174849-24-2

Basic information

• Product Name: (S)-2-(hydroxy)-2-phenyl-propanonitrile
• Synonyms: (S)-2-(hydroxy)-2-phenyl-propanonitrile
• CAS NO: 174849-24-2
• Molecular Weight: 147.177
• Mol File: 174849-24-2.mol

Chemical Properties

• CAS DataBase Reference: (S)-2-(hydroxy)-2-phenyl-propanonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(hydroxy)-2-phenyl-propanonitrile(174849-24-2)
• EPA Substance Registry System: (S)-2-(hydroxy)-2-phenyl-propanonitrile(174849-24-2)

Safety Data

• Hazardous Substances Data: 174849-24-2(Hazardous Substances Data)

Upstream product

• 74-90-8 hydrogen cyanide 
• 98-86-2 acetophenone 
• 29624-91-7 1-cyano-1-phenylethyl acetate 
• 252966-52-2 (S)-2-trimethylsiloxy-2-phenyl propionitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 20102-12-9 2-hydroxy-2-phenylpropionitrile 

Downstream Products

• 252966-52-2 (S)-2-trimethylsiloxy-2-phenyl propionitrile 
• 1092081-12-3 (S)-1-cyano-1-phenylethyl (S)-2-methoxy-2-phenylacetate 
• 1092081-10-1 (S)-1-cyano-1-phenylethyl (R)-2-methoxy-2-phenylacetate 
• 319449-13-3 C₉H₇NO₃ 
• 98-85-1 1-Phenylethanol 

Relevant articles and documents

Optimized catalysts for the asymmetric addition of trimethylsilyl cyanide to aldehydes and ketones

A bimetallic titanium(IV)salen complex has been developed as an exceptionally active catalyst for the asymmetric addition of trimethylsilyl cyanide to ketones. For the corresponding addition to aldehydes, a vanadium(IV)salen complex was found to give high

Hydroxynitrile lyase in organic solvent-free systems to overcome thermodynamic limitations

The overcoming of thermodynamic limitations in the synthesis of optically active ketone cyanohydrins by using organic solvent-free systems has been investigated. Therefore, substrates with known unfavorable results within hydroxynitrile lyase-catalyzed re

Hydrolase-catalysed preparation of chiral a,a-disubstituted cyanohydrin acetates

The enzymatic hydrolysis of esters of tertiary alcohols has long been a challenge. In particular their kinetic resolutions have virtually not been addressed. Here we describe the successful kinetic resolution of a,a-disubstituted cyanohydrin acetates, a t

Cross-linked aggregates of the hydroxynitrile lyase from Manihot esculenta: Highly active and robust biocatalysts

The precipitation and cross-linking into CLEAs of the hydroxynitrile lyase (E.G. 4.1.2.10) from Manihot esculenta was investigated and an optimized procedure, which involved precipitation with (NH4)2SO 4, was developed. It

Enzymatic Synthesis of (R)-Cyanohydrins by Three (R)-Oxynitrilase Sources in Micro-aqueous Organic Medium

The enantioselective synthesis of optically active (R)-cyanohydrins generated from several aromatic, heteroaromatic and aliphatic aldehydes and methyl ketones was carried out using almond, peach or loquat meal as (R)-oxynitrilase sources in diisopropylether under micro-aqueous conditions The micro-aqueous reaction system, which is superior to the conventionally used water-organic biphase reaction system, performed well over the temperature range of 4 deg C to 30 deg C.

Synthesis of (R)-cyanohydrins by crude (R)-oxynitrilase-catalyzed reactions in micro-aqueous medium

In diisopropyl ether or ethyl acetate under micro-aqueous conditions, the enantioselective synthesis of (R)-cyanohydrins from aldehydes and methyl ketones was studied using crude (R)-oxynitrilase prepared from almonds. This reaction system performed well

Enzyme catalysed formation of (S)-cyanohydrins derived from aldehydes and ketones in a biphasic solvent system

By employing a vigorously stirred two phase system aqueous buffer/organic solvent and using the hydroxynitrile lyase from Hevea brasiliensis as biocatalyst enantiopure (S)-cyanohydrins from aliphatic, unsaturated, aromatic and heteroaromatic aldehydes and methyl alkyl and methyl phenyl ketones are obtained in high yield and in general 98-99% enantiomeric excess.

Catalytic asymmetric synthesis of (S)-acetophenone cyanohydrin under high pressure

The first trimethylsilylcyanation of acetophenone to its (S)-cyanohydrin was accomplished with e.e. up to 60% in 93% yield at 0.8 GPa, using 0.01 eq. of a reuseable catalyst prepared from (S)-3,3-dimethyl-1,2,4-butanetriol and titanium isopropoxide. Reactions of 4'-substituted acetophenones to the corresponding cyanohydrins gave lower e.e. and yields.

Approach to (R)- and (S)-ketone cyanohydrins using almond and apple meal as the source of (R)-oxynitrilase

The synthesis of aliphatic and aromatic (R)-ketone cyanohydrins through the addition of hydrogen cyanide to the corresponding ketones and the synthesis of the (S)-enantiomers through the kinetic resolution of racemic ketone cyanohydrins has been studied in the presence of almond or apple meal. Substrate tolerance of the (R)-oxynitrilases towards ketones (R1R2C=O) is highly restricted compared to that of structurally similar aldehydes, reactivity following the order of H>Me>>Et for R2. In the case of aromatic methyl ketones reactivity difference (C6H5>>p-Me-C6H4 for R1) is notable.

Ueber die erste rekombinante Hydroxynitril-Lyase und ihre Anwendung in der Synthese von (S)-Cyanhydrinen

Keywords: Asymmetrische Synthesen; (S)-Cyanhydrine; Enzymkatalyse; Lyasen