Benzeneacetonitrile, 4-fluoro-alpha-hydroxy-, (alphaR)- (9CI)

Base Information

• Chemical Name: Benzeneacetonitrile, 4-fluoro-alpha-hydroxy-, (alphaR)- (9CI)
• CAS No.: 149952-37-4
• Molecular Formula: C8H6 F N O
• Molecular Weight: 151.14
• Mol file: 149952-37-4.mol

Synonyms:Benzeneacetonitrile,4-fluoro-a-hydroxy-, (R)-;(+)-2-Hydroxy-2-(4-fluorophenyl)acetonitrile

Chemical Property of Benzeneacetonitrile, 4-fluoro-alpha-hydroxy-, (alphaR)- (9CI)

Chemical Property:

• PSA: 44.02000
• LogP: 1.38268

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzeneacetonitrile, 4-fluoro-alpha-hydroxy-, (alphaR)- (9CI)

There total 14 articles about Benzeneacetonitrile, 4-fluoro-alpha-hydroxy-, (alphaR)- (9CI) 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: 93.0%

hydrogen cyanide (74-90-8) + 4-fluorobenzaldehyde (459-57-4) → (R)-2-(4-fluorophenyl)-2-hydroxyacetonitrile (149952-37-4,176485-58-8)

Guidance literature:

With hydroxynitrile lyase isozyme 5 from Prunus communis; In tert-butyl methyl ether; at 25 ℃; for 7h; pH=5; Enzymatic reaction;

DOI:10.1002/adsc.201601332

Reference yield: 75.0%

trimethylsilyl cyanide (7677-24-9) + 4-fluorobenzaldehyde (459-57-4) → (R)-2-(4-fluorophenyl)-2-hydroxyacetonitrile (149952-37-4,176485-58-8)

Guidance literature:

4-fluorobenzaldehyde; With (S)-[1,1']-binaphthalenyl-2,2'-diol; lithium isopropoxide; In toluene; for 0.166667h; Cooling with acetone-dry ice; Inert atmosphere;

trimethylsilyl cyanide; In toluene; for 1.25h; Cooling; Inert atmosphere;

With hydrogenchloride; In methanol; toluene; at 20 ℃; Inert atmosphere;

Reference yield: 73.0%

4-fluorobenzaldehyde (459-57-4) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → (R)-2-(4-fluorophenyl)-2-hydroxyacetonitrile (149952-37-4,176485-58-8)

Guidance literature:

With (R)-oxynitrilase; In di-isopropyl ether; at 20 ℃; for 6h; Enzymatic reaction;

DOI:10.21608/ejchem.2017.3262

upstream raw materials:

hydrogen cyanide

4-fluorobenzaldehyde

trimethylsilyl cyanide

potassium cyanide

Downstream raw materials:

(R)-2-(6-chloro-pyrimidin-4-ylamino)-1-(4-fluoro-phenyl)-ethanol

(R)-2-amino-1-(4-fluoro-phenyl)-ethanol hydrochloride

(R)-2-(4-fluorophenyl)-2-hydroxyacetic acid

Refernces

• 1、 Zheng, Yu-Cong,Ding, Liang-Yi,Jia, Qiao,Lin, Zuming,Hong, Ran,Yu, Hui-Lei,Xu, Jian-He. "A High-Throughput Screening Method for the Directed Evolution of Hydroxynitrile Lyase towards Cyanohydrin Synthesis". . p. 996 - 1000. Retrieved 2021/01/15.
• 2、 Yosef, Hisham Abdallah A.,Elmasry,Ibrahim, Nabila M.,Ismael, Eman H. I.,Mahran. "Preparation and reactions of certain racemic and optically active cyanohydrins derived from 2-chlorobenzaldehyde, 4-fluorobenzaldehyde, benzo[d][1,3]-dioxole-5-carbaldehyde and 2,3-dihydrobenzo[b][1,4]dioxine-6-carbaldehyde. Antimicrobial and in vitro antitumor evaluation of the products". . p. 301 - 328. Retrieved 2017/06/08.