559334
3-Hydroxy-3-phenylpropionitrile
Synonym(s):
β-Hydroxy-benzenepropanenitrile
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About This Item
form
solid
refractive index
n20/D 1.5420 (lit.)
bp
306-307 °C (lit.)
density
1.112 g/mL at 25 °C (lit.)
SMILES string
OC(CC#N)c1ccccc1
InChI
1S/C9H9NO/c10-7-6-9(11)8-4-2-1-3-5-8/h1-5,9,11H,6H2
InChI key
HILDHWAXSORHRZ-UHFFFAOYSA-N
General description
3-Hydroxy-3-phenylpropionitrile, a β-hydroxynitrile, is an aryl substituted α-aminophenylaceronitrile. It can be obtained by reacting lithioacetonitrile with benzaldehyde via asymmetric 1,2-addition reaction.
Application
Reactant for:
- Hydrolysis by cyanobacterium nitrilase in catalytic preparation of carboxylic acid
- Biotransformation to amide using nitrile hydratase from Rhodococcus erythropolis A4
- Direct catalytic aldol-type reactions
Storage Class Code
13 - Non Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Applied microbiology and biotechnology, 64(1), 76-85 (2003-12-11)
Biocatalytic transformations converting aromatic and arylaliphatic nitriles into the analogous related amide or acid were investigated. These studies included synthesis of the beta-substituted nitrile 3-hydroxy-3-phenylpropionitrile, subsequent enrichment and isolation on this substrate of nitrile-degrading microorganisms from the environment, and a
Highly enantioselective 1, 2-additions of various organolithium reagents to aldehydes.
Tetrahedron Asymmetry, 17(13), 2021-2027 (2006)
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