(S)-3-(4'-fluorophenyl)-3-hydroxypropanenitrile

Base Information

• Chemical Name: (S)-3-(4'-fluorophenyl)-3-hydroxypropanenitrile
• CAS No.: 1044833-25-1
• Molecular Formula: C₉H₈FNO
• Molecular Weight: 165.167
• Mol file: 1044833-25-1.mol

Synonyms:(S)-3-(4'-fluorophenyl)-3-hydroxypropanenitrile

Chemical Property of (S)-3-(4'-fluorophenyl)-3-hydroxypropanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-(4'-fluorophenyl)-3-hydroxypropanenitrile

There total 8 articles about (S)-3-(4'-fluorophenyl)-3-hydroxypropanenitrile 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: 90.0%

3-(4-fluorophenyl)-3-oxopropionitrile (4640-67-9) → (S)-3-(4'-fluorophenyl)-3-hydroxypropanenitrile (1044833-25-1,522629-15-8)

Guidance literature:

With alpha-D-glucopyranose; glucose dehydrogenase from Bacillus megaterium; benzil reductase; nicotinamide adenine dinucleotide phosphate; In dimethyl sulfoxide; at 30 ℃; for 24h; pH=8; enantioselective reaction; Enzymatic reaction;

DOI:10.1016/j.tet.2016.05.027

Reference yield:

sodium cyanide (773837-37-9) + 4-fluorostyrene oxide (18511-62-1,53631-23-5,134356-73-3,134356-74-4) → (S)-3-(4'-fluorophenyl)-3-hydroxypropanenitrile (1044833-25-1,522629-15-8) + R-(-)-2-(4-fluorophenyl)oxirane (18511-62-1,53631-23-5,134356-74-4,134356-73-3) + (2S)-2-(4-fluorophenyl)oxirane (18511-62-1,53631-23-5,134356-73-3,134356-74-4)

Guidance literature:

With halohydrin dehalogenase from Agrobacterium radiobacter AD₁, mutant W₂₄₉P; In aq. phosphate buffer; dimethyl sulfoxide; at 20 ℃; for 2h; pH=7; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/j.catcom.2021.106285

Reference yield:

(RS)-3-(4-fluorophenyl)-3-hydroxypropionitrile (136568-65-5,522629-15-8) → (R)-3-(4'-fluorophenyl)-3-hydroxypropanenitrile (522629-15-8) + (S)-3-(4'-fluorophenyl)-3-hydroxypropanenitrile (1044833-25-1,522629-15-8) + (R)-(+)-3-(4-fluorophenyl)-3-hydroxypropionic acid + (S)-(-)-3-(4-fluorophenyl)-3-hydroxypropionic acid

Guidance literature:

With potassium phosphate buffer; nitrilase bll6402; at 30 ℃; pH=7.2; Title compound not separated from byproducts;

DOI:10.1021/ol061542+

upstream raw materials:

(RS)-3-(4-fluorophenyl)-3-hydroxypropionitrile

3-(4-fluorophenyl)-3-oxopropionitrile

4-fluorobenzoyl chloride

4-fluorobenzoic acid ethyl ester

Refernces

• 1、 Deng, Boxin,Cheng, Tanyu,Wu, Meng,Wang, Jinyu,Liu, Guohua. "Enantioselective reduction of α-Cyano and α-Nitro substituted acetophenones promoted by a bifunctional mesoporous silica". . p. 2856 - 2860. Retrieved 2013.
• 2、 Annunziata, Francesca,Conti, Paola,Gandolfi, Raffaella,Guaglio, Alessandra,Tamborini, Lucia. "Continuous-flow stereoselective reduction of prochiral ketones in a whole cell bioreactor with natural deep eutectic solvents". . p. 950 - 956. Retrieved 2022/02/02.
• 3、 Saito, Akira,Adachi, Shinya,Kumagai, Naoya,Shibasaki, Masakatsu. "Direct Catalytic Asymmetric Addition of Alkylnitriles to Aldehydes with Designed Nickel–Carbene Complexes". supporting information. p. 8739 - 8743. Retrieved 2021/03/16.