2,4-ジメチルアニリン

log Kow = 1.68 at pH of 7.5

1.68

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

0.9723 @ 20 °C/4 °C

Relative density (water = 1): 0.97

1 to 5 mg/mL at 63 °F (NTP, 1992)

Sol in alcohol, ether, benzene; slightly soluble in water

Soluble in organic solvents.

Solubility in water, g/100ml at 20 °C: 0.5

205 °F (NTP, 1992)

90 °C

417 °F at 760 mmHg (NTP, 1992)

214 °C @ 760 mm Hg

214 °C

61 °F (NTP, 1992)

-14.3 °C

Prisms; boiling-point 255.1 °C at 760 mm Hg; melting point 235 °C; practically insoluble in cold water /2,4-xylidine hydrochloride/

-16 °C

Odor threshold in air= 1.00X10+12 molecules/cc. /Xylidine/

Threshold for xylidine is 0.0240 mg/cu m /Xylidine/

1 mmHg at 126.7 °F ; 5 mmHg at 175.6 °F; 760 mmHg at 412.7 °F (NTP, 1992)

0.13 [mmHg]

Vapor pressure: 1 mm Hg at 52.6 °C

0.133 mm Hg at 25 °C

Vapor pressure, Pa at 20 °C: 11

Danger

H301+H311+H331 (18.3%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]；H301+H311 (50%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]；H301 (99.5%): Toxic if swallowed [Danger Acute toxicity, oral]；H311 (99.5%): Toxic in contact with skin [Danger Acute toxicity, dermal]；H319 (53.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H330 (53.8%): Fatal if inhaled [Danger Acute toxicity, inhalation]；H331 (46.6%): Toxic if inhaled [Danger Acute toxicity, inhalation]；H373 (99%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]；H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P337+P317, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 208 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Chemical: Benzenamine, 2,4-dimethyl-

Status: Active Update: 06-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/2085

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

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 90 °C explosive vapour/air mixtures may be formed.

SYMPTOMS: Symptoms of exposure to this compound may include headaches, drowsiness, cyanosis, mental confusion, convulsions, nervous system and blood effects, fatigue, anorexia, loss of appetite, dizziness, and damage to the lungs, liver and kidneys.；ACUTE/CHRONIC HAZARDS: This compound may be absorbed through the skin and may cause irritation on contact. When heated to decomposition it emits toxic fumes. (NTP, 1992)

An eye and mild skin irritant; Can be absorbed through skin; Inhalation of high concentrations can cause methemoglobinemia and lowering of consciousness; Repeated or chronic exposure may have effects on the blood (anemia), liver, and kidney; High dose animal studies have produced liver necrosis, inhibition of DNA synthesis in the testes, and evidence of mutagenicity; [ICSC] A severe eye irritant in rabbits, with corneal opacity and conjunctival irritation persisting in some animals until study termination (21 days); Produced skin sensitization in 50% of guinea pigs using a modified Buehler method; [EPA TSCATS] An irritant; Toxic by ingestion, inhalation, and skin absorption; May have cumulative adverse effects to organs; [Alfa Aesar MSDS] See Xylidine, mixed isomers.

The major hazards encountered in the use and handling of 2,4-xylidine stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, and dermal absorption), exposure to this colorless liquid may occur from its use as a chemical intermediate for dyes, pesticides, and pharmaceuticals. Contact with 2,4-xylidine may cause burns to the skin and eyes. Death is also a possible outcome from exposure. While the OSHA PEL is set at a TWA of 5 ppm, the ACGIH lists xylidine (mixed isomers) on its 1988-1989 Notice of Intended Changes with a proposed TLV of 0.5 ppm, and a designation of "suspected human carcinogen". In activities or situations where over-exposure may occur, wear a self-contained breathing apparatus, and full chemical protective clothing which is specifically recommended by the shipper or manufacturer to prevent skin contact with xylidine. If contact should occur, immediatly flush the affected skin or eyes with running water for at least 15 minutes. Remove contaminated clothing and shoes at the site. Do not eat or smoke in xylidine work areas. While xylidine does not ignite easily, it can burn with the production of irritating or poisonous gases. Also, containers may explode violently in the heat of a fire. Fires involving xylidine may be extinguished with dry chemical, CO2, Halon, or standard foam. Water spray if used, should be applied with caution because it may cause frothing. Fight the fire from a maximum distance and dike runoff from fire control water. Xylidine should be stored away from heat, strong oxidizers, and hypochlorite bleaches. Shipping regulations and other DOT regulatory requirements should be consulted before transport. If xylidine should spill, dike far ahead, then take up with sand or other noncombustible absorbent and place into containers for later disposal. Incineration is a possible form of disposal for xylidine. Before implementing land disposal of waste 2,4-xylidine, consult with environmental regulatory agencies f

