ChemicalBook > Product Catalog > Organic Chemistry > Amides > Naphthenic amines derivatives > N-Methylaniline
N-Methylaniline Chemical Properties
- Melting point:−57 °C(lit.)
- Boiling point:196 °C(lit.)
- Density 0.989 g/mL at 25 °C(lit.)
- vapor pressure 0.5 hPa (20 °C)
- refractive index n
- Flash point:174 °F
- storage temp. Store below +30°C.
- solubility water: slightly soluble30g/L
- form Liquid
- pka4.84(at 25℃)
- color Clear yellow to brown
- OdorModerate aniline-type.
- PH7.6 (1g/l, H2O, 20℃)
- Water Solubility 30 g/L
- Sensitive Air Sensitive
- Merck 14,6019
- BRN 741982
- Henry's Law Constant(x 10-5 atm?m3/mol): 1.19 at 25 °C (approximate - calculated from water solubility and vapor pressure)
- Exposure limitsNIOSH REL: TWA 0.5 ppm (2 mg/m3), IDLH 100 ppm; OSHA PEL: TWA 2 ppm (9 mg/m3); ACGIH TLV: TWA 0.5 ppm (adopted).
- Stability:Stability Combustible. Incompatible with strong oxidizing agents. Discolours upon exposure to air.
- CAS DataBase Reference100-61-8(CAS DataBase Reference)
- NIST Chemistry ReferenceAniline, N-methyl-(100-61-8)
- EPA Substance Registry SystemN-Methylaniline (100-61-8)
- Hazard Codes T,N
- Risk Statements 23/24/25-33-50/53
- Safety Statements 28-36/37-45-60-61-28A
- RIDADR UN 2294 6.1/PG 3
- WGK Germany 3
- RTECS BY4550000
- F 8
- Autoignition Temperature500 °C
- TSCA Yes
- HazardClass 6.1
- PackingGroup III
- HS Code 29214200
- Hazardous Substances Data100-61-8(Hazardous Substances Data)
- ToxicityLD in rabbits (g/kg): 0.28 orally; in rabbits, cats (mg/kg): 24, 24 i.v. (Treon)
N-Methylaniline Usage And Synthesis
- Chemical PropertiesN-Methylaniline is a yellow to light brown oily liquid with a weak, ammonia-like odor. Turns reddishbrown if left standing. The odor threshold is 1.7 ppm
- Physical propertiesColorless to yellow to pale brown liquid with a faint, ammonia-like odor. Odor threshold concentration is 1.7 ppm (quoted, Amoore and Hautala, 1983).
- UsesN-Methylaniline is used as a solvent and in organic synthesis.
- UsesChemical syntheses
- UsesOrganic synthesis, solvent, acid acceptor.
- DefinitionChEBI: A methylaniline that is aniline carrying a methyl substituent at the nitrogen atom.
- Synthesis Reference(s)Chemical and Pharmaceutical Bulletin, 14, p. 1007, 1966 DOI: 10.1248/cpb.14.1007
Journal of the American Chemical Society, 107, p. 493, 1985 DOI: 10.1021/ja00288a037
Synthetic Communications, 13, p. 601, 1983 DOI: 10.1080/00397918308059535
- HazardToxic by ingestion, inhalation, and skin absorption. Methemoglobinemia and central nervous system impairment.
- Health HazardRecommended Personal Protective Equipment: Approved respirator; rubber gloves; splash proof goggles; Symptoms Following Exposure: Inhalation causes dizziness and headache. Ingestion causes bluish discoloration (cyanosis) of lips, ear lobes, and fingernail beds. Liquid irritates eyes. Absorption through skin produces same symptoms as for ingestion; General Treatment for Exposure: INHALATION: remove victim to fresh air and call a physician at once; administer oxygen until physician arrives. INGESTION: give large amount of water; get medical attention at once. EYES or SKIN: flush with plenty of water for at least 15 min.; if cyanosis is present, shower with soap and warm water, with special attention to scalp and finger nails; remove any contaminated clothing; Toxicity by Inhalation (Threshold Limit Value): Data not available; Short-Term Inhalation Limits: Data not available; Toxicity by Ingestion: Data not available; Late Toxicity: Data not available; Vapor (Gas) Irritant Characteristics: Data not available; Liquid or Solid Irritant Characteristics: Data not available; Odor Threshold: Data not available.
