15190-67-7

Basic information

• Product Name: Benzeneacetonitrile, a-(methylphenylamino)-
• CAS NO: 15190-67-7
• Molecular Formula: C15H14N2
• Molecular Weight: 222.29
• Mol File: 15190-67-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzeneacetonitrile, a-(methylphenylamino)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetonitrile, a-(methylphenylamino)-(15190-67-7)
• EPA Substance Registry System: Benzeneacetonitrile, a-(methylphenylamino)-(15190-67-7)

Safety Data

• Hazardous Substances Data: 15190-67-7(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 100-61-8 N-methylaniline 
• 98-88-4 benzoyl chloride 
• 1934-92-5 N-methyl-N-phenyl-benzamide 
• 7677-24-9 trimethylsilyl cyanide 
• 532-28-5 (RS)-mandelonitrile 

Downstream Products

• 69905-90-4 (E)-2-(Methyl-phenyl-amino)-2-phenyl-hex-4-enenitrile 
• 43006-71-9 1-(N-Methylanilino)-1-phenylpropen 
• 32897-40-8 N-methyl-N-(1-phenylethenyl)aniline 
• 128407-52-3 2-(Methyl-phenyl-amino)-5-oxo-2,3,5-triphenyl-pentanenitrile 
• 614-30-2 N-methyl-N-phenyl-benzenemethanamine 
• 87531-37-1 α-(N-methylanilino)-α,α'-diphenylazine 
• 128407-43-2 (Z)-2-(Methyl-phenyl-amino)-5-morpholin-4-yl-2,3,5-triphenyl-pent-4-enenitrile 
• 69905-83-5 2-(N-methyl-N-phenylamino)-2-phenylpropanenitrile 
• 69905-84-6 2-(Methyl-phenyl-amino)-2-phenyl-butyronitrile 

Relevant articles and documents

Are multicomponent strecker reactions of diketones with diamines under high pressure amenable to heterocyclic synthesis?

Employing double Strecker strategy, two new heterocyclic compounds, 5,6,11,12-tetrahydro-6,11-dimethyldibenzo[b,f][1,4]diazocine-6,11-dicarbonitrile and 1,2,3,4,5,10-hexahydrophenazine-4a, 10a-dicarbonitrile, were prepared in one step albeit in low yields. The reaction has proven to be very limited, but such a sterically hindered amine as N-methylaniline underwent Strecker reaction with benzaldehyde and TMSCN to give the corresponding α-amino nitriles.

Iridium-Catalyzed Reductive Strecker Reaction for Late-Stage Amide and Lactam Cyanation

A new iridium-catalyzed reductive Strecker reaction for the direct and efficient formation of α-amino nitrile products from a broad range of (hetero)aromatic and aliphatic tertiary amides, and N-alkyl lactams is reported. The protocol exploits the mild and highly chemoselective reduction of the amide and lactam functionalities using IrCl(CO)[P(C6H5)3]2 (Vaska's complex) in the presence of tetramethyldisiloxane, as a reductant, to directly generate hemiaminal species able to undergo substitution by cyanide upon treatment with TMSCN (TMS=trimethylsilyl). The protocol is simple to perform, broad in scope, efficient (up to 99 % yield), and has been successfully applied to the late-stage functionalization of amide- and lactam-containing drugs, and naturally occurring alkaloids, as well as for the selective cyanation of the carbonyl carbon atom linked to the N atom of proline residues within di- and tripeptides.