80126-17-6

Basic information

• Product Name: 3-bromo-1,2-epoxycyclohexane
• Synonyms: 3-bromo-1,2-epoxycyclohexane
• CAS NO: 80126-17-6
• Molecular Formula: C6H9BrO
• Molecular Weight: 177.0391
• Mol File: 80126-17-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 202.8°Cat760mmHg
• Flash Point: 79.7°C
• Appearance: /
• Density: 1.6g/cm³
• Vapor Pressure: 0.409mmHg at 25°C
• Refractive Index: 1.547
• CAS DataBase Reference: 3-bromo-1,2-epoxycyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-bromo-1,2-epoxycyclohexane(80126-17-6)
• EPA Substance Registry System: 3-bromo-1,2-epoxycyclohexane(80126-17-6)

Safety Data

• Hazardous Substances Data: 80126-17-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H9BrO/c7-4-2-1-3-5-6(4)8-5/h4-6H,1-3H2/t4-,5-,6+/m1/s1

Upstream product

• 56421-05-7 (+/-)-cis-3-bromo-1,2-epoxycyclohexane 

Relevant articles and documents

EANTIOSELECTIVITY OF THE MICROSOMAL EPOXIDE HYDROLASE: HYDROLYSIS OF (+/-)-CIS-3-BROMO-1,2-EPOXYCYCLOHEXANE

The acid-catalysed and the rabbit microsomal epoxide hydrolasa-catalysed hydrolysis of (+/-)-cis-3-bromo-1,2-epoxycyclohexane (1) have been investigated.Both reactions were completely regio- and stereo-specific, giving t-3-bromocyclohexane-r-1,t-2-diol (2) as the only product.Epoxide (1) was found to be a much better substrate for the epoxide hydrolase than its trans-diastereoisomer.Under enzyme saturation conditions the hydrolysis was fairly eneantioselective, as shown both by the biphasic shape of its kinetic profile and by the isolaton of optically active (-)-(1R,2R,3S)-(1) and (-)-(1R,2S,3R)-(2) at incomplete reaction.The absolute configurations have been deduced by correlation with (-)-(R,R)-trans-cyclohexane-1,2-diol.At about 30percent conversion, the enantiomeric excesses of unchanged (1) and formed (2) were 24-30percent and 56-60percent, respectively, and racemic (2) was obtained after complete hydrolysis.The results have been rationalized by a competitive inhibition of (+)-(1S,2S,3R)-(1) on the hydrolysis of (-)-(1) and fit the previously proposed picture describing the substrate enantioselection carried out by the microsomal epoxide hydrolase.