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Home > Encyclopedia > 2,4-Dimethylaniline

2,4-Dimethylaniline

2,4-Dimethylaniline structure

2,4-Dimethylaniline 

structure
  • CAS No:

    95-68-1

  • Formula:

    C8H11N

  • Chemical Name:

    2,4-Dimethylaniline

  • Synonyms:

    Benzenamine,2,4-dimethyl-;2,4-Xylidine;2,4-Dimethylbenzenamine;2,4-Dimethylaniline;1-Amino-2,4-dimethylbenzene;4-Amino-1,3-dimethylbenzene;4-Amino-1,3-xylene;m-Xylidine;2,4-Dimethylphenylamine;2,4-Xylylamine;NSC 7640

  • Categories:

    Organic Chemistry  >  Amides

Description

colourless to yellow or dark brown liquid


2,4-xylidine is a dark brown liquid. (NTP, 1992)|Liquid|CLEAR PALE YELLOW LIQUID WITH CHARACTERISTIC ODOUR. TURNS REDDISH TO BROWN ON EXPOSURE TO AIR.


2,4-xylidine is a dark brown liquid. (NTP, 1992)|2,4-dimethylaniline is a primary arylamine that is aniline in which the hydrogens at the 2- and 4-positions are replaced by methyl groups. A clear to yellow liquid, it is used in production of certain dyes, pesticides and other chemicals. It is a primary arylamine and a dimethylaniline.

2,4-Dimethylaniline Basic Attributes

121.18000

121.18

202-440-0

367R1L22C9

1562

7640

1711

DTXSID8026305

Colorless to tan, oily liquid

2921419000

Characteristics

26.02000

2.46680

2,4-xylidine is a dark brown liquid. (NTP, 1992)

0.9723 g/cm3 @ Temp: 20 °C

-14.3 °C

214 °C @ Press: 760 Torr

90ºC

1.558-1.56

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

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

0.16 mm Hg ( 25 °C)

4.2 (vs air)

vol% in air: 1.1.0

pKa= 4.89 at 25 °C (conjugate acid)

Forms more or less sol salts with the strong mineral acids /Xylidine/|All /isomers/ except ortho-4-Xylidine are liquids above 20 °C /Xylidine/

This chemical may be sensitive to prolonged exposure to air. Slightly soluble in water.

Amines, Aromatic

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.

520 °C

14.26 kcal/mol at 25 °C

Safety Information

II

6.1

UN 1711

2

R23/24/25; R33; R51/53

S28-S36/37-S45-S61

ZE8925000

T; N

Separated from strong oxidants, acids, acid anhydrides, acid chlorides, hypochlorites, halogens and food and feedstuffs. Well closed. Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access.

Stable. Combustible. Incompatible with strong oxidizing agents, acids, acid anhydrides, acid chlorides, chloroformates, halogens.

Missing Phrase - N15.00950417-P260-P280-P302 + P352 + P312-P304 + P340 + P312-P403 + P233

H301 + H311 + H331-H373-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.|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/

Strong oxidizers, hypochlorite bleaches /Xylidines/

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)

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.

|Danger|H301 (99.22%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P273, P280, P284, P301+P310, P302+P352, P304+P340, P305+P351+P338, P310, P311, P312, P314, P320, P321, P322, P330, P337+P313, P361, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 128 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P321, P322, P330, P332+P313, P362, P363, P403+P233, P405, and P501|H227: Combustible liquid [Warning Flammable liquids]|P210, P260, P261, P264, P270, P271, P280, P301+P312, P304+P312, P304+P340, P305+P351+P338, P307+P311, P312, P314, P321, P330, P337+P313, P370+P378, P403+P235, P405, and P501

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: 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)

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)|The following types of respirators should be selected under the prescribed concentrations: 20 ppm: Any chemical cartridge respirator with organic vapor cartridge(s); any supplied air respirator; any self contained breathing apparatus. 50 ppm: Any supplied air respirator operated in a continuous flow mode; any powdered air purifying respirator with organic vapor cartridge(s). 100 ppm: Any chemical cartridge respirator with a full facepiece and organic vapor cartridge(s); any powered air purifying respirator with a tight fitting facepiece and organic vapor cartridge(s); any air purifying full facepiece respirator (gas mask) with a chin style or front or back mounted organic vapor canister; any supplied air respirator with a full facepiece; any self contained breathing apparatus with a full facepiece. 150 ppm: Any supplied air respirator with a half mask and operated in a pressure demand or other positive pressure mode. Emergency or planned entry in unknown concentration or IDLH condition: Any self contained breathing apparatus with a full facepiece and operated in a pressure demand or other positive pressure mode; Any supplied air respirator with a full facepiece and operated in a pressure demand or other positive pressure mode in combination with an auxiliary self contained breathing apparatus operated in pressure demand or other positive pressure mode. Escape: Any air purifying full facepiece respirator (gas mask) with a chin style or front or back mounted organic vapor canister; any appropriate escape type self contained breathing apparatus. /Xylidines/|Employees should be provided with and required to use impervious clothing, gloves, face shields (eight-inch minimum), and other appropriate protective clothing necessary to prevent any possibility of skin contact with liquid xylidine. /Xylidines/|Employees should be provided with and required to use splash proof safety goggles where there is any possibility of liquid xylidine contacting the eyes. /Xylidines/

Forms explosive chloroamines on exposure to hypochlorites. /Xylidines/|Lower explosive limit in air: 1.5% by vol /Xylidines/|Explosive limits , vol% in air: 1.1-7.0

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/

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.

