360557-73-9

Basic information

• Product Name: (S)-chloro-phenyl-acetic acid amide
• CAS NO: 360557-73-9
• Molecular Weight: 169.611
• Mol File: 360557-73-9.mol

Chemical Properties

• CAS DataBase Reference: (S)-chloro-phenyl-acetic acid amide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-chloro-phenyl-acetic acid amide(360557-73-9)
• EPA Substance Registry System: (S)-chloro-phenyl-acetic acid amide(360557-73-9)

Safety Data

• Hazardous Substances Data: 360557-73-9(Hazardous Substances Data)

Upstream product

• 532-28-5 (RS)-mandelonitrile 
• 22259-83-2 2-chloro-2-phenylacetonitrile 

Relevant articles and documents

Probing the enantioselectivity of a diverse group of purified cobalt-centred nitrile hydratases

In this study a diverse range of purified cobalt containing nitrile hydratases (NHases, EC 4.2.1.84) from Rhodopseudomonas palustris HaA2 (HaA2), Rhodopseudomonas palustris CGA009 (009), Sinorhizobium meliloti 1021 (1021), and Nitriliruptor alkaliphilus (iso2), were screened for the first time for their enantioselectivity towards a broad range of chiral nitriles. Enantiomeric ratios of >100 were found for the NHases from HaA2 and CGA009 on 2-phenylpropionitrile. In contrast, the Fe-containing NHase from the well-characterized Rhodococcus erythropolis AJ270 (AJ270) was practically aselective with a range of different α-phenylacetonitriles. In general, at least one bulky group in close proximity to the α-position of the chiral nitriles seemed to be necessary for enantioselectivity with all NHases tested. Nitrile groups attached to a quaternary carbon atom were only reluctantly accepted and showed no selectivity. Enantiomeric ratios of 80 and >100 for AJ270 and iso2, respectively, were found for the pharmaceutical intermediate naproxennitrile, and 3-(1-cyanoethyl)benzoic acid was hydrated to the corresponding amide by iso2 with an enantiomeric ratio of >100.

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.