USEPA/ECAO. 1987. Health and Environmental Effects Profile for 2,4-Dimethylaniline and 2,4-dimethylaniline hydrochloride. ECAO-CIN-P206. (EPA-600/X-87/038)

USEPA/ECAO. 1986. Health and Environmental Effects Profile for N,N-Dimethylaniline. ECAO-CIN-P204. (EPA-600/X-87/052)

Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 5 ppm (25 mg/cu m). Skin Designation. /Xylidine/

Vacated 1989 OSHA PEL TWA 2 ppm (10 mg/cu m), skin designation, is still enforced in some states. /Xylidine/

2,4-XYLIDINE ignites on contact with fuming nitric acid (NTP, 1992). Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

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

Use water spray, carbon dioxide, foam, powder.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. 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.

Rinse mouth. 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.；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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.；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. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure 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)

Use water spray, dry chemical, foam, or CO2. Wear full protective clothing. /Xylidines/

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. /Xylidines/

Environmental considerations - land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Xylidines/

Environmental considerations - water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Xylidines/

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.；STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere, and store it at refrigerated temperatures. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)

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.

Disposal methods: incineration. A). Dissolve in such combustible solvent as alcohols, benzene, etc. Spray solvent into the furnace with afterburner and scrubber. B). Pour into a mixture of sand and soda ash (9:1). After mixing, put into a paper carton stuffed full with packing paper to serve as fuel. Burn in the furnace. /Xylidines/

Personal protection: chemical protection suit and filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

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.

Non-impervious clothing which becomes contaminated with xylidine should be removed immediately and not reworn until the xylidine is removed from the clothing. /Xylidines/

Eating and smoking should not be permitted in areas where liquid xylidine is handled, processed, or stored. /Xylidines/

Employees who handle liquid xylidine should wash their hands thoroughly with soap or mild detergent and water before eating, smoking, or using toilet facilities. /Xylidines/

For more Preventive Measures (Complete) data for 2,4-XYLIDINE (7 total), please visit the HSDB record page.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:；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 the immediate precautionary measure distance, in the downwind direction, as necessary.；FIRE: If tank, rail tank car or highway tank 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, 2024)

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 200(SRC), determined from a measured log Kow of 1.68(2) and a recommended regression-derived equation(3), indicates that 2,4-xylidine will have moderate mobility in soil(SRC). However, anilines are expected to bind strongly to humus or soil organic matter in soils due to the high reactivity of the aromatic amino group(4,5), suggesting that mobility may be much lower in some soils with high organic carbon contents(SRC). Volatilization of 2,4-xylidine may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 2.5X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(6). Based on limited data, 2,4-xylidine may biodegrade under aerobic conditions in soil(SRC); 2,4-xylidine was completely biodegraded in soil cultures within 2 days(7), and reached 36% degradation in 6 hours in an aqueous screening study using an activated sludge inoculum(8). However, it was classified as slow to biodegrade in the Japanese MITI test(9).

AQUATIC FATE: Based on a recommended classification scheme for soil(1), an estimated Koc value of 200(SRC), determined from a measured log Kow of 1.68(2) and a recommended regression-derived equation(3), suggests that 2,4-xylidine should not adsorb to suspended solids and sediment in water(SRC). However, aromatic amine groups are recognized as having a strong affinity to organic carbon, suggesting that this compound may bind strongly to suspended organic material in water(4,5). 2,4-Xylidine may volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 2.5X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(6). Estimated volatilization half-lives for a model river and model lake are 16 and 120 days, respectively(3,SRC), although adsorption to organic material may attenuate this process(SRC). According to a classification scheme(7), an estimated BCF value of 11(3,SRC), from a measured log Kow(2), suggests that bioconcentration in aquatic organisms is low(SRC). Based on limited data, 2,4-xylidine may rapidly biodegrade under aerobic conditions in water(SRC); 2,4-xylidine was completely biodegraded in soil cultures within 2 days(8) and reached 36% degradation in 6 hours in an aqueous screening study using an activated sludge inoculum(9). However, it was classified as slow to biodegrade in the Japanese MITI test(10). As a class, aromatic amines react relatively rapidly in sunlit natural water via reaction with photochemically-produced hydroxyl radicals and peroxy radicals(11); typical half-lives for peroxy and hydroxy radical reactions are on the order of 19 and 30 sunlight hours, respectively(11).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4-xylidine, which has a measured vapor pressure of 0.133 mm Hg at 25 °C(2), should exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,4-xylidine 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 about 2 hours(3,SRC).

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.；Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

Dizziness. Drowsiness. Headache. Nausea.

MAY BE ABSORBED! Redness. See Ingestion.

Redness. Pain.

Blue lips, fingernails and skin. Dizziness. Drowsiness. Headache. Nausea. Unconsciousness.

