(S)-3-hydroxy-3-phenylpropanenitrile

Base Information

Chemical Name:(S)-3-hydroxy-3-phenylpropanenitrile
CAS No.:132203-26-0
Molecular Formula:C₉H₉NO
Molecular Weight:147.177
Hs Code.:
European Community (EC) Number:859-640-1
Nikkaji Number:J380.067I

Synonyms:(3S)-3-hydroxy-3-phenylpropanenitrile;(S)-3-hydroxy-3-phenylpropanenitrile;132203-26-0;SCHEMBL1546681;HILDHWAXSORHRZ-VIFPVBQESA-N;(S)-3-phenyl-3-hydroxypropionitrile;(S)-beta-Hydroxybenzenepropanenitrile;(S)-3-phenyl-3-hydroxypropanenitrile;AT30394;CS-0246854;EN300-3450962

Suppliers and Price of (S)-3-hydroxy-3-phenylpropanenitrile

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

American Custom Chemicals Corporation
(3S)-3-HYDROXY-3-PHENYLPROPANENITRILE 95.00%
5MG
$ 502.19

Total 3 raw suppliers

Chemical Property of (S)-3-hydroxy-3-phenylpropanenitrile

Chemical Property:

XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:147.068413911
Heavy Atom Count:11
Complexity:152

Purity/Quality:

95% ^*data from raw suppliers

(3S)-3-HYDROXY-3-PHENYLPROPANENITRILE 95.00% ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:C1=CC=C(C=C1)C(CC#N)O
Isomeric SMILES:C1=CC=C(C=C1)[C@H](CC#N)O
General Description (S)-3-Hydroxy-3-phenylpropanenitrile, also referred to as (S)-β-hydroxy nitrile, is an enantiomerically enriched compound synthesized via biocatalytic reduction of β-keto nitriles, such as 3-oxo-3-phenylpropanenitrile, using microbial systems like *Curvularia lunata* or engineered bakers' yeast reductases. This chiral intermediate serves as a key precursor for pharmaceuticals like fluoxetine, atomoxetine, and nisoxetine. The reduction can be optimized to achieve high enantioselectivity and minimize competing side reactions, such as alkylation, through enzyme engineering or whole-cell biocatalysis. (S)-3-hydroxy-3-phenylpropanenitrile's synthesis benefits from alcohol additives or methanol cosolvents, which enhance reaction rates and selectivity in both chemical and enzymatic processes.

Technology Process of (S)-3-hydroxy-3-phenylpropanenitrile

There total 131 articles about (S)-3-hydroxy-3-phenylpropanenitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

: 614-16-4
Benzoylacetonitrile

: 132203-26-0
(S)-3-hydroxy-3-phenylpropanenitrile

Guidance literature:: With formic acid; RuCl(p-cymene)[N-(p-tosyl)-(1R,2R)-diphenylethylenediamine]; triethylamine; at 30 ℃; for 24h;
DOI:10.1021/jo011076w

Reference yield: 99.0%

: 614-16-4
Benzoylacetonitrile

: 73627-97-1,121617-17-2,132203-26-0,17190-29-3
3-hydroxy-3-phenylpropanenitrile

Guidance literature:: With formic acid; C₁₈H₂₄ClIrN₃; In water; at 80 ℃; for 3h; chemoselective reaction; Schlenk technique; Inert atmosphere;
DOI:10.1039/c8gc00348c

Reference yield: 98.0%

: 96-09-3
styrene oxide

: potassium cyanide

: 73627-97-1,121617-17-2,132203-26-0,17190-29-3
3-hydroxy-3-phenylpropanenitrile

Guidance literature:: styrene oxide; potassium cyanide; In acetonitrile; at 20 ℃; for 0.0833333h;

With 2,2'-(1,2-phenylenediylbisnitrilomethylidine)bis(4-hydroxyphenolato)nickel(II); In acetonitrile; at 20 ℃; for 0.416667h; Reagent/catalyst; Time; Solvent; regioselective reaction;
DOI:10.1016/j.poly.2012.10.019