7462-76-2

Basic information

• Product Name: 2-CHLORO-2-PHENYLACETAMIDE
• Synonyms: 2-CHLORO-2-PHENYLACETAMIDE;AURORA KA-7239;2-chloro-2-phenyl-ethanamide
• CAS NO: 7462-76-2
• Molecular Formula: C₈H₈ClNO
• Molecular Weight: 169.61
• Mol File: 7462-76-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 328.2°Cat760mmHg
• Flash Point: 152.3°C
• Appearance: /
• Density: 1.254g/cm³
• Vapor Pressure: 0.000193mmHg at 25°C
• Refractive Index: 1.567
• CAS DataBase Reference: 2-CHLORO-2-PHENYLACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-2-PHENYLACETAMIDE(7462-76-2)
• EPA Substance Registry System: 2-CHLORO-2-PHENYLACETAMIDE(7462-76-2)

Safety Data

• Hazardous Substances Data: 7462-76-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H8ClNO/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11)

Upstream product

• 22259-83-2 2-chloro-2-phenylacetonitrile 
• 4410-31-5 (RS)-mandelamide 
• 6476-18-2 4-phenyl-pyrrolidine-2,3,5-trione 
• 7732-18-5 water 
• 14380-61-1 hypochlorite 
• 532-28-5 (RS)-mandelonitrile 
• 1336-21-6 ammonium hydroxide 
• 2912-62-1 α-chlorophenylacetyl chloride 
• 401582-20-5 2-chloro-N-(4-methoxybenzyl)-2-phenylethanamide 

Downstream Products

• 7253-67-0 (R,S)-1-(1-piperidino)phenylacetamide 
• 22259-83-2 (R)-chloro-phenyl-acetonitrile 
• 1733-63-7 1,2,2-triphenylethan-1-one 
• 22259-83-2 2-chloro-2-phenylacetonitrile 
• 856065-63-9 optically inactive 2.3-diphenyl-succinic acid diamide 
• 100542-70-9 (4-chloro-phenylsulfanyl)-phenyl-acetic acid amide 
• 15146-07-3 meso-1,2-dicyano-1,2-diphenylethane 
• 15307-93-4 N-phenyl-2,6-dichloroaniline 
• 312757-92-9 [3-cyano-4-(2-methoxyphenyl)-6-phenylpyridin-2-ylsulfanyl]phenylacetamide 

Relevant articles and documents

One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles

We have identified a novel one-pot method for the synthesis of β-amino alcohols, which is based on C-H bond hydroxylation at the benzylic α-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target. This journal is

Formation of Carbonyl Compounds from Amines through Oxidative C-N Bond Cleavage using Visible Light Photocatalysis and Applications to N-PMB-Amide Deprotection

A method has been developed for C-N bond cleavage that utilizes visible light photocatalysis. The process, which utilizes 1 mol% of the ruthenium complex Ru(bpy)3Cl2 as the photocatalyst, potassium persulfate (K2S2O8) as the oxidant and water/acetonitrile (H2O/CH3CN) as the solvent, transforms a variety of primary, secondary and tertiary amines to the corresponding carbonyl compounds. In addition, this method was applied to the removal of a p-methoxylbenzyl (PMB) group from N-PMB protected amides.

Nitrile hydratase activity of a recombinant nitrilase

Appreciable amounts of amide are formed in the course of nitrile hydrolysis in the presence of recombinant nitrilase from Pseudomonas fluorescens EBC 191, depending on the α-substituent and the reaction conditions. The ratio of the nitrilase and nitrile hydratase activities of the enzyme is profoundly influenced by the electronic and steric properties of the reactant. In general, amide formation increased when the α-substituent was electron-deficient; 2-chloro-2-phenylacetonitrile, for example, afforded 89% amide. We found, moreover, that (R)-mandelo-nitrile was hydrolysed with 11% of amide formation whereas 55% amide was formed from the (S)-enantiomer; a similar effect was found for the O-acetyl derivatives. A mechanism that accomodates our results is proposed.