- Chemical ReactivityReactivity with Water No reaction; Reactivity with Common Materials: May attack some forms of plastic; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
- Safety ProfilePoison by ingestion and intravenous routes. Moderately toxic by subcutaneous route. When heated to decomposition it emits toxic fumes of NOx.
- Potential ExposureThe material is used as an intermediate in organic synthesis, as a solvent and as an acid acceptor
- CarcinogenicityN-methyl aniline (1.95 g/kg of food) given
together with sodium nitrite (1.0 g/l of drinking
water) to Swiss mice resulted in a 17% incidence
of lung adenomas and a 14% incidence
of malignant lymphomas; there were no carcinogenic
effects in animals treated with Nmethyl
aniline alone, suggesting that in vivo
nitrosation is necessary for forming carcinogenic
In bacterial mutagenicity assays N-methyl aniline was negative with or without metabolic activation.
- Environmental FateSoil. Reacts slowly with humic acids or humates forming quinoidal structures (Parris, 1980).
- ShippingUN2294 N-Methylaniline, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
- Purification MethodsDry it with KOH pellets and fractionally distil it under vacuum. Acetylate, and the acetyl derivative is recrystallised to constant melting point (m 101-102o), then hydrolysed with aqueous HCl and distilled from zinc dust under reduced pressure. [Hammond & Parks J Am Chem Soc 77 340 1955, Beilstein 12 IV 241.]
- Waste DisposalControlled incineration whereby oxides of nitrogen are removed from the effluent gas by scrubber, catalytic or thermal device.
N-Methylaniline Preparation Products And Raw materials
- Raw materialsMethanolDimethyl sulfatePhosphorus trichlorideAnilineWaterN,N-DimethylanilineDimethyl ether
- Preparation ProductsVanillin2,6-Dimethylaniline5-AzaindoleCrystal VioletBuprofezin4-Dimethylaminobenzaldehyde1H-PYRROLO[2,3-B]PYRIDINE, 2-METHYL-4,4'-Bis(dimethylamino)benzophenoneBenzothiazoleREACTIVE BLUE 42-Amino-4,6-dimethoxypyrimidineBasic Blue 54o-AcetoacetanisideHexamethyldisiloxaneMefenacetN-METHYL-N-PHENYL-2-PIPERAZIN-1-YLACETAMIDEMethyl OrangeN-2,4-DIMETHYLPHENYL-N'-METHYLFORMAMIDINEMethylene BluePigment Green 18FluorocytosineXylocaine4-(TRIMETHYL-UREIDO)-BENZENESULFONYL CHLORIDEASTRAZON PINK FGN-(2-Hydroxyethyl)-N-methylanilineN-METHYL-N-PHENYLCARBAMOYL CHLORIDEAcid Yellow 1274-(Dimethylamino)benzophenone1-Methyl-1-phenylhydrazineASTRAZON BRILLIANT RED 4GRIBITYL-3,4-XYLIDINE*2-Chloro-N-(2,6-dimethylphenyl)acetamideN-Chloromethyl-N-phenylaminoformyl chloride4-(DIMETHYLAMINO)PHENYL THIOCYANATEN-METHYL-N-BENZYLANILINE1,2-DIPHENYLVINYLENE CARBONATE
- N-(2-Hydroxyethyl)-N-methylaniline N-(2-HYDROXYETHYL)-N-METHYL-4-TOLUIDINE 4-Nitro-N-methylphthalimide 3-CHLORODIPHENYLAMINE 4-CHLOROBENZANILIDE 4'-Bromoacetanilide 2-DIMETHYLAMINO-9-FLUORENONE 2-acetamido-3-nitro-9-fluorenone 4-Bromo-N,N-dimethylaniline Diphenylcarbamyl chloride 2'-Fluoroacetanilide 2-DIMETHYLAMINO-3-NITROFLUORENE 4-Chloro-N-methylaniline 3-(TRIFLUOROMETHYL)ACETANILIDE 2-(dimethylamino)fluorene 2-Chloro-N-[4-chloro-2-(2-chlorobenzoyl)phenyl]acetamide 2-ACETAMIDOFLUORENE N-Chloroethyl-N-ethylaniline
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- Sep 23，2019