(S)-Hydroxyphenylacetonitrile

Base Information

• Chemical Name: (S)-Hydroxyphenylacetonitrile
• CAS No.: 28549-12-4
• Molecular Formula: C8H7NO
• Molecular Weight: 133.15
• Mol file: 28549-12-4.mol

Synonyms:(S)-Hydroxy(phenyl)acetonitrile;(S)-Mandelonitrile;(S)-Benzaldehyde cyanohydrin;(2S)-Hydroxy(phenyl)ethanenitrile;

Chemical Property of (S)-Hydroxyphenylacetonitrile

Chemical Property:

• Boiling Point: 282.7 °C at 760 mmHg
• PKA: 10.50±0.20(Predicted)
• Flash Point: 97.2 °C
• Density: 1.169 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

95% ^*data from raw suppliers

(S)-2-Hydroxy-2-phenylacetonitrile 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-Hydroxyphenylacetonitrile

There total 61 articles about (S)-Hydroxyphenylacetonitrile 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%

hydrogen cyanide (74-90-8) + benzaldehyde (100-52-7) → (S)-mandelonitrile (28549-12-4)

Guidance literature:

In di-isopropyl ether; at 25 ℃; for 7h; hydroxynitrile lyase (S)-MeHNL (EC 4.1.2.37), nitrocellulose;

Reference yield: 99.0%

trimethylsilyl cyanide (7677-24-9) + benzaldehyde (100-52-7) → (S)-mandelonitrile (28549-12-4)

Guidance literature:

With 4 A molecular sieve; dimethylaluminum chloride; Triphenylphosphine oxide; (R)-BINOLAM; In toluene; at -20 ℃; for 6h;

DOI:10.1021/ol0262338

Reference yield: 93.0%

(R)-((R)-1-Methyl-3-oxo-butoxy)-phenyl-acetonitrile (86013-39-0) → (R)-Mandelonitrile (10020-96-9) + (S)-mandelonitrile (28549-12-4)

Guidance literature:

With toluene-4-sulfonic acid; In 1,4-dioxane; water; for 16h; Heating;

DOI:10.1021/jo00161a035

upstream raw materials:

vinyl acetate

(RS)-mandelonitrile

cyano(phenyl)methyl acetate

2-(Butyryloxy)-2-phenylethannitril

Downstream raw materials:

(S)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-heptylamine

(R)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-heptylamine

(S)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-hexylamine

(R)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-hexylamine

Refernces

• 1、 Torrelo, Guzman,Van Midden, Nelleke,Stloukal, Radek,Hanefeld, Ulf. "Immobilized hydroxynitrile lyase: A comparative study of recyclability". . p. 1096 - 1102. Retrieved 2014.
• 2、 Coloma, José,Guiavarc'h, Yann,Hagedoorn, Peter-Leon,Hanefeld, Ulf. "Probing batch and continuous flow reactions in organic solvents:Granulicella tundricolahydroxynitrile lyase (GtHNL)". . p. 3613 - 3621. Retrieved 2020/06/25.
• 3、 Nuylert, Aem,Motojima, Fumihiro,Khanongnuch, Chartchai,Hongpattarakere, Tipparat,Asano, Yasuhisa. "Stabilization of Hydroxynitrile Lyases from Two Variants of Passion Fruit, Passiflora edulis Sims and Passiflora edulis Forma flavicarpa, by C-Terminal Truncation". . p. 181 - 189. Retrieved 2019/12/12.