559334
3-Hydroxy-3-phenylpropionitrile
Synonym(s):
β-Hydroxy-benzenepropanenitrile
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About This Item
Linear Formula:
C6H5CH(OH)CH2CN
CAS Number:
Molecular Weight:
147.17
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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
13 - Non Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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D Brady et al.
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.
Granander J, et al.
Tetrahedron Asymmetry, 17(13), 2021-2027 (2006)
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