N-methylaminobenzene

N-methylaminobenzene - Names and Identifiers

Name	Monomethylaniline
Synonyms	methyl aniline anilinomethane N-METHYLANILINE N-Methylaniline 2-methylaniline MONOMETHYLANILINE N-dimethylaniline Monomethylaniline methylphenylamine N-MONOMETHYLANILINE Methylaniline,mixed N-phenylmethylamine N-Monomethylaniline N-Methylbenzeneamine N-METHYLAMINOBENZENE (Methylamino)benzene N-Methyl-phenylamine N-methylaminobenzene (methylamino) benzene Benzenamine, N-methyl- Benzenenamine, N-methyl- methylaniline(non-specificname) Methylaniline(non-specificname)
CAS	100-61-8
EINECS	202-870-9
InChI	InChI=1/C7H9N/c1-6-4-2-3-5-7(6)8/h2-5H,8H2,1H3
InChIKey	AFBPFSWMIHJQDM-UHFFFAOYSA-N

N-methylaminobenzene - Physico-chemical Properties

Molecular Formula	C7H9N
Molar Mass	107.15
Density	0.989 g/mL at 25 °C (lit.)
Melting Point	-57 °C (lit.)
Boling Point	196 °C (lit.)
Flash Point	174°F
Water Solubility	30 g/L
Solubility	water: slightly soluble30g/L
Vapor Presure	0.5 hPa (20 °C)
Appearance	Liquid
Color	Clear yellow to brown
Odor	Moderate aniline-type.
Exposure Limit	NIOSH REL: TWA 0.5 ppm (2 mg/m3), IDLH 100 ppm; OSHA PEL: TWA 2ppm (9 mg/m3); ACGIH TLV: TWA 0.5 ppm (adopted).
Merck	14,6019
BRN	741982
pKa	4.84(at 25℃)
PH	7.6 (1g/l, H2O, 20℃)
Storage Condition	Store below +30°C.
Stability	Stability Combustible. Incompatible with strong oxidizing agents. Discolours upon exposure to air.
Sensitive	Air Sensitive
Refractive Index	n20/D 1.571(lit.)
Physical and Chemical Properties	Colorless to red-brown oily flammable liquid. melting point -57 ℃ boiling point 196.25 ℃ relative density 0.9891 refractive index 1.5684 solubility: slightly soluble in water, soluble in ethanol, ether, chloroform.
Use	Used as a dye intermediate

N-methylaminobenzene - Risk and Safety

Risk Codes	R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R33 - Danger of cumulative effects R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Description	S28 - After contact with skin, wash immediately with plenty of soap-suds. S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S28A -
UN IDs	UN 2294 6.1/PG 3
WGK Germany	3
RTECS	BY4550000
FLUKA BRAND F CODES	8
TSCA	Yes
HS Code	29214200
Hazard Class	6.1
Packing Group	III
Toxicity	LD in rabbits (g/kg): 0.28 orally; in rabbits, cats (mg/kg): 24, 24 i.v. (Treon)

N-methylaminobenzene - Upstream Downstream Industry

Raw Materials	Aniline Methyl alcohol
Downstream Products	1,3-dimethyl-1,3-diphenylurea N-benzyl-N-methylaniline 2-(N-methylanilino)ethanol Buprofezin

N-methylaminobenzene - Nature

Open Data Verified Data

colorless to red-brown oily flammable liquid. The relative density was 0.9891. Melting Point -57 °c. Boiling point 196. 25 °c. Refractive index 5684. Long-term storage color change. Slightly soluble in water, soluble in ethanol, ether, chloroform.

Last Update：2024-01-02 23:10:35

N-methylaminobenzene - Preparation Method

Open Data Verified Data

aniline and methanol were catalyzed by copper-zinc-chromium catalyst to produce crude products, which were removed by simple distillation and vacuum distillation to remove methanol, water, aniline, N-methylaniline was followed by the final product.

Last Update：2022-01-01 10:52:10

N-methylaminobenzene - Use

Open Data Verified Data

useful as an intermediate in organic synthesis, as a solvent and as an acid acceptor.

Last Update：2022-01-01 10:52:09

N-methylaminobenzene - Safety

Open Data Verified Data

rabbit oral LD50 280mg/kg, the highest allowable concentration in the air of the workplace 5 x 10 -6. Production equipment should be closed. The operator should wear protective gear.
packaged in iron drum, 180kg per barrel. Store in a ventilated place to protect against heat and moisture.