/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. /Xylidines; Xylidines, liquid; Xylidines, 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. /Xylidines; Xylidines, liquid; Xylidines, 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. /Xylidines; Xylidines, liquid; Xylidines, 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. /Xylidines; Xylidines, liquid; Xylidines, solid/|For more DOT Emergency Guidelines (Complete) data for 2,4-XYLIDINE (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.

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/

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.

Separated from strong oxidants, acids, acid anhydrides, acid chlorides, hypochlorites, halogens and food and feedstuffs. Well closed. Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access.

A harmful contamination of the air will be reached slowly on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.

The substance is irritating to the eyes. The substance is mildly irritating to the skin. Exposure at high levels could cause lowering of consciousness. Exposure at high levels could cause formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.

The substance may have effects on the blood. This may result in anaemia. The substance may have effects on the kidneys and liver.

NO open flames. Above 90 °C use a closed system and ventilation.

STRICT HYGIENE!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or eye protection in combination with breathing protection.

| 3 - Materials that, under emergency conditions, can cause serious or permanent injury.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

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 for guidance.

2,4-Xylidine was reported as a contaminant in water from energy technology activities(1). Dimethylanilines, unspecified isomers, was detected in coal-derived liquids, mainly from liquification and hydrocarbonization processes(2).

Toxicity

LD50 Rat male single oral 470 (320-690) mg/kg.

2,4-Xylidine's production and use as an intermediate for photographic chemicals, pesticides, and dyes(1) may result in its release to the environment through various waste streams(SRC).

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).

The rate constant for the vapor-phase reaction of 2,4-xylidine with photochemically-produced hydroxyl radicals has been estimated as 1.6X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Xylidines absorb light in the environmental spectra(2), suggesting the potential for direct photolysis in the environment(SRC). As a class, aromatic amines react relatively rapidly in sunlit natural water via reaction with photochemically-produced hydroxyl radicals and peroxy radicals(3); typical half-lives for peroxy and hydroxy radical reactions are on the order of 19 and 30 sunlight hours, respectively(3).

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).

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).

The Henry's Law constant for 2,4-xylidine is estimated as 2.5X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that 2,4-xylidine will volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the estimated volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 16 days(2,SRC). The estimated volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 120 days(2,SRC). Adsorption to organic material may attenuate this process(SRC). 2,4-Xylidine's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces may occur(SRC).

DRINKING WATER: Dimethylaniline, unspecified isomer, was detected in drinking water at an unreported location and concentration(1).|SURFACE WATER: Four of sixteen Rhine River water samples, collected at Lobith, Werkendam, and Maassiuis, The Netherlands, in 1989, contained 2,4-xylidine at concentrations ranging from 0.021 to 0.066 ug/l(1).

Occupational exposure may be through inhalation and dermal contact with this compound at workplaces where 2,4-xylidine is produced or used. The general population may be exposed to 2,4-xylidine via the ingestion of contaminated water. (SRC)

Drug Information

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.

HALF-LIFE OF 2,4-XYLIDINE ABSORPTION BY SMALL INTESTINE IN VIVO IN RAT WAS 15.7 MIN.

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)

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)


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.

2,4-dimethylaniline

The substance can be absorbed into the body in hazardous amounts by inhalation, through the skin and by ingestion.

Dizziness. Drowsiness. Headache. Nausea.


MAY BE ABSORBED! Redness. See Ingestion.


Redness. Pain.

2,4-Dimethylaniline Use and Manufacturing

Methods of Manufacturing

... 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.

Uses

2,4-Xylidine is an organic compound with formula (CH3)2C6H3NH2. It is an aromatic amine, i.e. an aniline. It is prepared by nitration of m-xylene followed by hydrogenation. Commercially significant derivatives include the veterinary drug cymiazole and the colorant Pigment Yellow 81.It is an isomer of 2,6-xylidine and 3,4-xylidine.


Intermediates


Paints and coatings

Production

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

An impure form, containing 20% of the 2,6-isomer, is used for some applications.

All other basic organic chemical manufacturing|Benzenamine, 2,4-dimethyl-: ACTIVE

THIN-LAYER CHROMATOGRAPHY HAS BEEN USED TO SEPARATE & IDENTIFY ... 2,4-XYLIDINE ... . ... 2,4-XYLIDINE, IN AIR ... ADSORBED ON SILICA GEL, DESORBED WITH ETHANOL & DETERMINED BY GAS CHROMATOGRAPHY.|... 2,4-XYLIDINE ... DETERMINED COLORIMETRICALLY BY REACTION WITH POTASSIUM PEROXYDISULFATE; IN NATURAL WATERS @ CONC OF 0.1 MG/L BY FORMING COLORED 4-AMINO-ANTIPYRINE COMPLEX.|ANALYTE: XYLIDINE; MATRIX: AIR; RANGE: 12.5-50.0 MG/CU M; PROCEDURE: ADSORPTION ON SILICA GEL, DESORPTION WITH 95% ETHANOL, GAS CHROMATOGRAPHY /TOTAL XYLIDINE/|ANALYTE: AROMATIC AMINES; MATRIX: AIR; RANGE: 0.01-14 MG/SAMPLE; PROCEDURE: ADSORPTION ON SILICA GEL; ELUTION BY ETHANOL; GAS CHROMATOGRAPHY ANALYSIS. /AROMATIC AMINES/|GAS CHROMATOGRAPHIC METHOD FOR THE ANALYSIS & SEPARATION OF ISOMERS OF XYLIDINE. /TOTAL XYLIDINE/

Computed Properties

Molecular Weight:121.18
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:121.089149355
Monoisotopic Mass:121.089149355
Topological Polar Surface Area:26
Heavy Atom Count:9
Complexity:90.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Downstream Products

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