13618-83-2

Usage

Uses

Used in Organic Synthesis:
1β,4α-Dibromocyclohexane is used as a reagent in organic synthesis for its ability to facilitate the creation of a range of organic compounds. Its unique structure allows for versatile reactions, making it a valuable component in the synthesis process.
Used in Pharmaceutical Preparation:
In the pharmaceutical industry, 1β,4α-Dibromocyclohexane is used as an intermediate in the preparation of various pharmaceuticals. Its role in the synthesis of medicinal compounds highlights its importance in drug development.
Used in Agrochemical Production:
1β,4α-Dibromocyclohexane is also utilized in the production of agrochemicals, contributing to the development of substances used in agriculture to protect crops and enhance yields.
Used in Research Applications:
In research settings, 1β,4α-Dibromocyclohexane is employed for studying chemical reactions and exploring new synthetic pathways, further expanding the understanding of organic chemistry and its applications.

Upstream product

• 279-49-2 7-oxabicyclo(2.2.1)heptane 
• 556-48-9 1,4-Cyclohexanediol 
• 108-85-0 1-bromocyclohexane 
• 186-04-9 cis-bicyclo<2.2.0>hexane 
• 2044-08-8 1-bromocyclohex-1-ene 
• 7705-08-0 iron(III) chloride 
• 32617-36-0 1-bromo-1-chloro-cyclohexane 
• 10035-10-6 hydrogen bromide 
• 10489-97-1 dibromo-cyclohexane 
• 2108-92-1 1,1-dichlrocyclohexane 
• 6939-74-8 optically inactive 1.3-diacetoxy-cyclohexane 
• 106421-17-4 ethyl-cyclohex-3-enyl ether 
• 6289-83-4 trans-1,4-diacetoxy-cyclohexane 
• 930-66-5 1-chlorocyclohexene 

Downstream Products

• 592-42-7 1,5-Hexadien 
• 1165952-91-9 cyclohexa-1,3-diene 
• 110-83-8 cyclohexene 
• 71-43-2 benzene 
• 549520-97-0 cis-2-[4-(4-bromocyclohexyl)-piperazin-1-yl]pyrimidine 
• 822-66-2 3-cyclohexen-1-ol 
• 109470-24-8 [1]naphthyl-carbamic acid cyclohex-3-enyl ester 
• 100372-07-4 phenyl-carbamic acid cyclohex-3-enyl ester 

Relevant academic research and scientific papers

Rigid analogues of buspirone and gepirone, 5-HT1A receptors partial agonists.

Rigid analogues of buspirone and gepirone, 5-HT1A receptors partial agonists, were obtained. The compounds exhibited very low affinity to the receptors. Their structural features resembled to a large extent the arrangement of the respective structural elements found in the solid state of buspirone and in the theoretical structure of NAN-190 (5-HT1A postsynaptic antagonist) rigid analogue exhibiting high affinity to the receptor. The obtained results would thus suggest that the bioactive conformation of buspirone might not be the extended one. That would additionally suggest that either both groups of compounds could occupy different areas at the receptor binding sites (or bind to different receptor states) or the constrained structure of 2 does not represent well 5-HT1A receptor binding site requirements.

The functionalization of saturated hydrocarbons. Part 25. Ionic substitution reactions in GoAggIV chemistry: The formation of carbon-halogen bonds

GoAggIV chemistry (Fe (III) species, tert-butyl hydroperoxide in a mixture of pyridine and acetic acid) in the presence of LiCl can transform saturated hydrocarbons efficiently into the corresponding alkyl chlorides. The transformation into monosubstituted alkyl derivatives by "ionic trapping" reagents arising from the interception of the first intermediate of the system supports the presence of a high valent VFe-C species. Mechanistic studies suggest a possible pathway operating via an Fe-centered ligand coupling. In addition, the production of alkyl chlorides and alkyl bromides could also be achieved employing this system in the presence of halogenating reagents such as CCl4 and BrCCl3.

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.

Studies on the bromination of saturated hydrocarbons under GoAggIII conditions

The bromination reaction of saturated hydrocarbons under GoAggIII conditons (FeCl3.6H2O picolinic acid, H2O2 in pyridine/acetic acid) and under radical chain conditions (dibenzoyl peroxide in pyridine/acetic acid or initiation by UV light) are compared. Differences in the selectivity and kinetic behavior for a series of polyhaloalkanes are in agreement with a non-radical mechanism for GoAggIII bromination. Comparison of the kinetic order of reactivity for a series of polyhaloalkanes under chain radical conditions and under GoAggIII conditions is in agreement with a non-radical reaction pathway for the Gif-type bromination reaction.

Homolytic Rearrangements of Bicyclohexane and Bicycloheptane

Free radicals abstract hydrogen from both the bridge and bridgehead sites in bicyclohexane (4).The bicyclohexan-1-yl radical was observed by e.p.r. spectroscopy.The bicyclohexan-2-yl radical rearranges by stereoelectronically forbidden β-scission to give cyclohex-3-enyl radicals.Unlike other cyclobutanes, compound (4) undergoes an SH2 reaction with bromine atoms.Free radicals abstract hydrogen only from the methylene groups of the C5 ring in bicycloheptane (15a).The bicycloheptan-2-yl radicals were observed by e.p.r. spectroscopy, as was their rearrangement, by stereoelectronically allowed β-scission, to 2-(cyclopent-2-enyl)ethyl radicals.Bromine atoms abstract hydrogen from (15a) and no SH2 reaction was detected.The radicals and their rearrangements were studied by semi-empirical MINDO/3 and MNDO methods.

Radical Rearrangements of Bicyclohexane: Homolytic Substitution of a Cyclobutane Ring

Bromine atoms react with bicyclohexane in an SH2 reaction at the bridgehead carbon atoms; the bicyclohex-2-yl radical rearranges by β-scission of the inter-ring bond.