N-Methylaniline

Nitrogen Compounds -> Amines, Aromatic

Flammable agents - 2nd degree

Dye

Log kow = 1.66

1.7

0.989 at 68 °F (USCG, 1999) - Less dense than water; will float

0.989 @ 20 °C/4 °C

Relative density (water = 1): 0.99

0.989

0.99 @ 20°C

0.99

COLORLESS OR SLIGHTLY YELLOW LIQ

Yellow to light brown liquid.

1 to 5 mg/mL at 70.7 °F (NTP, 1992)

SOL IN ETHANOL, ETHER, CARBON TETRACHLORIDE

5624 mg/l @ 25 °C

Solubility in water: none

Insoluble

175 °F (NTP, 1992)

175 °F

175 °F CC

79.5 °C c.c.

175 °F

175 °F

385.3 °F at 760 mmHg (NTP, 1992)

196.25 °C

194-196 °C

385.3 °F

196.2 °C @760 [mm Hg]

384 °F

-71 °F (NTP, 1992)

-57 °C

-57 °C

-71 °F

-57 °C

-71 °F

Danger

H301: 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)

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

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

Chemical: Benzenamine, N-methyl-

Benzenamine, N-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, N-methyl- 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: 28-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/12653

Methylaniline: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Special Hazards of Combustion Products: Toxic vapors are generated when heated. (USCG, 1999)

· Combustible material: may burn but does not ignite readily.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 79.5 °C explosive vapour/air mixtures may be formed.

Inhalation causes dizziness and headache. Ingestion causes blush discoloration (cyanosis) of lips, ear lobes, and fingernail beds. Liquid irritates eyes. Absorption through skin produces same symptoms as for ingestion. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

Methemoglobinemia and liver injury occur in animals exposed to high concentrations over a period of weeks and months. There are no reports of human poisoning by monomethyl aniline. Listed in table of Industrial Chemicals for Which Methemoglobin Formation is the Principal Cause of Toxicity; [ACGIH] Can induce methemoglobinemia; [ICSC]

2294 153

2294 153

Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 2 ppm (9 mg/cu m). Skin Designation.

Vacated 1989 OSHA PEL TWA 0.5 ppm (2 mg/cu m), skin designation, is still enforced in some states.

N-METHYLANILINE is an aryl an amine. 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 is generated in combination with strong reducing agents, such as hydrides.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use water spray, powder, foam, carbon dioxide.

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. Give a slurry of activated charcoal in water to drink. Refer for medical attention .

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

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.

General First Aid:

(General first aid procedures)

· Wear positive pressure self-contained breathing apparatus (SCBA).

Biological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or at end of shift. [ACGIH]

0.5 [ppm]

IN GENERAL, MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMP INTO TOXIC COMPONENTS...SHOULD BE STORED IN A COOL, WELL-VENTILATED PLACE, OUT OF DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, & SHOULD BE PERIODICALLY INSPECTED... INCOMPATIBLE MATERIALS SHOULD BE ISOLATED FROM EACH OTHER.

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.

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Immediate precautionary measure

TERRESTRIAL FATE: N-Methylaniline has low adsorptivity to soil(2) and if released on soil may leach, especially in sandy soil. It may photodegrade on the soil surface(3). Some N-methylaniline may also volatilize from the soil surface. When N-methylaniline was applied to land in sludge and the sludge allowed to dry and then tilled into the soil to a depth 6 inches within 5 days, N-methylaniline degraded fairly rapidly(1). The avg concn of N-methylaniline over 3 plots in 0-6 inch cores was 511, 138, and 16 ppb, 5, 122 and 241 days after sludge application, respectively. While 82 ppb of N-methylaniline was found in 9-15 inch cores, 5 days after application, none was found at later sampling dates. While N-methylaniline biodegrades in screening studies and may therefore be expected to biodegrade in soil, it is also known to slowly react with humic material in soil(4). It is easily oxidized(5) and may react with natural oxidants in soil(SRC).

AQUATIC FATE: The Henry's Law constant is estimated to be 1.14X10-5 atm-cu m/mol(SRC), from its vapor pressure, 0.453 mm Hg(1), and water solubility, 5624 mg/L(2). Using this Henry's Law constant, its half-life in a model river and model lake is estimated to be 3.5 and 28 days, respectively(3,SRC). N-Methylaniline is sensitive to photooxidation and may photodegrade in surface water(4). It is sensitive to oxidation(5) and may be oxidized by naturally-occurring oxidants in the water body(SRC). N-Methylaniline has a low Koc(6) and BCF(7) would not be expected to adsorb to sediment or bioconcentrate in fish(SRC).

ATMOSPHERIC FATE: According to its vapor pressure, 0.453 mm Hg at 25 °C(2), N-methylaniline should exist in the atmosphere as a vapor(4). It will react with photochemically-produced hydroxyl radicals with an estimated half-life of 8.8 hr(3,SRC). It may also photolyze or oxidize while in the vapor phase or in aerosols. The rates of vapor phase photolysis are unknown. N-Methylaniline is fairly soluble in water, 5624 mg/L(1), and therefore should be scavenged by rain(SRC).

Samples of fresh vegetables containing N-methylaniline include (vegetable, concn): spinach, 3.4 ppm; red cabbage, 0.3 ppm; carrots, 0.8 ppm; celery, 0.5 ppm(1). No N-methylaniline was found in cabbage, cauliflower, kale, white beet, swede, red beet, large radish and red radish(1). Samples of pickled vegetables containing N-methylaniline include (vegetable, concn): paprika, 13.1 ppm; cucumber, 13.8 ppm; cucumber with mustard, 6.1 ppm; onion, 6.8 ppm; celery, 7 ppm(1). Tilsiter cheese and brown bread contained 37.9 and 0.7 ppm of N-methylaniline, but the chemical was not found in various forms of herring, cod roe and camembert and limburger cheese(1).

