19246-38-9

Basic information

• Product Name: 1α,2α-Dibromocyclohexane
• Synonyms: (1R,2S)-1,2-Dibromocyclohexane;Cyclohexane, 1,2-dibromo-, cis-
• CAS NO: 19246-38-9
• Molecular Formula: C₆H₁₀Br₂
• Molecular Weight: 241.9516
• Mol File: 19246-38-9.mol

Chemical Properties

• Melting Point: 9.7°C
• Boiling Point: 204.74°C (rough estimate)
• Flash Point: 91.5°C
• Appearance: /
• Density: 1.7980
• Refractive Index: 1.5514 (estimate)
• CAS DataBase Reference: 1α,2α-Dibromocyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: 1α,2α-Dibromocyclohexane(19246-38-9)
• EPA Substance Registry System: 1α,2α-Dibromocyclohexane(19246-38-9)

Safety Data

• Hazardous Substances Data: 19246-38-9(Hazardous Substances Data)

Upstream product

• 2044-08-8 1-bromocyclohex-1-ene 
• 10035-10-6 hydrogen bromide 
• 7705-08-0 iron(III) chloride 
• 930-66-5 1-chlorocyclohexene 
• 110-83-8 cyclohexene 
• 67-56-1 methanol 
• 108-85-0 1-bromocyclohexane 

Downstream Products

• 28907-20-2 cis-cyclohexane-1,2-dicarbonitrile 
• 2044-08-8 1-bromocyclohex-1-ene 
• 7726-95-6 bromine 
• 110-83-8 cyclohexene 

Relevant articles and documents

Organocatalytic diastereoselective dibromination of alkenes

A highly diastereoselective pyrrolidine-promoted dibromination of alkenes by combination of NBS and succinimide is presented. The pyrrolidine-mediated dibromination of alkenes is higly anti-selective and gives the corresponding products in moderate to high yields and up to >25:1 dr.

Comparative study of the vicinal functionalization of olefins with 2:1 bromide/bromate and iodide/iodate reagents

A comparative evaluation was made on the syntheses of vicinal halohydrins, halo methyl ethers, and halo acetates from olefins using 2:1 Br-/BrO3- and I-/IO3- reagents. In many cases both reagents afforded products selectively in high yields. The highest halogen atom efficiencies attained were 97% and 93% for Br-/BrO3- and I-/IO3-, respectively. Of the two reagents, I-/IO3- was established to be the preferred reagent for vicinal functionalization of linear alkenes and also for halo acetate preparation. However, only Br-/BrO3- was effective for vicinal functionalization of trans-stilbene and chalcones.

The functionalization of saturated hydrocarbons. Part 23. Gif-type bromination and chlorination of saturated hydrocarbons: A non-radical reaction

The bromination of saturated hydrocarbons was studied in the GoAggIII system using CBrCl3 and other polyhaloalkanes. This bromination reaction was compared to free radical processes by (i) evaluating the rates of reactions for a series of polyhaloalkanes, by (ii) measuring the selectivity of the different systems towards various saturated hydrocarbons and by (iii) analyzing the product distribution arising from the bromination of cyclohexyl bromide under both the GoAggIII type conditions and from known processes for alkyl radical generation. Some chlorine containing reagents were also examined for C - Cl bond formation in the GoAggIII system. All the experimental findings support a mechanism for the reaction that is different from one involving free radicals. This non-radical pathway is common in all Gif-type systems, as seen in common patterns of selectivity, conditions is in agreement with a non-radical reaction pathway for the Gif-type bromination and chlorination reactions.

Halogenobis(N,N-dialkyldithiocarbamato)iron(III) Complexes as Potential Catalysts for Halogen Addition Reactions to Alkenes

In the presence of a catalytic amount of iron(III) halogenobisdithiocarbamates, the addition of molecular halogens to alkenes occurs rapidly to afford cis-addition products.