3,4-Xylidin

log Kow= 1.84

1.84

1.86

1.076 at 64 °F (NTP, 1992) - Denser than water; will sink

1.076 @ 18 °C

Relative density (water = 1): 1.07

Plates of prisms from petroleum ether

Crystalline solid

less than 1 mg/mL at 66 °F (NTP, 1992)

Sol in ether, petroleum

Very soluble in ligroin; soluble in ether; slightly soluble in chloroform and water.

Soluble in aromatic solvents.

Solubility in water, g/100ml at 22 °C: 0.38

209 °F (NTP, 1992)

98 °C

442 °F at 760 mmHg (NTP, 1992)

228 °C @ 760 MM HG

228 °C

124 °F (NTP, 1992)

51 °C

51 °C

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

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

Danger

H301 (96.3%): Toxic if swallowed [Danger Acute toxicity, oral]

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

Aggregated GHS information provided per 54 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

Chemical: Benzenamine, 3,4-dimethyl-

Status: Cease Manufacture Update: 11-05-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/10998

3,4-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 98 °C explosive vapour/air mixtures may be formed.

SYMPTOMS: Symptoms of exposure to this compound may include headaches, drowsiness, cyanosis, mental confusion, convulsions, anorexia, nervous system and blood effects, fatigue, loss of appetite, dizziness, and damage to the lungs, liver and kidneys.

The major hazards encountered in the use and handling of 3,4-xylidine stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, and dermal absorption), exposure to this crystalline material may occur from its use as a chemical intermediate for the synthesis of riboflavin (vitamin B2). Contact with 3,4-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, immediately 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 3,4-xylidine should spill, carefully shovel the material into clean covered containers (solutions are first diked far ahead, then taken up with sand or other noncombustible absorbent) for later disposal. Incineration is a possible form of disposal for xylidine. Before implementing land disposal of waste 3,4-xylidine, consult with environmental regulatory agencies for guidance.

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/

3,4-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.

Decomposes on burning. This produces toxic and corrosive fumes including nitrogen oxides. Reacts violently with strong oxidants. Reacts with hypochlorites. This produces explosive chloroamines. Reacts with acids, acid anhydrides, acid chlorides and halogens. Attacks plastic and rubber.

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 .

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

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.

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: 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.

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 particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers.

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 3,4-XYLIDINE (7 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 240(SRC), determined from a measured log Kow of 1.84(2) and a recommended regression-derived equation(3), indicates that 3,4-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(SRC). Volatilization of 3,4-xylidine may be important from moist soil surfaces(SRC) given a measured Henry's Law constant of 1.85X10-5 atm-cu m/mole(2). Based on limited aqueous screening study data, 3,4-xylidine may biodegrade under aerobic conditions in soil(SRC); 3,4-xylidine, present at 30 mg/l, reached 7.1% of the theoretical BOD in 4 weeks using an activated sludge inoculum(6).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 240(SRC), determined from a measured log Kow of 1.84(2) and a recommended regression-derived equation(1), indicates that 3,4-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(3,4). 3,4-Xylidine may volatilize from water surfaces(1,SRC) based on a measured Henry's Law constant of 1.85X10-5 atm-cu m/mole(2). Estimated volatilization half-lives for a model river and model lake are 2 and 21 days, respectively(1,SRC). According to a classification scheme(5), measured BCF values of 1.9-3.3 and <10(6), measured in carp, suggest that bioconcentration in aquatic organisms is low(SRC). Based on limited aqueous screening study data, 3,4-xylidine may biodegrade slowly under aerobic conditions in water(SRC); 3,4-xylidine, present at 30 mg/l, reached 7.1% of the theoretical BOD in 4 weeks using an activated sludge inoculum(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3,4-xylidine, which has a measured vapor pressure of 0.028 mm Hg at 25 °C(2), should exist solely as a vapor in the ambient atmosphere. Vapor-phase 3,4-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).

Dizziness. Drowsiness. Headache. Nausea.

MAY BE ABSORBED! See Ingestion.

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, lung, liver, kidneys, and cardiovascular system should be stressed. ... Periodic medical exam ... should be repeated on an annual basis. /Xylidines/

The Koc of 3,4-xylidine is estimated as approximately 240(SRC), using a measured log Kow of 1.84(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that 3,4-xylidine has moderate mobility in soil(SRC). However, anilines are expected to bind stongly to humus or soil organic matter in soils due to the high reactivity of the aromatic amino group(4,5). Low adsorption is observed at a neutral pH with pure clay minerals or soils for substituted anilines(5).

3,4-Xylidine, present at 30 mg/l, reached 7.1% of the theoretical BOD in 4 weeks using an activated sludge inoculum(1). In the Japanese MITI test, 3,4-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(2). 3,4-Xylidine, present initially at 252 mg/L, was removed at a biodegradation rate of 30 mg COD/g-hr by an activated sludge inoculum(3). E.coli converted 3,4-xylidine to the corresponding (phenylazo)naphthol in the presence of nitrate with this reaction proceeding within 24 hours(4).

BCF values of 1.9-3.3 and <10 were measured in carp for 3,4-xylidine at 1 and 0.1 mg/l, respectively, using a flow through system(1). According to a classification scheme(3), these BCF values suggest that bioconcentration in aquatic organisms is low(SRC).

A Henry's Law constant of 1.85X10-5 atm-cu m/mole was measured for 3,4-xylidine(1). This value indicates that 3,4-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 2 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 21 days(2,SRC) although adsorption to organic material in water may attenuate this process(SRC). 3,4-Xylidine's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces may occur(SRC).

... 3,4-DIMETHYLANILINE ... CARCINOGENIC, BECAUSE ... /IT/ INDUCED PITUITARY ADENOMAS IN BUFFALO RATS.

3,4-DIMETHYLANILINE WAS TESTED FOR ITS ABILITY TO MUTATE SALMONELLA TYPHIMURIUM & WAS FOUND TO BE WEAKLY MUTAGENIC (LESS THAN 150 REVERTANTS/UMOLE).

THE ORAL LD50 VALUES IN RATS FOR DI-SUBSTITUTED ANILINES INCR COMPARED TO MONO-SUBSTITUTED ANILINES. /SUBSTITUTED ANILINES/

In the Rec-assay using Bacillus subtillis, the 2,3-, 2,5-, 2,6-, 3,4-, and 3,5-isomers were negative; 2,4-xylidine was positive.

For more Non-Human Toxicity Excerpts (Complete) data for 3,4-XYLIDINE (6 total), please visit the HSDB record page.

(1974) 4.99X10+4 GRAMS (PRINCPL CUSTMS DISTS)

(1975) 4.99X10+4 GRAMS (PRINCPL CUSTMS DISTS)

NITRATION OF O-XYLENE FOLLOWED BY REDUCTION; BROMINATION OF O-XYLENE FOLLOWED BY REACTION WITH AMMONIA

o-Xylene (nitration/nitro reduction)

Soboley and Berezooskii patented the production of 3,4-xylidine by the hydrogenation of 2-chloromethyl-4-nitrotoluene.