1521-51-3

Basic information

• Product Name: 3-BROMOCYCLOHEXENE
• Synonyms: 1-Bromo-2-cyclohexene;2-Cyclohexenyl bromide;3-Bromo-1-cyclohexene;1,2,3,4-TETRAHYDROBROMOBENZENE;2-CYCLOHEXEN-1-YL BROMIDE;(+/-)-3-BROMOCYCLOHEXENE;3-BROMOCYCLOHEXENE;TIMTEC-BB SBB007864
• CAS NO: 1521-51-3
• Molecular Formula: C₆H₉Br
• Molecular Weight: 161.04
• Mol File: 1521-51-3.mol
• Article Data: 55

Chemical Properties

• Melting Point: 131-134 °C
• Boiling Point: 57-58 °C12 mm Hg(lit.)
• Flash Point: 130 °F
• Appearance: White to off-white/Solid
• Density: 1.4 g/mL at 25 °C(lit.)
• Vapor Pressure: 5.49mmHg at 25°C
• Refractive Index: n20/D 1.528(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Not miscible or difficult to mix in water.
• BRN: 635953
• CAS DataBase Reference: 3-BROMOCYCLOHEXENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMOCYCLOHEXENE(1521-51-3)
• EPA Substance Registry System: 3-BROMOCYCLOHEXENE(1521-51-3)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 1521-51-3(Hazardous Substances Data)

Usage

Description

3-Bromocyclohexene is a clear colorless to yellow liquid that serves as an important intermediate in the synthesis of various organic compounds. It is a brominated hydrocarbon with a cyclohexene ring, which provides it with unique chemical properties that make it useful in a range of applications.

Uses

Used in Pharmaceutical Synthesis:
3-Bromocyclohexene is used as a synthetic intermediate for the production of N-tert-butoxycarbonyl-O-cyclohexyl-L-tyrosine, a compound with potential pharmaceutical applications. Its unique structure allows for the creation of complex molecules that can be used in the development of new drugs.
Used in Chiral Compound Synthesis:
In the field of chiral chemistry, 3-bromocyclohexene is used as a key building block for the synthesis of enantiopure cyclohexitols such as muco-quercitol, D-chiro-inocitol, and allo-inocitol. These cyclohexitols have various applications in the pharmaceutical and chemical industries, including the development of drugs with improved efficacy and reduced side effects.
Used in Chemical Research:
3-Bromocyclohexene's unique chemical properties make it a valuable compound for research purposes. It can be used to study the reactivity of brominated hydrocarbons and their interactions with other molecules, contributing to the advancement of chemical knowledge and the development of new synthetic methods.
Used in Material Science:
The properties of 3-bromocyclohexene can also be exploited in the development of new materials with specific characteristics, such as improved stability or reactivity. Its use in material science can lead to the creation of novel materials with applications in various industries, including electronics, coatings, and adhesives.

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 3863, 1985 DOI: 10.1016/S0040-4039(00)89271-0

InChI:InChI=1/C6H9Br/c7-6-4-2-1-3-5-6/h2,4,6H,1,3,5H2/t6-/m1/s1

Upstream product

• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 110-83-8 cyclohexene 
• 3699-18-1 N-bromoglutarimide 
• 7072-23-3 1,3-dibromo-5,5-dimethyl-hydantoin 
• 2439-85-2 N-bromophthalimide 
• 822-67-3 Cyclohex-2-enol 
• 77-48-5 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione 
• 5401-62-7 1,2-dibromocyclohexane 
• 1165952-92-0 cyclohexa-1,4-diene 
• 1165952-91-9 cyclohexa-1,3-diene 
• 20244-61-5 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one 
• 426-46-0 pentafluoro-propionic acid bromoamide 
• 79-15-2 N-bromoacetamide 

Downstream Products

• 61862-37-1 (2-cyclohexen-1-yl)piperidine 
• 853920-96-4 cyclohex-2-enyl-[2]thienyl-acetonitrile 
• 107055-43-6 2-cyclohex-2-enyl-1,2,3,4-tetrahydro-isoquinoline 
• 58008-22-3 2-cyclohex-2-enyl-cyclohexane-1,3-dione 
• 5558-37-2 2-(cyclohex-2-en-1-yl)-2-phenylacetonitrile 
• 76644-52-5 rac-3-acetoxycyclohexene 
• 99853-77-7 6-chloro-7-cyclohex-2-enyl-7H-purine 
• 91066-65-8 (+/-)-9-(2-cyclohexen-1-yl)-6-chloropurine 
• 66950-33-2 N,N-dimethylamino-1-cyclohex-2-ene 
• 100056-79-9 2-(2-Cyclohexen-1-yl)-1-cyclopentanon 
• 52034-22-7 3-anilinocyclohexene 
• 115125-55-8 3-(p-tolylthio)cyclohexene 
• 40141-09-1 3-(4-methoxyphenyl)cyclohexene 
• 3983-07-1 3-n-butylcyclohexene 

Relevant articles and documents

Gold-Catalyzed Formal Hexadehydro-Diels-Alder/Carboalkoxylation Reaction Cascades

A dual gold-catalyzed hexadehydro-Diels-Alder/carboalkoxylation cascade reaction is reported. In this transformation, the gold catalyst participated in the hexadehydro-Diels-Alder step, switching the mechanism from a radical type to a cationic one, and then the catalyst activated the resulting aryne to form an ortho-Au phenyl cation species, which underwent a carboalkoxylation rearrangement rather than the expected aryne-ene reaction.

A lutidine-promoted photoredox catalytic atom-transfer radical cyclization reaction for the synthesis of 4-bromo-3,3-dialkyl-octahydro-indol-2-ones

Reported herein is a visible-light-catalyzed photoredox atom-transfer radical cyclization (ATRC) halo-alkylation of 1,6-dienes with α-halo-ketones as the ATRC reagent. This process exhibits high atom economy, high step economy, and high redox economy, which can directly construct a 4-bromo-3,3-dialkyl-octahydro-indol-2-one core under mild conditions in one pot, and lutidine is found to be the key promoter for this ATRC process.

Synthesis of pentacyclic compounds via intramolecular [3 + 2] photocycloaddition of cycloalkene linked naphthalenes

Intramolecular photocycloaddition reactions of cycloalkene linked naphthalenes lead to formation of pentacyclic compounds in a high yielding and stereoselective manner. Intramolecular [2 + 2] cycloadducts are formed initially in photoreactions of cycloalkene linked 1-cyanonaphthalenes. The initially formed intramolecular [2 + 2] cycloadducts absorb light at wavelengths used to promote the photochemical reactions and, as a result, they undergo efficient photocycloreversion to regenerate the starting substrates. In a less efficient competing process, the cycloalkene linked 1-cyanonaphthalenes react to form [3 + 2] intramolecular photoadducts, which do not absorb incident light under the conditions used. Consequently, these photoadducts become the major products in these processes. The relative configuration of the major diastereomers of the pentacyclic products formed from photoreactions of cyclopentene linked naphthalenes (cis-cis) differ from those (cis-trans) arising from the cyclooctene linked substrates. The results of theoretical calculations, which show that steric factors govern the preferred facial mode of intramolecular addition, are in good agreement with the stereochemical course of these photoreactions.