2,3-Xylidin

0.9931 at 68 °F (NTP, 1992) - Less dense than water; will float

0.9931 @ 20 °C

Relative density (water = 1): 0.99

1 to 5 mg/mL at 75 °F (NTP, 1992)

Sol in alcohol, ether; soluble in carbon tetrachloride

Slightly sol in water

Soluble in oxygenated solvents.

Solubility in water, g/100ml at 20 °C: 15

206 °F (NTP, 1992)

206 °F (97 °C) (Closed cup)

96 °C c.c.

430 to 432 °F at 760 mmHg (NTP, 1992)

221.5 °C @ 760 mm Hg

222 °C

less than 5 °F (NTP, 1992)

< -15 °C

2 °C

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

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

7.5X10-2 mm Hg at 25 °C

Vapor pressure, Pa at 25 °C: 13

Danger

H301+H311+H331 (49.8%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

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 209 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

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

Chemical: Benzenamine, 2,3-dimethyl-

Status: Active Update: 07-06-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/11559

2,3-Dimethylaniline: Does not have an individual approval but may be used under an appropriate group standard

This compound is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 96 °C explosive vapour/air mixtures may be formed.

The major hazards encountered in the use and handling of 2,3-xylidine stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, and dermal absorption), exposure to this liquid may occur from its use as a chemical intermediate for dyes. Contact with 2,3-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 2,3-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/

2,3-XYLIDINE reacts with strong oxidizing agents and hypochlorite bleaches (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 compound can be controlled using 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 dry chemical, foam, carbon dioxide, or water spray. Water may be ineffective. Water or foam may cause frothing. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products.

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 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 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 2,3-XYLIDINE (7 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 120(SRC), determined from a structure estimation method(2), indicates that 2,3-xylidine will have high 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(3,4), suggesting that mobility may be much lower in some soils(SRC). Volatilization of 2,3-xylidine may occur 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(5). Based on limited screening study data, 2,3-xylidine may be readily biodegraded in soil(SRC); 2,3-Xylidine, reached 96.5% degradation (measured as removal of COD) with a rate of biodegradation of 12.7 mg COD/g-hr using an activated sludge inoculum(6).

AQUATIC FATE: Based on a recommended classification scheme for soil(1), an estimated Koc value of 120(SRC), determined from a structure estimation method(2), indicates that 2,3-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). 2,3-Xylidine may volatilize from water surfaces(5,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 half-lives for a model river and model lake are 16 and 120 days, respectively(5,SRC), although adsorption to organic material may attenuate this process(SRC). According to a classification scheme(7), an estimated BCF value of 26(5,SRC), from an estimated log Kow(8,SRC), suggests that bioconcentration in aquatic organisms is low(SRC). Based on limited aqueous screening study data, 2,3-xylidine may be readily biodegraded in water(SRC); 2,3-Xylidine, reached 96.5% degradation (measured as removal of COD) with a rate of biodegradation of 12.7 mg COD/g-hr using an activated sludge inoculum(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,3-xylidine, which has a measured vapor pressure of 0.0.075 mm Hg at 25 °C(2), should exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,3-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.

Dimethylanilines, unspecified isomers, were detected in coal-derived liquids, mainly from liquification and hydrocarbonization processes(1). 2,3-Xylidine was identified at unreported concentrations in Latakia tobacco smoke and a steam distillate of Latakia tobacco(2).

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/

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2,3-xylidine can be estimated to be about 120(SRC). According to a recommended classification scheme(2), this estimated Koc value suggests that 2,3-xylidine has high 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(3,4). Low adsorption is observed at a neutral pH with pure clay minerals or soils for substituted anilines(4).

An estimated BCF value of 26 was calculated for 2,3-xylidine(SRC), using an estimated log Kow of 2.2(1,SRC) 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 Henry's Law constant for 2,3-xylidine is estimated as 2.5X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that 2,3-xylidine will volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the 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 hours(2,SRC). The 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), although adsorption to organic material in water may attenuate this process(SRC). 2,3-Xylidine's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces may occur(SRC).

2,3-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/

All isomers were individually tested for their potential of producing methemoglobinemia. A single intravenous injection of 0.25 mM/kg bw of the isomers produced methemoglobin levels in the blood of cats from 6.3% to 38.3%. /Xylidine (Mixed Isomers)/

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.

The oral application of 200 mg/kg bw or the intraperitoneal injection of 100 mg/kg bw inhibited testicular DNA synthesis in male mice by the 2,4-, 2,5-, and 3,4-isomers. No inhibition was found by the 2,3-, 2,6-, and 3,5-xylidines.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Xylidine is produced, as an intermediate or final product, by process units covered under this subpart. /Xylidine/

CHEMICAL INTERMEDIATE FOR DYES

Used as a chemical intermediate for the synthesis of mefenamic acid.

NITRATION AND REDUCTION OF COMMERCIAL XYLENE, FOLLOWED BY REMOVAL OF THE 2,4-, 2,5-, AND 2,6-ISOMERS, RESIDUE IS MADE ALKALINE AFTER WHICH 2,3-ISOMER IS PRECIPITATED AS FORMYL DERIV

o-Xylene (nitration/nitro reduction; byproduct of 3,4-xylidine production)