82782-11-4

Basic information

• Product Name: Benzenepropanenitrile, b-(acetyloxy)-
• CAS NO: 82782-11-4
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.214
• Mol File: 82782-11-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzenepropanenitrile, b-(acetyloxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanenitrile, b-(acetyloxy)-(82782-11-4)
• EPA Substance Registry System: Benzenepropanenitrile, b-(acetyloxy)-(82782-11-4)

Safety Data

• Hazardous Substances Data: 82782-11-4(Hazardous Substances Data)

Upstream product

• 1006-66-2 5-phenyl-4,5-dihydroisoxazole 
• 614-16-4 Benzoylacetonitrile 
• 73627-97-1 3-hydroxy-3-phenylpropanenitrile 
• 96-09-3 styrene oxide 
• 75-36-5 acetyl chloride 
• 127081-13-4 β-chlorobenzenepropanenitrile 
• 64-19-7 acetic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 24506-17-0 ethyl (R)-3-hydroxy-3-phenylbutanoate 
• 1885-38-7 cinnamic nitrile 
• 21087-76-3 (S)-3-acetoxy-3-phenylpropanenitrile 
• 73627-97-1 (R)-3-phenyl-3-hydroxypropanenitrile 
• 132203-26-0 (S)-3-hydroxy-3-phenylpropanenitrile 
• 198561-42-1 (R)-3-acetyloxy-3-phenylpropanenitrile 

Relevant articles and documents

Chemoenzymatic synthesis2 of both enantiomers of fluoxetine, tomoxetine and nisoxetine: Lipase-catalyzed resolution of 3-aryl-3-hydroxypropanenitriles

A facile preparation of (±)-3-hydroxy-3-phenylpropanenitrile has been carried out by ring-opening of styrene oxide with NaCN in aqueous ethanol. Subsequent kinetic resolution of this material via lipase-mediated transesterification gave the S-alcohol and R-acetate in excellent yields and high enantioselectivities, particularly with lipase PS-C 'Amano' II. The effect of solvents and immobilization of the lipase has also been investigated. It is interesting to note that the use of immobilized lipase for this transesterification process in hydrophobic solvents (diisopropyl ether, toluene and hexane) enhanced the reaction rate drastically and gave optimal yields with high enantioselectivity (>99%). Moreover, enantiopure 3-hydroxy-3-phenylpropanenitrile products have been converted via enantioconvergent routes into the (R)- and (S)-enantiomers of the important anti-depressants fluoxetine, tomoxetine, nisoxetine and norfluoxetine.

Zinc-Promoted Reactions. 9. The Fate of the Cyano Group in the Reduction of Simple Cyanoketones and N-Cyanoamines

The Zn/AcOH reduction of 1 leads only to the carbonyl reduction, while C-decyanation occurs in the case of 2.The mechanism of the latter reaction is discussed.The N-decyanation of N-cyanoamines 3 and 4 involves an ionic mechanism, leading to N-acyl derivatives and isocyanic acid, the latter compound being ultimately reduced to formic acid.