Initial medical examination: a complete history & physical examination. The purpose is to detect existing conditions that might place the exposed employee at increased risk, and to establish a baseline for future health monitoring. Exam of the blood, lungs, liver, kidneys, and cardiovascular system should be stressed. ... Periodic medical exam ... should be repeated on an annual basis. /Xylidine/

The Koc of 2,4-xylidine is estimated as approximately 200(SRC), using a measured log Kow of 1.68(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that 2,4-xylidine has moderate mobility in soil(SRC). However, adsorption to soil due to the high reactivity of the aromatic amino group to humus or soil organic matter rather than to clay particles may cause decreased mobility of this compound(4,5). Low adsorption is observed at a neutral pH with pure clay minerals or soils for substituted anilines(5).

2,4-Xylidine, incubated in chernozem soil at 500 ppm/kg, was biodegraded within 2 days; its transformation product was stable for >90 days(1). 2,4-Xylidine, initially present at 20 mg/l, was degraded by 36% in 6 hours using an activated sludge inoculum under aerobic conditions(2). In the Japanese MITI test, 2,4-xylidine (present at 100 mg/l) was classified as slow to biodegrade indicating that only 0-29% of the theoretical BOD was reached in 2 weeks using an activated sludge inoculum(3).

2,4-Xylidine

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 16: (1978) Some Aromatic Amines and Related Nitro Compounds – Hair Dyes, Colouring Agents and Miscellaneous Industrial Chemicals；Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)

1987

1987

An estimated BCF value of 11 was calculated for 2,4-xylidine(SRC), using a measured log Kow of 1.68(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).

Chemical: Benzenamine, 2,4-dimethyl-

Status: Active Update: 06-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/2085

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

YIELDS IN RABBITS 4-AMINO-3-METHYLBENZOIC ACID & 2,4-DIMETHYLPHENYLSULFAMATE. /FROM TABLE/

2,4-Xylidine is oxidized mainly to 3-methyl-4-aminobenzoic acid.

2,4-Xylidine is absorbed through the GI tract, the skin and the respiratory tract. It is metabolized and excreted in the urine. In the urine of rats, 2,4-xylidine appears mainly unchanged or as 4-amino-3-methylbenzoic acid or N-acetyl-4-amino-3-methylbenzoic acid and their sulfate or glucuronide conjugates. These compounds are formed after oxidation at the p- methyl group. In addition, 6-hydroxy-2,4-xylidine has been identified as a major metabolite in the urine or dogs. Traces of N-methyl-2,4-dimethyl-aniline are also detectable in the urine of both species. The quantity of metabolites in the urine does not incr after repeated admin of 2,4-xylidine.

The xylidine 2,4-dimethylaniline produces hepatic cholangiofibrosis, bile duct proliferation, and foci of cellular hyperplasia and degeneration in the rat. The same cmpd is relatively innocuous in the dog. ... The major urinary metabolite of 2,4-dimethylaniline in the rat was N-acetyl-4-amino-3-methylbenzoic acid while in the dog it was 6-hydroxy-2,4-dimethylaniline. The dog also produced a smaller amt of unacetylated 4-amino-3-methylbenzoic acid and its glycine conjugate. ... In rats, repeated admin of either xylidine /2,4-dimethylaniline or 2,6-dimethylaniline/ for 10 days failed to incr the appearance of metabolites, but 3-methylcholanthrene did incr the urinary concn of N-acetyl-4-amino-3-methylbenzoic acid in 2,4-dimethylaniline dose rats.

2,4-dimethylaniline has known human metabolites that include N-(2,4-Dimethylphenyl)acetamide.

Used to make pharmaceuticals, pesticides, dyes, and photographic chemicals; [HSDB] Also used to make wood preservatives, wetting agents for textiles, frothing agents for ore dressing, metal complexes, and special lacquers; [EPA PPRTV]

Pesticide and pharmaceutical intermediate

Used as a chemical intermediate for the synthesis of acetoacet-2,4-xylidide; Acid Orange 24; Acid Red 26; amitraz; 3-hydroxy-2-naphth-2'l,4'-xylidide; mefluidide; Solvent Orange 7.

Chemical intermediate for Direct Violet 14.

Used as an intermediate for photographic chemicals, pesticides, and dyes.

Substance listed with specific concentration in tattoo ink and/or permanent make up according to EU Commission Regulation 2020/2081. The concentration limit (by weight) is 0.0005%.

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

... By reduction of asymmetrical 2,4-dimethylnitrobenzene with iron & acetic acid. ... Commercially by nitrating & reducing commercial xylene & is separated from resulting isomeric mixt of xylidines by formation of the acetate salt.

m-Xylene (nitration/nitro reduction; coproduced with 2,6-xylidine)

... Usually obtained by iron reduction of the corresponding nitroxylene.

Produced by the catalytic hydrogenation of the corresponding nitro derivative.