Last Update：2022-01-01 10:52:10

N-methylaminobenzene - Reference Information

Henry's Law Constant	(x 10-5 atm?m3/mol):1.19 at 25 °C (approximate - calculated from water solubility and vapor pressure)
LogP	1.66 at 20℃
NIST chemical information	information provided by: webbook.nist.gov (external link)
EPA chemical substance information	information provided by: ofmpeb.epa.gov (external link)
Overview	N-methylaniline is the main product in the N-alkyl Arylamine series and is an important intermediate in fine chemicals. It is widely used. The first set of production equipment in China was aided by the former Soviet Union in the 50's. The products are mainly used in the production of explosives, which are commonly used in the blending of straight-run gasoline, therefore, some technicians use straight-run gasoline as the base oil of blended gasoline, and increase the octane number by adding N-methyl aniline, so as to achieve the purpose of saving investment and high efficiency.
Introduction	N-methylaniline colorless oily liquid at room temperature. Soluble in ethanol, ether, chloroform, insoluble in water, not easy to evaporative loss, but is not conducive to the distribution of multi-cylinder engine cylinder. Stable nature, in the air and dark environment is not easy to decompose. The main features of blended gasoline added with N-methyl aniline antiknock agent are odor, high density, unstable unwashed colloid, low olefin value, and need to be assisted with antiknock agents such as MTBE and MMT.
Application	N-methylaniline is a widely used fine chemical product, mainly used in the production of pesticides, dyes, dye Intermediates, rubber additives and explosives, and can be used as solvents and acid acceptors, as intermediates in organic synthesis, acid absorbents and solvents. The dye industry is used for the production of cationic brilliant red FG, cationic Pink B, activated yellow brown KGR, etc. It can also be used to improve the octane number of gasoline and organic synthesis, and can also be used as a solvent.
properties	colorless to reddish brown oily flammable liquid. Soluble in ethanol, ether, chloroform, water-soluble. Placement of gradient yellow.
Application	used as a dye intermediate N-methylaniline is both a raw material for the insecticide Buprofezin, it is used for the synthesis of its intermediate N-chloromethyl N-phenylcarbamoyl chloride, and is also an intermediate of the herbicide benzoylamine. In addition, it is widely used in the dye industry. The product is used as an intermediate in organic synthesis, an acid absorbent and a solvent, and is used in the production of cationic brilliant red FG, cationic Pink B, activated yellow brown KGR and the like in the dye industry. N-methylaniline is used as an intermediate in organic synthesis, an acid absorbent and a solvent, and in the dye industry for the production of cationic brilliant red FG, cationic Pink B, activated yellow brown KGR, etc.
production method	There are several methods: aniline vapor is mixed with dimethyl ether, the reaction was carried out at 230-295 °c. N-methylaniline was synthesized from aniline and methanol in the presence of lead-zinc-chromium catalyst. Then methanol, water, aniline and N,N-dimethylaniline were removed by distillation to obtain N-methylaniline product. The reaction can also be carried out in the presence of phosphorus trichloride (aniline: methanol: phosphorus trichloride = 1:0.9:0.003mol). In laboratory preparations, dimethyl sulfate may be used as the methylating agent. Dimethyl sulfate was added dropwise to a mixture of 10% or less aniline and water, stirred for 1H, and then added dropwise with a 30% sodium hydroxide solution. The upper organic phase was separated by standing, and the lower layer was extracted with benzene. After the benzene was recovered from the extract, the resulting oily matter was combined with the organic phase, I .e., a mixture of aniline, N-methylaniline and N,N-dimethylaniline. The mixture was treated with sulfuric acid. The mixture was treated with sulfuric acid to filter out crystals of aniline-forming sulfate. N,N-dimethylaniline can be converted to N-methylaniline by the following reaction with acetic anhydride. Industrial N-methyl aniline content is greater than or equal to 98%. Raw material consumption quota: aniline 1200kg/t, methanol 700kg/t. N-methyl aniline mainly has the following several synthesis methods. The crude N-methylaniline was formed from aniline and methanol under the action of copper, zinc and chromium catalyst, and then methanol, water, aniline and N,N-dimethylaniline were removed by distillation to obtain crude N-methylaniline, the product was then distilled under vacuum. Aniline was reacted with dimethyl sulfate. Dimethyl sulfate was added dropwise to a mixture of aniline and water at 10 ° C. Or lower, stirred for 1H, and then added dropwise with a 30% sodium hydroxide solution. The layer was separated by standing, the upper layer was organic phase, and the lower layer was extracted with benzene, After the extraction of benzene, the resulting oil was combined with the organic phase to obtain a mixture of aniline, N-methylaniline and N,N-dimethylaniline. The mixture was treated with sulfuric acid to filter out crystals of aniline-forming sulfate. N,N-dimethylaniline can be converted to N-methylaniline by the following reaction.
category	toxic substances
toxicity grade	poisoning
Acute toxicity	oral-rabbit LDL0: 280 mg/kg; Oral-guinea pig LDL0: 1200 mg/m3
flammability hazard characteristics	open flame flammable; High heat releases toxic nitrogen oxide gas
storage and transportation characteristics	The warehouse is ventilated and dried at low temperature; It is stored separately from oxidants and food and chemical additives
extinguishing agent	dry powder, foam, carbon dioxide, sand
Occupational Standard	TWA 2.2 mg/m3; Tel 7 mg/m3
spontaneous combustion temperature	500°C
toxic substance data	information provided by: pubchem.ncbi.nlm.nih.gov (external link)
immediate life-and health-threatening concentration	100 ppm

Last Update：2024-04-09 19:55:45

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