940-47-6

Basic information

• Product Name: Phenoxymethyl chloromethyl ketone
• Synonyms: 1-Chloro-3-phenoxy-2-propanone;1-Chloro-3-phenoxyacetone;Phenoxymethyl chloromethyl ketone;1-chloro-3-phenoxypropan-2-one
• CAS NO: 940-47-6
• Molecular Formula: C₉H₉ClO₂
• Molecular Weight: 185
• Mol File: 940-47-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 33-34℃
• Boiling Point: 274℃
• Flash Point: 117℃
• Appearance: /
• Density: 1.191
• CAS DataBase Reference: Phenoxymethyl chloromethyl ketone(CAS DataBase Reference)
• NIST Chemistry Reference: Phenoxymethyl chloromethyl ketone(940-47-6)
• EPA Substance Registry System: Phenoxymethyl chloromethyl ketone(940-47-6)

Safety Data

• Hazardous Substances Data: 940-47-6(Hazardous Substances Data)

Usage

General Description

Phenoxymethyl chloromethyl ketone is a chemical compound with the formula C10H14ClNO2. It is widely used as a potential irritant in riot control agents, and it is classified as a Schedule 3 substance under the Chemical Weapons Convention due to its potential for use as a chemical warfare agent. Phenoxymethyl chloromethyl ketone is also a potent irreversible inhibitor of the enzyme alpha-chymotrypsin, and it has been studied for its potential use in pharmaceutical research. However, its use is controversial due to its potential for harm in both riot control and warfare scenarios, as well as its potential for misuse in chemical weapons.

Upstream product

• 4769-73-7 (RS)-1-chloro-3-phenyloxy-2-propanol 
• 2564-83-2 2,2,6,6-tetramethyl-piperidine-N-oxyl 
• 2065-23-8 methyl 2-phenoxyacetate 
• 186581-53-3 diazomethane 
• 701-99-5 Phenoxyacetyl chloride 
• 21443-40-3 1-Diazo-3-phenoxy-2-propanone 

Downstream Products

• 78946-50-6 C₉H₈ClNO₃ 
• 75-66-1 2-methylpropan-2-thiol 
• 62569-84-0 1-Chlor-2-deuterio-3-phenoxy-2-propanol 
• 4769-73-7 (RS)-1-chloro-3-phenyloxy-2-propanol 
• 90354-26-0 1-chloro-2-methyl-3-phenoxypropan-2-ol 
• 90354-27-1 2-Chloromethyl-1-phenoxy-butan-2-ol 
• 82430-43-1 (S)-3-chloro-1-phenoxy-2-propanol 
• 140630-37-1 (2R)-1-azido-3-phenoxypropan-2-ol 
• 349080-71-3 (S)-3-hydroxy-4-(phenyloxy)butanenitrile 
• 86728-93-0 methyl (S)-4-chloro-3-hydroxybutanoate 
• 141942-84-9 (R)-methyl (3-hydroxy-4-cyano)-butanoate 
• 62372-05-8 1-(N-Propionyl-isopropylamino)-3-phenoxy-2-propionyloxy-propan 
• 62569-85-1 2-Deuterio-1-isopropylamino-3-phenoxy-2-propanol 
• 62372-04-7 1-(N-Methyl-isopropylamino)-3-phenoxy-2-propanol 

Relevant articles and documents

Biocatalytic cascade for the synthesis of enantiopure β-azidoalcohols and β-hydroxynitriles

A three-step, two-enzyme, one-pot reaction sequence starting from prochiral a-chloroketones leading to enantiopure (3- azidoalcohols and (3-hydroxynitriles is described. Asymmetric bioreduction of a-chloroketones by hydrogen transfer catalysed by an alcohol dehydrogenase (ADH) established the stereogenic centre in the first step to furnish enantiopure chlorohydrin intermediates. Subsequent biocatalysed ring closure to the epoxide and nucleophilic ring opening with azide, N3-, or cyanide, CN-, both catalysed by a nonselective halohydrin dehalogenase (Hhe) proceeded with full retention of configuration to give enantiopure (-azidoalcohols and (3-hydroxynitriles, respectively. Both enantiomers of various optically pure (-azidoalcohols and (-hydroxynitriles were synthesised.

PROCESS FOR THE PREPARATION OF ALPHA-CHLOROKETONES FROM ALKYL ESTERS

The present invention relates to a process for the preparation of α-chloroketones from readily available alkyl esters by the reaction of a sulfoxonium ylide on said alkyl esters to generate a keto sulfoxonium ylide that is in turn treated with anhydrous HCl.

One-Carbon Chain Extension of Esters to α-Chloroketones: A Safer Route without Diazomethane

The reaction of a variety of methyl esters with dimethylsulfoxonium methylide at 0-25 °C affords the chain-extended β-keto dimethylsulfoxonium ylides. Subsequent treatment with hydrogen chloride in THF proceeds with loss of DMSO to afford the corresponding α-chloroketones. This sequence has been utilized to convert the methyl esters of CBZ-protected alanine and valine to the anti N-protected α-amino epoxides, which are important pharmaceutical intermediates. When the same protocol is applied to BOC-protected phenylalanine methyl ester, epimerization occurs so that the use of a more reactive aryl ester is required. This chemistry provides a practical route to α-chloroketones that avoids the use of toxic and explosive diazomethane.