6740-85-8

Basic information

• Product Name: 2-Chlorophenyl cyclopentyl ketone
• Synonyms: 0-chlorphenylcyclopentylketone;Methanone, (2-chlorophenyl)cyclopentyl-;2-Chlorophenyl cyclopentyl;O-Chlorphenyl Cyclopentyl Ketone;(2-Chlorophenyl)-cyclopentylketone/2-ChlorophenylCyclopentanone/ O-Chlorphenyl Cyclopentyl Ketone/2-ChlorophenylCyclopentylKetone/ O-ChlorophenylCyclopentylKetone/(2-Chlorophenyl)cyclopentylketone ;2-CHLORPHENYL CYCLOPENTYL KETONE;o-Chlorphenyl cyclophentyl ketone;20Chlorophenylcyclopentylketone
• CAS NO: 6740-85-8
• Molecular Formula: C₁₂H₁₃ClO
• Molecular Weight: 208.68
• EINECS: 229-802-0
• Mol File: 6740-85-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 96
• Boiling Point: 96°C
• Flash Point: >100°C
• Appearance: liquid
• Density: 1.16
• Vapor Pressure: 0.00283mmHg at 25°C
• Refractive Index: 1.5470
• Storage Temp.: Refrigerator
• Solubility: Slightly miscible with chloroform and ethyl acetate.
• BRN: 1873022
• CAS DataBase Reference: 2-Chlorophenyl cyclopentyl ketone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chlorophenyl cyclopentyl ketone(6740-85-8)
• EPA Substance Registry System: 2-Chlorophenyl cyclopentyl ketone(6740-85-8)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 6740-85-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 6740-85-8 differently. You can refer to the following data:
1. 2-Chlorophenyl Cyclopentyl Ketone is used as a reagent in the preparation of bicyclic and polycyclic aromatic hydrocarbons.
2. 2-Chlorophenyl cyclopentyl ketone is used as a reagent in the preparation of bicyclic and polycyclic aromatic hydrocarbons. It acts as a pharmaceutical intermediate and also as an intermediate of ketamine.

InChI:InChI=1/C12H13ClO/c13-11-8-4-3-7-10(11)12(14)9-5-1-2-6-9/h3-4,7-9H,1-2,5-6H2

Upstream product

• 106961-64-2 (2-chlorophenyl)(cyclopent-1-en-1-yl)methanone 
• 936-52-7 1-(N-morpholino)cyclopent-1-ene 
• 609-65-4 o-chlorobenzoyl chloride 
• 106961-63-1 (2-Chloro-phenyl)-(2-morpholin-4-yl-cyclopent-1-enyl)-methanone 
• 137-43-9 Cyclopentyl bromide 
• 873-32-5 2-Chlorobenzonitrile 
• 120-92-3 cyclopentanone 
• 17529-98-5 cyclopentanone p-tolylsulfonylhydrazone 
• 89-98-5 2-chloro-benzaldehyde 
• 19833-92-2 1-(2-chlorophenyl)(cyclopentyl)methanol 
• 33240-34-5 cyclopentylmagnesium bromide 
• 142-29-0 cyclopentene 
• 4524-93-0 Cyclopentanecarboxylic acid chloride 
• 1034156-02-9 o-chlorophenylmagnesium chloride 

Downstream Products

• 6740-86-9 (1-Bromocyclopentyl)(2-chlorophenyl)methanone 
• 79499-57-3 (±)-1-((2-chlorophenyl)(imino)methyl)cyclopentan-1-ol 
• 35211-10-0 norketamine 
• 79499-58-4 1-<(2-Chlorophenyl)iminomethyl>cyclopentanol hydrochloride 
• 83777-65-5 (S)-Norketamine 
• 120199-64-6 (2R,6S)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexan-1-one 

Relevant articles and documents

Preparation method of high-purity esketamine hydrochloride ketone body

The invention discloses a preparation method of a high-purity esketamine hydrochloride ketone body. The structure of the esketamine hydrochloride ketone body is shown as a formula (I). The preparationmethod comprises the following steps of: by taking cyclopentanoic acid and o-chlorobromobenzene as starting materials, carrying out acylating chlorination reaction, metallization reaction and Grignard reaction to synthesize the esketamine hydrochloride ketone body. The esketamine hydrochloride ketone body obtained by the method has the characteristics of high purity, high yield, capability of being applied to preparation of esketamine hydrochloride bulk drugs and the like.

Process Research and Impurity Control Strategy of Esketamine

An improved synthesis of (S)-ketamine (esketamine) has been developed, which was cost-effective, and the undesired isomer could be recovered by racemization. Critical process parameters of each step were identified as well as the process-related impurities. The formation mechanisms and control strategies of most impurities were first discussed. Moreover, the (S)-ketamine tartrate is a dihydrate, which was disclosed for the first time. The practicable racemization catalyzed by aluminum chloride was carried out in quantitative yield with 99% purity. The ICH-grade quality (S)-ketamine hydrochloride was obtained in 51.1% overall yield (14.0% without racemization) by chiral resolution with three times recycling of the mother liquors. The robust process of esketamine could be industrially scalable.

Method for synthesizing chiral alcohol through deracemization

The invention relates to a method for synthesizing chiral alcohol (formula I) through deracemization. The preparation method provided by the invention is one-pot asymmetric cascade reaction, and comprises the following steps: 1), with racemic alcohol (formula II) as a raw material and dipropylene glycol dimethyl ether as a solvent, reacting at 120 DEG C for 12 hours, and performing a dehydrogenation reaction to produce intermediate ketone (formula III); and 2), directly adding 2.5mol% of a chiral diamine metal ruthenium complex as a catalyst into a reaction system, with 5 equivalents of sodiumformate as a hydrogen source and a mixed solution of methanol and water as a solvent, reacting at 50 DEG C for 12 hours under the protection of nitrogen, and performing asymmetric transfer hydrogenation to obtain the chiral alcohol (formula I). The method has the advantages of environment-friendly synthesis such as a simple and mild reaction condition, step economy and atomic economy; and in addition, a substrate has a wide application range, the enantioselectivity is high, and the method has a broad application prospect in synthesis of chiral alcohol pharmaceutical intermediates and fine chemical raw materials.