(2R)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile

Base Information

• Chemical Name: (2R)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile
• CAS No.: 71962-66-8
• Molecular Formula: C14H11 N O2
• Molecular Weight: 225.247
• Mol file: 71962-66-8.mol

Synonyms:Benzeneacetonitrile,a-hydroxy-3-phenoxy-, (R)-; (R)-a-Cyano-3-phenoxybenzyl alcohol

Chemical Property of (2R)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile

Chemical Property:

• Vapor Pressure: 4.13E-07mmHg at 25°C
• Boiling Point: 399.8°C at 760 mmHg
• Flash Point: 195.6°C
• PSA: 53.25000
• Density: 1.22g/cm³
• LogP: 3.03588

Purity/Quality:

98%min ^*data from raw suppliers

(αR)-α-Hydroxy-3-phenoxybenzeneacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (αR)-α-Hydroxy-3-phenoxybenzeneacetonitrile is used as a reagent in the synthesis of (1R)-trans-Lambda-Cyhalothrin (L170000); an isomer of λ-Cyhalothrin (C988980) which is used as an insecticide.

Technology Process of (2R)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile

There total 34 articles about (2R)-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: 49.0%

alpha-cyano-3-phenoxybenzyl acetate (61066-87-3) → O-acetyl-(R)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile (126641-87-0) + (S)-m-phenoxybenzaldehyde cyanohydrin (39515-47-4,52315-06-7,61826-76-4,71962-66-8)

Guidance literature:

With Arthrobacter lipase; In water; at 40 ℃; for 23h; Yields of byproduct given; pH 4;

upstream raw materials:

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

hydrogen cyanide

Downstream raw materials:

esfenvalerate

[R]-alpha-cyano-3-phenoxybenzyl [S]-2-(4-chlorophenyl)-2-isopropyl-acetate

<1R,1α(S^*),3α(E)>-1-Cyano-1-(3-phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(tert-butylsulfonyl)-3-oxo-1-propenyl>cyclopropanecarboxylate

<1R,1α(S^*),3α(E)>-1-Cyano-1-(3-phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(phenylsulfonyl)-3-oxo-1-propenyl>cyclopropanecarboxylate

Refernces

• 1、 Jangir, Nisha,Preeti,Padhi, Santosh Kumar. "A study on increasing enzymatic stability and activity of Baliospermum montanum hydroxynitrile lyase in biocatalysis". . p. 78 - 89. Retrieved 2019/11/05.
• 2、 Zheng, Yu-Cong,Xu, Jian-He,Wang, Hui,Lin, Guo-Qiang,Hong, Ran,Yu, Hui-Lei. "Hydroxynitrile Lyase Isozymes from Prunus communis: Identification, Characterization and Synthetic Applications". supporting information. p. 1185 - 1193. Retrieved 2017/04/13.