2425-33-4

Basic information

• Product Name: (1S,2R)-2-BROMO-CYCLOHEXANOL
• Synonyms: (1S,2R)-2-BROMO-CYCLOHEXANOL;rel-(1R*)-2α*-Bromocyclohexane-1β*-ol;rel-(1α*)-2β*-Bromocyclohexanol;rel-(1β*)-2α*-Bromocyclohexanol;rel-2β*-Bromo-1α*-cyclohexanol
• CAS NO: 2425-33-4
• Molecular Formula: C₆H₁₁BrO
• Molecular Weight: 179.05494
• Mol File: 2425-33-4.mol
• Article Data: 80

Chemical Properties

• Melting Point: 27 °C
• Boiling Point: 225.5°Cat760mmHg
• Flash Point: 90.2°C
• Appearance: /
• Density: 1.519g/cm³
• Vapor Pressure: 0.0171mmHg at 25°C
• Refractive Index: 1.541
• PKA: 14.30±0.40(Predicted)
• CAS DataBase Reference: (1S,2R)-2-BROMO-CYCLOHEXANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-2-BROMO-CYCLOHEXANOL(2425-33-4)
• EPA Substance Registry System: (1S,2R)-2-BROMO-CYCLOHEXANOL(2425-33-4)

Safety Data

• Hazardous Substances Data: 2425-33-4(Hazardous Substances Data)

Usage

General Description

(1S,2R)-2-Bromo-cyclohexanol is a chemical compound with the molecular formula C6H11BrO. It is a chiral organobromine compound with a bicyclic structure. (1S,2R)-2-BROMO-CYCLOHEXANOL is a colorless liquid at room temperature and is commonly used as a reagent in organic synthesis. The (1S,2R)-2-Bromo-cyclohexanol has applications in the pharmaceutical and agrochemical industries, where it is used as an intermediate in the production of various substances. Its chiral nature and cyclohexane ring make it a versatile building block for the synthesis of complex organic molecules.

InChI:InChI=1/C6H11BrO/c7-5-3-1-2-4-6(5)8/h5-6,8H,1-4H2

Upstream product

• 1611-82-1 tert-butyl hypobromite 
• 110-83-8 cyclohexene 
• 357-57-3 brucine 
• 56-23-5 tetrachloromethane 
• 2425-33-4 2-bromocyclocyclohexanol 
• 108-24-7 acetic anhydride 
• 286-20-4 cyclohexane-1,2-epoxide 
• 420-04-2 CYANAMID 
• 34701-03-6 trans-1-bromo-2-iodocyclohexane 
• 1826-67-1 vinyl magnesium bromide 
• 927-77-5 n-propylmagnesium bromide 
• 286-20-4 cyclohexene oxide 
• 35446-84-5 trans-2-(phenylseleno)cyclohexanol 
• 2955-74-0 ethyl N-{[(4-nitrobenzene)sulfonyl]oxy}carbamate 

Downstream Products

• 2425-33-4 (-)-trans-2-bromo-cyclohexanol-⁽¹⁾ 
• 5837-71-8 (-)-trans-2-bromo-1-acetoxy-cyclohexane 
• 62921-46-4 trans-2-acetoxy-1-cyclohexanol 
• 1759-71-3 trans-1,2-cyclohexanediol diacetate 
• 53023-25-9 trans-2-bromocyclohexan-1-ol 
• 5401-62-7 1,2-dibromocyclohexane 
• 931-16-8 (+/-)-trans-2-aminocyclohexanol 
• 13898-96-9 (+-)-trans-1-bromo-2-chloro-cyclohexane 
• 7429-37-0 trans-1,2-dibromocyclohexane 
• 108595-93-3 (+/-)-nitrous acid-(trans-2-bromo-cyclohexyl ester) 
• 16886-68-3 trans-2-bromocyclohexyl nitrate 
• 106320-25-6 (+/-)-trans-3,5-dinitrobenzoic acid 2-bromocyclohexyl ester 
• 16886-68-3 (+/-)-cis-1-bromo-2-nitryloxy-cyclohexane 
• 5837-71-8 trans-1-acetoxy-2-bromocyclohexane 

Relevant articles and documents

Electrochemical bromofunctionalization of alkenes in a flow reactor

The bromination of organic molecules has been extensively studied to date, yet there is still a demand for safe and sustainable methodologies. Hazardous reagents, selectivity, low atom economy and waste production are the most persisting problems of brominating reagents. The electrochemical oxidation of bromide to bromine is a viable strategy to reduce waste by avoiding chemical oxidants. Furthermore, thein situgeneration of reactive intermediates minimizes the risk of hazardous reagents. In this work, we investigate the electrochemical generation of bromine from hydrobromic acid in a flow electrochemical reactor. Various alkenes could be converted to their corresponding dibromides, bromohydrines, bromohydrin ethers and cyclized products in good to excellent yields.

Catalytic Asymmetric Bromination of Unfunctionalized Olefins with H2O as a Nucleophile

The dimeric cinchona alkaloid (DHQD)2PHAL is used to catalyze an effective asymmetric bromohydroxylation of unfunctionalized olefins with H2O as nucleophile an N-bromobenzamide as a bromine source. A variety of optically active bromohydrins are formed with up to 88%ee. PHAL's positive: An effective asymmetric bromohydroxylation of unfunctionalized olefins with H2O as nucleophile catalyzed by the dimeric cinchona alkaloid (DHQD)2PHAL (see scheme) is described. Optically active bromohydrins are obtained with up to 88%ee.

Synthesis of Di-, Tri-, and tetrasubstituted oxetanes by rhodium-catalyzed O-H insertion and C-C bond-forming cyclization

Oxetanes offer exciting potential as structural motifs and intermediates in drug discovery and materials science. Here an efficient strategy for the synthesis of oxetane rings incorporating pendant functional groups is described. A wide variety of oxetane 2,2-dicarboxylates were accessed in high yields, including functionalized 3-/4-aryl-and alkyl-substituted oxetanes and fused oxetane bicycles. Enantioenriched alcohols provided enantioenriched oxetanes with complete retention of configuration. The oxetane products were further derivatized, while the ring was maintained intact, thus highlighting their potential as building blocks for medicinal chemistry.