10498-35-8

Basic information

• Product Name: CIS-1,2-DICHLOROCYCLOHEXANE
• Synonyms: cyclohexane,1,2-dichloro-,cis-;CIS-1,2-DICHLOROCYCLOHEXANE;TIMTEC-BB SBB007831;(1R,2S)-1,2-Dichlorocyclohexane
• CAS NO: 10498-35-8
• Molecular Formula: C₆H₁₀Cl₂
• Molecular Weight: 153.05
• Mol File: 10498-35-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: -1.5°C
• Boiling Point: 181.5°C (rough estimate)
• Flash Point: 66.1 °C
• Appearance: /
• Density: 1.2021
• Vapor Pressure: 0.333mmHg at 25°C
• Refractive Index: 1.4967
• CAS DataBase Reference: CIS-1,2-DICHLOROCYCLOHEXANE(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-1,2-DICHLOROCYCLOHEXANE(10498-35-8)
• EPA Substance Registry System: CIS-1,2-DICHLOROCYCLOHEXANE(10498-35-8)

Safety Data

• Hazardous Substances Data: 10498-35-8(Hazardous Substances Data)

Usage

Uses

cis-1,2-Dichlorocyclohexane is used in preparation of organic halides from organotellurium(IV) halides by elimination reaction.

InChI:InChI=1/C6H10Cl2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4H2/t5-,6+

Upstream product

• 930-66-5 1-chlorocyclohexene 
• 6628-80-4 trans-2-chlorocyclohexanol 
• 2108-92-1 1,1-dichlrocyclohexane 
• 27334-16-3 2-Chlorocyclohexyltellurium trichloride 
• 286-20-4 cyclohexane-1,2-epoxide 
• 30011-03-1 N,N-Dimethyl-(2-chlorcyclohexyl-oxymethylen)-immoniumchlorid 
• 110-83-8 cyclohexene 
• 110-86-1 pyridine 
• 7719-09-7 thionyl chloride 
• 822-87-7 2-Chlorocyclohexanone 
• 1666-13-3 diphenyl diselenide 
• 51533-23-4 (+/-)-rel-((1RS,2SR)-2-chlorocyclohexyl)phenylselenide 

Downstream Products

• 110-82-7 cyclohexane 
• 590-66-9 1,1-dimethylcyclohexane 
• 110-83-8 cyclohexene 
• 7647-01-0 hydrogenchloride 
• 930-66-5 1-chlorocyclohexene 

Relevant articles and documents

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THE CIS CHLORINATION OF ALKENES USING SELENIUM REAGENTS

The phenylselenenyl chloride adduct from alkenes can be oxidised and the seleno moiety can be displaced by chloride to give high yields of dichlorides with cis geometry.

A NOVEL ONE-STEP OXIDATION OF TERMINAL EPOXIDES TO ALLYLIC ALDEHYDES

Various gibberellin epoxides have been oxidized with sulphuryl chloride to α,β-unsaturated aldehydes in >70percent isolated yield.This novel one-step oxidation occurs in the presence of hydroxy (except at C-13) ester, lactone and olefinic functions.

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Chlorination of Cyclohexene by Copper(II) Chloride

Evidence is presented which indicates that CuCl+ is the reactive species in the chlorination of cyclohexene by copper(II) chloride in acetonitrile.The reaction is retarded by an excess of chloride ion and by copper(I) salts, and accelerated by aluminium trichloride.A kinetic scheme which accounts for these observations is suggested.

The Electrochemical cis-Chlorination of Alkenes

The first example for the electrochemical cis-dichlorination of alkenes is presented. The reaction can be performed with little experimental effort by using phenylselenyl chloride as catalyst and tetrabutylammoniumchloride as supporting electrolyte, which also acts as nucleophilic reagent for the SN2-type replacement of selenium versus chloride. Cyclic voltammetric measurements and control experiments revealed a dual role of phenylselenyl chloride in the reaction. Based on these results a reaction mechanism was postulated, where the key step of the process is the activation of a phenylselenyl chloride-alkene adduct by electrochemically generated phenylselenyl trichloride. Like this, different aliphatic and aromatic cyclic and acyclic alkenes were converted to the dichlorinated products. Thereby, throughout high diastereoselectivities were achieved for the cis-chlorinated compounds of >95 : 5 or higher.