The substance can be absorbed into the body by inhalation of its vapour, by inhalation of its aerosol, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Blue lips, fingernails and skin. Cough. Dizziness. Headache. Laboured breathing. Sore throat.

MAY BE ABSORBED! Further see Inhalation.

Abdominal pain. Blue lips, fingernails and skin. Dizziness. Headache. Laboured breathing. Nausea.

lassitude (weakness, exhaustion), dizziness, headache; dyspnea (breathing difficulty), cyanosis; methemoglobinemia; pulmonary edema; liver, kidney damage

In a comprehensive survey of wastewater from 4000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, N-methylaniline was identified in discharges of the following industrial category (positive occurrences, median concn in ppb): petroleum refining (1; 161.3), printing and publishing (1; 9.8), pharmaceuticals (2; 1022), foundries (1; 2.2), aluminum (1; 6.1), organic chemicals (5; 18.5), publicly owned treatment works (2; 39.8)(1). The highest effluent concn was 1736 ppb in the pharmaceuticals industry(1). N-Methylaniline was detected in the effluent of one of three New Jersey publicly-owned treatment works (POTWs) at 13-17 ppb(2). It was detected, but not quantified, in wastewater from the Kashima petrochemical complex (includes organic chemicals factory) in Japan(3). Sludge from the Muskegon County (MI) Wastewater Treatment System contained 310 ppb of N-methylaniline which was applied to land(4).

Since the pKa of N-methylaniline is 4.848(2), N-methylaniline will be partially ionized at acidic environmental pHs and its adsorption to soil would be expected to be pH-dependent(SRC). The Koc for N-methylaniline predicted from molecular structure is 65(3). According to a suggested classification scheme(5), this estimated Koc suggests that N- methylaniline will be highly mobile in soil(SRC). Batch equilibrium studies used to determine the adsorption isotherms for N-methylaniline to a Podzol (4.85% OC pH 2.8), an Alfisol (1.25% OC, pH 6.7) and a sediment (1.58% OC, pH 7.1) yielded the results (soil, Freundlich adsorption constants (Kf), Freundlich exponent (1/n), Koc): Podzol, 22.29, 0.89, 460; Alfisol, 0.59, 0.78, 47; Sediment, 1.12, 0.77, 71(1). N-Methylaniline will be almost completely ionized at the pH of the Podzol and therefore ionic interactions may be dominant(1,SRC). N-Methylaniline reacts slowly with humates possibly by adding to quinoidal structures in the humic substances(4). Covalent bond formation is inferred by the lack of extractability of the aniline from the humic material as well as reactions with model compounds(4).

N-METHYLANILINE YIELDS ANILINE IN RABBIT; IN RAT. IT YIELDS P-METHYLAMINOPHENOL IN RABBIT. /FROM TABLE/

N-METHYLANILINE YIELDS N,N-DIMETHYLANILINE IN MYCOBACTERIUM. /FROM TABLE/

THE METABOLISM OF N-METHYLANILINE WAS STUDIED IN VITRO IN SEVERAL TISSUES OF THE IMMATURE HUMAN FETUS AND IN THE HUMAN PLACENTA. THE HIGHEST METABOLIZING ACTIVITY WAS OBSERVED IN THE LIVER. COMPARED TO ADULT RAT LIVER THE RANGE OF HEPATIC METABOLIC ACTIVITY VARIED FROM 5 TO APPROX 50% IN SOME FETUSES FOR N-METHYLANILINE DEMETHYLASE. ADRENAL GLAND HOMOGENATES HAD MEASURABLE N-METHYLANILINE METABOLIZING ACTIVITIES. IN THE GI TRACT, BRAIN, KIDNEYS, AND LUNGS THERE WAS NEGLIGIBLE OR NO ACTIVITY. IN ONE OF FIVE PLACENTAS STUDIED, ENZYME ACTIVITY COMPARABLE TO THAT IN THE LIVER WAS DETECTED. COFACTOR REQUIREMENTS OF THIS ENZYME INDICATED THAT IT WAS A DRUG-METABOLIZING MIXED-FUNCTION OXIDASE. IT WAS INHIBITED IN VITRO BY COMPOUNDS KNOWN TO BE SUBSTRATES OF LIVER MICROSOMAL DRUG METABOLIZING ENZYMES. THE LEVEL OF GLUCOSE-6-PHOSPHATE DEHYDROGENASE ACTIVITY IN THE FETAL LIVER WAS THE SAME OR HIGHER THAN IN ADULT RAT OR HUMAN LIVER.

N-Methylaniline is a known human metabolite of N,N-Dimethylaniline.

Used as a solvent and in organic synthesis; [ACGIH] Solvent for organic reactions and for nitrocellulose; [HSDB]

ORGANIC SYNTHESIS, SOLVENT, ACID ACCEPTOR

SOLVENT FOR ORGANIC REACTIONS & FOR NITROCELLULOSE

2023: <50,000 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

REACTION OF ANILINE & METHANOL IN THE PRESENCE OF A COPPER-ALUMINA CATALYST

MADE BY HEATING ANILINE CHLORIDE & METHYL ALCOHOL UNDER PRESSURE