolite levels were corrected for specific gravity and creatinine. The time weighted average exposure concentrations in the breathing zones of the tar distillation workers were ... 0.02 to 0.04 mg/cu m for xylenols. ... The urinary xylenol levels of exposed workers ranged from 0.12 to 0.97 mg/l with specific gravity correction. In control urine samples, the specific gravity corrected xylenol concentrations ranged from 25 x 10(-3) to 43 x 10(-3) mg/l. Significant correlations were observed between the ambient levels and urinary concentrations of phenol, o-cresol, and the xylenols, with coefficients ranging from 0.45 to 0.82. The author concludes that the biological monitoring of urinary xylenols may be used as a means of measuring xylenol exposure in coke facility workers.

Used to make phenolic antioxidants, pharmaceuticals, plastics, resins, solvents, insecticides, fungicides, rubber chemicals, polyphenylene oxide, wetting agents, and dyestuffs; Also used as a disinfectant, bacteriocide, germicide, sanitizer, virucide, insecticide, miticide, and fungicide; [HSDB]

Using Disinfectants or Biocides [Category: Clean]

MANUFACTURE OF PHARMACEUTICALS, PLASTICS, INSECTICIDES, FUNGICIDES, RUBBER CHEM, WETTING AGENTS, DYESTUFFS.

HORTICULTURAL FORMULATION FOR ERADICATION OF CROWN GALL TUMORS.

Used in phosphate esters, alkylated xylenols, antioxidants. /Xylenol 100/

Used in the production of high-viscosity phosphate esters, as a feedstock for hindered phenol antioxidant and specialty modified phenolic resin manufacture. /Xylenol 410/

(1977) AT LEAST 4.54X10+7 G

(1982) 5.28X10+7 G (PRINCIPAL CUSTOMS DISTRICTS)

(1983) 1.06X10+8 g

2023: 8,500,000 - <25,000,000 lb

(1977) AT LEAST 9.99X10+8 G

Coal tar fractionation; processing.

The insertion of methyl groups into phenol to produce ... xylenols is a commercial process of considerable utility. The process commonly employed is methylation with methyl alcohol over a solid catalyst, generally a modified metal oxide, at temp in the range of 300-450 °C. /Xylenols/

Fractionation of mixed xylenols

2,4-XYLENOL AND M-CRESOL IN AN EMULSIFIED FORMULATION OF HYDROCARBONS AND WATER. HORTICULTURAL FORMULATION FOR ERADICATION OF CROWN GALL TUMORS. /BACTICIN/

Xylenol 100; a high purity fraction of 2,4- and 2,5- xylenol (ortho xylenols); typical composition: 2,4- 2,5-xylenol 93%; meta para cresol 2%; other xylenols 5% /From table/

Pitt-Consol Xylenol 410 is a synthetic xylenol blend ... homolog distribution, wt %: 2,6-xylenol, 1; 2,4-xylenol, 42; 2,5-xylenol, 43; 2,3-xylenol group, 14. /Xylenol 410/

Bulk Lysol Brand Disinfectant, soluble concentrate, 1.5% 2,4-xylenol.

For more Formulations/Preparations (Complete) data for 2,4-DIMETHYLPHENOL (11 total), please visit the HSDB record page.

Cosmetics product ingredient: 2,4-Dimethylphenol

Information on 6 consumer products that contain 2,4-Xylenol in the following categories is provided:

Plastics Material and Resin Manufacturing

Phenol, 2,4-dimethyl-: ACTIVE

ISOMERIZATION OF 1,4-DIMETHYLBENZENE OXIDE TO 2,4-DIMETHYLPHENOL WAS ANALOGOUS TO METHYL MIGRATION IN ENZYMIC CONVERSION OF 4-METHYLPHENYLALANINE TO 3-METHYLTYROSINE WITH PHENYLALANINE HYDROXYLASE.

Discontinued by TUCO, Division of the Upjohn Co. /Bacticin/