N-Methylaniline

Base Information

• Chemical Name: N-Methylaniline
• CAS No.: 100-61-8
• Molecular Formula: C6H5NH(CH3)
• Molecular Weight: 107.155
• Hs Code.: 2921.42
• European Community (EC) Number: 202-870-9
• ICSC Number: 0921
• NSC Number: 3502
• UN Number: 2294
• UNII: TH45GK410O
• DSSTox Substance ID: DTXSID9021841
• Nikkaji Number: J3.591B
• Wikipedia: N-Methylaniline
• Wikidata: Q1959597
• Metabolomics Workbench ID: 49836
• ChEMBL ID: CHEMBL170781
• Mol file: 100-61-8.mol

Synonyms:methylaniline;methylaniline hydrochloride;monomethylaniline;N-methylaniline

Chemical Property of N-Methylaniline

Chemical Property:

• Appearance/Colour: pale yellow to brown liquid
• Vapor Pressure: 0.325mmHg at 25°C
• Melting Point: -57 °C(lit.)
• Refractive Index: n20/D 1.571(lit.)
• Boiling Point: 196.249 °C at 760 mmHg
• PKA: 4.84(at 25℃)
• Flash Point: 78.889 °C
• PSA: 12.03000
• Density: 0.984 g/cm³
• LogP: 1.80130
• Storage Temp.: Store below +30°C.
• Sensitive.: Air Sensitive
• Solubility.: water: slightly soluble30g/L
• Water Solubility.: 30 g/L
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 107.073499291
• Heavy Atom Count: 8
• Complexity: 55.4
• Transport DOT Label: Poison

Purity/Quality:

95%/98%99% ^*data from raw suppliers

N-Methylaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 23/24/25-33-50/53
• Safety Statements: 28-36/37-45-60-61-28A

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: CNC1=CC=CC=C1
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.
• Physical properties: Colorless to yellow to pale brown liquid with a faint, ammonia-like odor. Odor threshold concentration is 1.7 ppm (quoted, Amoore and Hautala, 1983).
• Uses: N-Methylaniline is used as a solvent and in organic synthesis. It is used in the production of cationic brilliant red FG, cationic pink B, reactive yellow brown KGR, etc. in the dye industry. N-methylaniline is an intermediate in the synthesis of the insecticide buprofezin and the herbicide mefenacet.

Technology Process of N-Methylaniline

There total 851 articles about N-Methylaniline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

N-methyl-N-phenylbenzimidamide (57767-07-4) → benzonitrile (100-47-0) + N-methylaniline (100-61-8)

Guidance literature:

With bis(trimethylsilyl)amide yttrium(III); In toluene; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1039/c8cy01481g

Reference yield: 90.0%

N-methyl-N-phenyl-benzamide (1934-92-5) → N-methylaniline (100-61-8) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With hydrogen; sodium methylate; In methanol; at 100 ℃; for 16h; under 37503.8 Torr; Product distribution / selectivity; Autoclave;

Reference yield: 87.0%

C13H13N3 → pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4) + N-methylaniline (100-61-8)

Guidance literature:

With bis(trimethylsilyl)amide yttrium(III); In toluene; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1039/c8cy01481g

upstream raw materials:

methanol

aniline hydrochloride

aniline hydrobromide

methyl magnesium iodide

Downstream raw materials:

N-(2-hydroxyethyl)-N-methylaminobenzene

1-ethyl-N²-methyl-N²-phenyl-ethanediyldiamine

methyl-phenyl-(tetrahydropyran-2-yl)amine

N-methyl-N-(2-[2]pyridyl-ethyl)-aniline

Refernces

Asymmetric Cycloisomerization of o-Alkenyl-N-Methylanilines to Indolines by Iridium-Catalyzed C(sp³)?H Addition to Carbon–Carbon Double Bonds

10.1002/anie.201708578

The research focuses on the asymmetric cycloisomerization of o-alkenyl-N-methylanilines to indolines through iridium-catalyzed C(sp3)-H addition to carbon-carbon double bonds. The study establishes a highly enantioselective method for the synthesis of indolines bearing quaternary stereogenic carbon centers at the 3-positions, using an iridium catalyst with a bidentate chiral diphosphine ligand. The experiments involved the reaction of N-methylanilines with o-alkenyl groups in the presence of an iridium catalyst precursor and various chiral phosphorus ligands, with toluene as the solvent at temperatures ranging from 80 to 135°C. The reactants included a range of N-methylaniline derivatives with different substituents on the aniline ring and the double bond. The analyses used to determine the success of the reactions included isolated yields, enantiomeric excess (ee) determined by supercritical fluid chromatography (SFC) with a chiral stationary phase column, and deuterium labeling experiments to probe the reaction mechanism. The study also proposed a reaction mechanism based on the experimental results, which involves rate-determining oxidative addition of the N-methyl C-H bond, followed by intramolecular carboiridation and reductive elimination.