17583-40-3

Basic information

• Product Name: 2-(methylamino)benzonitrile
• Synonyms: 2-(methylamino)benzonitrile;Benzonitrile,2-(methylamino)-
• CAS NO: 17583-40-3
• Molecular Formula: C₈H₈N₂
• Molecular Weight: 132
• Mol File: 17583-40-3.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 277.6 °C at 760 mmHg
• Flash Point: 121.7°C
• Appearance: /
• Density: 1.06 g/cm³
• Vapor Pressure: 0.00448mmHg at 25°C
• Refractive Index: 1.551
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 2-(methylamino)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(methylamino)benzonitrile(17583-40-3)
• EPA Substance Registry System: 2-(methylamino)benzonitrile(17583-40-3)

Safety Data

• Hazardous Substances Data: 17583-40-3(Hazardous Substances Data)

Usage

General Description

2-(methylamino)benzonitrile, also known as N-methyl-2-aminobenzonitrile, is a chemical compound with the molecular formula C8H8N2. It is a white to pale yellow solid and is classified as an aromatic amine. It is used in the production of pharmaceuticals, dyes, and other organic compounds. 2-(methylamino)benzonitrile is also used as a building block in organic synthesis and as an intermediate in the production of various chemicals. It is important to handle this compound with care, as it may be harmful if inhaled, swallowed, or absorbed through the skin.

InChI:InChI=1/C8H8N2/c1-10-8-5-3-2-4-7(8)6-9/h2-5,10H,1H3

Upstream product

• 77-78-1 dimethyl sulfate 
• 1885-29-6 anthranilic acid nitrile 
• 13061-96-6 dihydroxy-methyl-borane 
• 74-89-5 methylamine 
• 616-38-6 carbonic acid dimethyl ester 
• 614-00-6 N-methyl-N-nitrosoaniline 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 110-54-3 hexane 
• 394-47-8 2-fluorobenzonitrile 
• 6832-87-7 2-bromo-N-methylaniline 
• 68-12-2 N,N-dimethyl-formamide 
• 199472-00-9 (E)-2-[(2-Bromo-phenyl)-methyl-amino]-4-phenyl-but-3-enenitrile 
• 199471-96-0 2-(N-methyl-o-bromoanilino)hept-3-enenitrile 
• 199471-98-2 4-methyl-2-(N-methyl-o-bromoanilino)-3-pentenenitrile 

Downstream Products

• 28531-05-7 (2-(methylamino)phenyl)(thiophen-2-yl)methanone 
• 59338-13-5 2-(4,5-dihydro-1H-imidazol-2-yl)-N-methyl-aniline 
• 30091-22-6 2-(N-methyl-N-nitrosoamino)benzonitrile 
• 85-91-6 Methyl N-methylanthranilate 
• 64605-29-4 1-(2-(methylamino)phenyl)-2-phenylethanone 
• 1859-76-3 2-(methylamino)benzophenone 
• 122908-19-4 cyclohexyl(2-(methylamino)phenyl)methanone 
• 32606-05-6 2-N-methylaminophenyl isopropyl ketone 

Relevant articles and documents

Nickel/Photo-Cocatalyzed Asymmetric Acyl-Carbamoylation of Alkenes

An unprecedented asymmetric acyl-carbamoylation of pendant alkenes tethered on aryl carbamic chlorides with both aliphatic and aromatic aldehydes has been developed via the cooperative catalysis of a chiral nickel-PHOX complex and tetrabutylammonium decatungstate. This reaction represents the first example of merging hydrogen-atom-transfer photochemistry and asymmetric transition metal catalysis in difunctionalization of alkenes. Using this protocol, a variety of oxindoles bearing a challenging quaternary stereogenic center are furnished under mild conditions in highly enantioselective manner.

Selective N-monomethylation of primary anilines with dimethyl carbonate in continuous flow

Selective N-monomethylation of anilines has been achieved under continuous flow conditions using dimethyl carbonate as a green methylating agent in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene. Our methodology takes advantage of the expanded process windows available in the continuous flow regime to safely induce monomethylation in superheated solvents at high pressure. We propose selective N-monomethylation is achieved via an in situ protection-deprotection pathway, which is supported by the observed reactivities of several putative reaction intermediates. The robust and scalable method was applicable to a broad range of primary aniline substrates including ortho-, meta-, and para-substituted anilines, as well as electron-rich and electron-deficient anilines. The synthetic precursor of diazepam, 5-chloro-2-(methylamino)benzophenone, was selectively synthesized under our optimized conditions.

Rhodium(III)-Catalyzed Direct Cyanation of Aromatic C-H Bond to Form 2-(Alkylamino)benzonitriles Using N-Nitroso As Directing Group

2-(Alkylamino)benzonitriles were synthesized via a rhodium-catalyzed cyanation on the aryl C-H bond and subsequent denitrosation of N-nitrosoarylamines using a removable nitroso as the directing group, in which N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) was used as the "CN" source. Various substituents on the aryl ring and amino group of N-nitrosoarylamines tolerated the reaction, and the corresponding products were achieved in moderate to good yields.