931-13-5

Basic information

• Product Name: (1R,2R)-2-chlorocyclohexanol
• Synonyms: (1R,2R)-2-chlorocyclohexanol
• CAS NO: 931-13-5
• Molecular Weight: 134.606
• Mol File: 931-13-5.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: (1R,2R)-2-chlorocyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-2-chlorocyclohexanol(931-13-5)
• EPA Substance Registry System: (1R,2R)-2-chlorocyclohexanol(931-13-5)

Safety Data

• Hazardous Substances Data: 931-13-5(Hazardous Substances Data)

Upstream product

• 286-20-4 cyclohexane-1,2-epoxide 
• 141-78-6 ethyl acetate 
• 154726-22-4 (1R,2R)-2-chlorocyclohexyl acetate 
• 1561-86-0 2-chlorocyclohexanol 
• 822-87-7 2-Chlorocyclohexanone 
• 33815-66-6 C₈H₁₃ClO₂ 
• 116783-28-9 cis-2-chlorocyclohexanol 
• 286-20-4 cyclohexene oxide 
• 134070-91-0 2-chlorocyclohexylbutyrate 
• 6628-80-4 trans-2-chlorocyclohexanol 
• 85116-37-6 (-)-diisopinocamphenylborane chloride 
• 78-84-2 isobutyraldehyde 
• 123-38-6 propionaldehyde 

Downstream Products

• 66530-13-0 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2S)-2-chloro-cyclohexyl ester 
• 66574-30-9 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2R)-2-chloro-cyclohexyl ester 
• 937207-26-6 (1R,2R)-2-(4-methylphenylamino)cyclohexane-1-ol 

Relevant articles and documents

A phosphonium ylide as a visible light organophotoredox catalyst

A phosphonium ylide-based visible light organophotoredox catalyst has been designed and successfully applied to halohydrin synthesis using trichloroacetonitrile and epoxides. An oxidative quenching cycle by the ylide catalyst was established, which was confirmed by experimental mechanistic studies.

Conformationally rigid chiral bicyclic skeleton-tethered bipyridine N,N'-dioxide as organocatalyst: Asymmetric ring opening of meso-epoxides

The conformationally rigid chiral bicyclic skeleton tethered bipyridine NN'-dioxide (-)-9 has been designed, synthesized and examined as an organocatalyst in the enantioselective ring opening of meso-epoxides using tetrachlorosilane (SiCl4). The catalyst (-)-9 is found to exhibit good enantioselectivity for substituted cis-stilbene epoxides; whereas, the saturated cyclic meso-epoxides display a moderate enantioselectivity. At -30 °C in chloroform, the catalyst (-)-9 with 0.5 mol % loading generated the chlorohydrins in up to 97 % yield with up to 93 % ee. The possible creation of transient axial chiral environment around hypervalent silicon species due to the presence of conformationally rigid chiral bicyclic skeleton tethered bipyridine N,N'-dioxide may be responsible for such enantioselectivity observed in the desymmetrization of meso-epoxides.

Facile synthesis of chiral 1,2-chlorohydrins via the ring-opening of meso-epoxides catalyzed by chiral phosphine oxides

The facile synthesis of chiral 1,2-chlorohydrins via the enantioselective ring-opening of meso-epoxides with silicon tetrachloride in the presence of a chiral phosphine oxide was accomplished. The chiral 1,2-chlorohydrins were also obtained from the corresponding cis-alkenes in one-pot without significant loss in the selectivity, thereby permitting easy access to the 1,2-chlorohydrins from cis-alkenes with good yields and enantioselectivities.