13312-84-0

Basic information

• Product Name: Benzeneacetonitrile, 2-chloro-a-hydroxy-
• Synonyms: Mandelonitrile, o-chloro-(6CI,7CI,8CI);(o-Chlorophenyl)glycolonitrile;(?à)-2-Chloromandelonitrile;2-Chlorobenzaldehyde cyanohydrin;2-Chloromandelonitrile;o-Chlorobenzaldehyde cyanohydrin;o-Chloromandelonitrile
• CAS NO: 13312-84-0
• Molecular Formula: C₉H₉ClO₃
• Molecular Weight: 167.595
• Mol File: 13312-84-0.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 143.253 °C
• Flash Point: 143.253 °C
• Density: 1.332 g/cm³
• CAS DataBase Reference: Benzeneacetonitrile, 2-chloro-a-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetonitrile, 2-chloro-a-hydroxy-(13312-84-0)
• EPA Substance Registry System: Benzeneacetonitrile, 2-chloro-a-hydroxy-(13312-84-0)

Safety Data

• Hazardous Substances Data: 13312-84-0(Hazardous Substances Data)

Usage

General Description

Benzeneacetonitrile, 2-chloro-a-hydroxy-, also known as 2-chlorophenylglycolic acid nitrile, is a chemical compound with the molecular formula C8H6ClNO. It is a colorless to light brown liquid with a faint, pleasant odor. 2-chlorophenylglycolic acid nitrile is used as an intermediate in the production of agricultural chemicals, pharmaceuticals, and other organic compounds. It is also used in the synthesis of various fine chemicals and as a chemical intermediate in the manufacture of a wide variety of products. Additionally, it is considered to be a potential environmental contaminant and poses a risk to human health and the environment if released into the air, water, or soil.

Upstream product

• 151-50-8 potassium cyanide 
• 89-98-5 2-chloro-benzaldehyde 
• 66985-47-5 2-chloro-α-[(trimethylsilyl)oxy]benzeneacetonitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 773837-37-9 sodium cyanide 
• 74-90-8 hydrogen cyanide 
• 108-24-7 acetic anhydride 

Downstream Products

• 32345-59-8 methyl (R)-2-chloromandelate 
• 156276-21-0 rac-methyl 2-chloromandelate 
• 1584127-56-9 methyl 2-acetoxy-2-(2-chlorophenyl)acetate 
• 1184446-14-7 2-(2-chlorophenyl)-2-((4-methoxyphenyl)amino)acetonitrile 
• 125803-35-2 2-acetoxy-2-(2-chlorophenyl)acetonitrile 
• 10421-85-9 (S)-2-chloromandelic acid 
• 10421-85-9 (R)-2-chloromandelic acid 
• 52923-20-3 (S)-2-(2-chlorophenyl)-2-hydroxyacetonitrile 
• 100865-42-7 (2-chloro-phenyl)-(toluene-4-sulfonyloxy)-acetonitrile 
• 3876-09-3 5-(2-chloro-phenyl)-4,5-dihydro-oxazol-2-ylamine 
• 178437-75-7 2-acetoxy-2-(2-chlorophenyl)acetic acid 
• 2444-36-2 2'-chloro-benzeneacetic acid 

Relevant articles and documents

CO2-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions**

Thermodynamic and kinetic control of a chemical process is the key to access desired products and states. Changes are made when a desired product is not accessible; one may manipulate the reaction with additional reagents, catalysts and/or protecting groups. Here we report the use of carbon dioxide to accelerate cyanohydrin synthesis under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN. Under inert atmosphere, the reaction is essentially not operative due to the unfavored equilibrium. The utility of CO2-mediated selective cyanohydrin synthesis was further showcased by broadening Kiliani–Fischer synthesis under neutral conditions. This protocol offers an easy access to a variety of polyols, cyanohydrins, linear alkylnitriles, by simply starting from alkyl- and arylaldehydes, KCN and an atmospheric pressure of CO2.

Refining method of high-purity O-chloromandelonitrile

The invention provides a refining method of high-purity o-chloromandelonitrile. The refining method comprises: (a) carrying out pressure reducing distillation on an o-chloromandelonitrile mother liquor to obtain a concentrated liquid; (b) adding the concentrated liquid obtained in the step (a) into an alkane-based solvent to obtain a mixed solution; and (c) cooling the mixed solution obtained in the step (b) to a temperature of 0-10 DEG C, crystallizing, carrying out suction filtration, and drying to obtain o-chloromandelonitrile. According to the present invention, the method has characteristics of simple operation, high product purity and high yield.

Hydroxynitrile Lyase Isozymes from Prunus communis: Identification, Characterization and Synthetic Applications

Biocatalysts originating from Badamu (Prunus communis) have been applied to catalyze the asymmetric synthesis of (R)-4-methylsulfanylmandelonitrile, a key building block of thiamphenicol and florfenicol. Here, four hydroxynitrile lyase (HNL) isozymes from Badamu were cloned and heterologously expressed in Pichia pastoris. The biochemical properties and catalytic performances of these isozymes were comprehensively explored to evaluate their efficiency and selectivity in asymmetric synthesis. Among then, PcHNL5 was identified with outstanding activity and enantioselectivity in asymmetric hydrocyanation. Under the optimized mild biphasic reaction conditions, seventeen prochiral aromatic aldehydes were converted to valuable chiral cyanohydrins with good yields (up to 94%) and excellent optical purities (up to >99.9% ee), which provide a facile access to numerous chiral amino alcohols, hypoglycemic agents, angiotension converting enzyme (ACE) inhibitors and β-blockers. This work therefore underlines the importance of discovering the most potent biocatalyst among a group of isozymes for converting unnatural substrates into value-added products. (Figure presented.).