(S)-2-Hydroxy-2-(3-phenoxyphenyl)acetonitrile

Base Information

• Chemical Name: (S)-2-Hydroxy-2-(3-phenoxyphenyl)acetonitrile
• CAS No.: 61826-76-4
• Molecular Formula: C₁₄H₁₁NO₂
• Molecular Weight: 225.247
• Hs Code.: 2926909090
• European Community (EC) Number: 441-070-6
• DSSTox Substance ID: DTXSID301031526
• Nikkaji Number: J291.130B
• Mol file: 61826-76-4.mol

Synonyms:61826-76-4;(S)-2-Hydroxy-2-(3-phenoxyphenyl)acetonitrile;(S)-3-Phenoxybenzaldehyde cyanohydrin;(S)-3-Phenoxy-mandelonitrile;(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile;(S)-alpha-cyano-3-phenoxybenzyl alcohol;(S)-alpha-hydroxy-3-phenoxy-benzeneacetonitrile;EC 441-070-6;SCHEMBL1677135;GXUQMKBQDGPMKZ-CQSZACIVSA-N;DTXSID301031526;(s)-a-cyano-3-phenoxybenzyl alcohol;MFCD01937336;AKOS016008005;(S)alpha-cyano-3-phenoxybenzyl alcohol;FS-3727;(S)alpha-cyano-3-phenoxy-benzyl alcohol;(2S)-Hydroxy(3-phenoxyphenyl)acetonitrile;CS-0031366;(S)alpha-hydroxy-3-phenoxy-benzene-acetonitrile;EN300-7372430;A868629;Benzeneacetonitrile, .alpha.-hydroxy-3-phenoxy-, (.alpha.S)-;(S)-2-HYDROXY-2-(3-PHENOXYPHENYL)ACETONITRILE (CONTAINS ~9% ETHYL ACETATE)

Chemical Property of (S)-2-Hydroxy-2-(3-phenoxyphenyl)acetonitrile

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.607
• Boiling Point: 399.828 °C at 760 mmHg
• PKA: 10.33±0.20(Predicted)
• Flash Point: 195.609 °C
• PSA: 53.25000
• Density: 1.221 g/cm³
• LogP: 3.03588
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 225.078978594
• Heavy Atom Count: 17
• Complexity: 277

Purity/Quality:

99% ^*data from raw suppliers

(S)-2-Hydroxy-2-(3-phenoxyphenyl)acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OC2=CC=CC(=C2)C(C#N)O
• Isomeric SMILES: C1=CC=C(C=C1)OC2=CC=CC(=C2)[C@@H](C#N)O

Technology Process of (S)-2-Hydroxy-2-(3-phenoxyphenyl)acetonitrile

There total 21 articles about (S)-2-Hydroxy-2-(3-phenoxyphenyl)acetonitrile 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: 99.0%

hydrogen cyanide (74-90-8) + 3-Phenoxybenzaldehyde (39515-51-0) → (S)-m-phenoxybenzaldehyde cyanohydrin (39515-47-4,52315-06-7,61826-76-4,71962-66-8)

Guidance literature:

With hydroxynitrile lyase from Hevea brasiliensis; In water; at 15 ℃; for 0.25h; pH 5.5;

DOI:10.1016/S0040-4020(98)00901-6

Reference yield: 92.0%

O-acetyl-(S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile (113301-28-3) → (S)-m-phenoxybenzaldehyde cyanohydrin (39515-47-4,52315-06-7,61826-76-4,71962-66-8)

Guidance literature:

With ethanol; In di-isopropyl ether; at 25 ℃; for 6h; lipase from Pseudomonas cepacia (Amano);

DOI:10.1021/jo00047a016

Reference yield: 85.0%

(R,S)-cyano(3-phenoxyphenyl)methyl butyrate (120838-94-0) → (S)-m-phenoxybenzaldehyde cyanohydrin (39515-47-4,52315-06-7,61826-76-4,71962-66-8) + (R)-cyano(3-phenoxyphenyl)methyl butanoate

Guidance literature:

With Pseudomonas cepacia lipase immobilised in a gelatin matrix; butan-1-ol; In hexane; for 8h;

DOI:10.1016/S0957-4166(00)00303-7

upstream raw materials:

O-acetyl-(S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile

alpha-cyano-3-phenoxybenzyl acetate

(2R,4S)-4-Methyl-2-(3-phenoxy-phenyl)-[1,3]dioxane

(4S,6S)-4,6-Dimethyl-2-(3-phenoxy-phenyl)-[1,3]dioxane

Downstream raw materials:

Fenvalerate

esfenvalerate

λ-cyhalothrin

(S)-α-cyano-3-phenoxybenzyl (Z)-(1R,3R)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropane carboxylate

Refernces

• 1、 Jangir, Nisha,Padhi, Santosh Kumar. "Immobilized Baliospermum montanum hydroxynitrile lyase catalyzed synthesis of chiral cyanohydrins". . p. 32 - 40. Retrieved 2018/11/27.
• 2、 Chu, Chang-Ying,Hsu, Chu-Tin,Lo, Po Hsiang,Uang, Biing-Jiun. "Enantioselective silylcyanation of aldehydes catalyzed by new chiral oxovanadium complex". scheme or table. p. 1981 - 1984. Retrieved 2012/03/10.