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559334

Sigma-Aldrich

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.[1] It can be obtained by reacting lithioacetonitrile with benzaldehyde via asymmetric 1,2-addition reaction.[2]

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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Highly enantioselective 1, 2-additions of various organolithium reagents to aldehydes.
Granander J, et al.
Tetrahedron Asymmetry, 17(13), 2021-2027 (2006)
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

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