69945-44-4

Basic information

• Product Name: (1RS,2SR,3RS,4RS)-2,3-dibromocyclohex-5-ene-1,4-diol
• CAS NO: 69945-44-4
• Molecular Weight: 271.936
• Mol File: 69945-44-4.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: (1RS,2SR,3RS,4RS)-2,3-dibromocyclohex-5-ene-1,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1RS,2SR,3RS,4RS)-2,3-dibromocyclohex-5-ene-1,4-diol(69945-44-4)
• EPA Substance Registry System: (1RS,2SR,3RS,4RS)-2,3-dibromocyclohex-5-ene-1,4-diol(69945-44-4)

Safety Data

• Hazardous Substances Data: 69945-44-4(Hazardous Substances Data)

Usage

Description

(1RS,2SR,3RS,4RS)-2,3-dibromocyclohex-5-ene-1,4-diol is an organic compound with the molecular formula C6H8Br2O2. It features a cyclohexene ring with two bromine atoms and hydroxyl groups at the 1 and 4 positions, making it a cyclic compound with potential applications in various chemical processes.

Uses

Used in Organic Synthesis:
(1RS,2SR,3RS,4RS)-2,3-dibromocyclohex-5-ene-1,4-diol is used as a key intermediate in organic synthesis for the preparation of other organic compounds. Its unique structure with bromine atoms and hydroxyl groups allows for versatile reactions and the formation of a wide range of products.
Used in Chemical Reactions as a Reagent:
In the field of chemical reactions, (1RS,2SR,3RS,4RS)-2,3-dibromocyclohex-5-ene-1,4-diol serves as a reagent, facilitating various organic transformations. Its presence can enhance the efficiency and selectivity of certain reactions, making it a valuable tool in chemical research and development.
Used in the Study of Organic Chemical Reactions:
(1RS,2SR,3RS,4RS)-2,3-dibromocyclohex-5-ene-1,4-diol is also utilized in academic and research settings to study the mechanisms and kinetics of organic chemical reactions. Its distinct structure provides insights into reaction pathways and helps in understanding the behavior of similar compounds.
It is crucial to handle (1RS,2SR,3RS,4RS)-2,3-dibromocyclohex-5-ene-1,4-diol with care, as it may pose hazards if not used properly, highlighting the importance of safety precautions in its applications.

Upstream product

• 106-51-4 p-benzoquinone 
• 5273-61-0 (5RS,6RS)-5,6-dibromocyclohex-2-ene-1,4-dione 

Downstream Products

• 4381-96-8 (+/-)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol 
• 5273-61-0 trans-5,6-Dibrom-cyclohex-2-en-1,4-dion 
• 18376-35-7 (1α,2β,3α,4β,5β,6β)-1,2-dibromo-3,4,5,6-tetraacetoxycyclo-hexane 
• 18376-35-7 (1α,2β,3α,4α,5β,6β)-1,2-dibromo-3,4,5,6-tetraacetoxycyclohexane 
• 145047-67-2 Acetic acid (1R,2S,3S,4R,5S,6R)-4-acetoxy-2,3-dibromo-5,6-dihydroxy-cyclohexyl ester 
• 18376-36-8 (1S,2S,3S,4S,5R,6R)-5,6-Dibromo-cyclohexane-1,2,3,4-tetraol 
• 4381-96-8 (+/-)-tetraacetylconduritol C 
• 4381-96-8 (+/-)-1,2,3,4-tetra-O-acetylconduritol E 
• 526-87-4 (+/-)-conduritol C 
• 526-87-4 conduritol-E 
• 222420-83-9 D-myo-3,6-bis-O-(di-O-benzylphospho)-4,5-bis-O-(2-oxo-5,6-benzo-1,3,2-dioxaphosphep-2-yl)inositol 
• 864372-82-7 (1S,2S,3S,4S)-1,4-bis-O-(di-O-benzylphospho)-2,3-bis-O-(2-oxo-5,6-benzo-1,3,2-dioxaphosphep-2-yl)conduritol-B 
• 222420-77-1 (1S,2R,3R,4S)-1,4-bis-O-(di-O-benzylphospho)conduritol B 
• 1311140-98-3 Inositol 1,5,6-triphosphate 

Relevant articles and documents

Highly Functionalized Cyclohexenyl Systems: Enzymatic Resolution and Selective Oxirane Opening Reactions of p-Benzoquinone Derivatives

Diol 2, derived in two steps from p-benzoquinone, was converted to epoxy alcohol 3. The latter was resolved with crude Candida rugosa lipase in isopropenyl acetate/toluene to give acetate (-)-4 and residual alcohol (+)-3. Oxirane ring opening reactions of 3 and the corresponding acetate and TBDMS derivatives with a variety of nucleophiles gave diastereomerically pure 3,4,5,6-tetrasubstituted cyclohexene derivatives of type 6. X-ray crystal structures were obtained on compounds 6e, 6m and the diacetate prepared from 61. Nitrogen nucleophiles provided entry in various aziridines 10. Pd(0)-catalyzed nucleophilic additions to substrate 5 cleanly provided the diastereomeric pattern of type 11. trans-5,6-Disubstituted cyclohexadienes 13 were obtained by an unusual syn-reductive elimination on bromocarbonates 12 utilizing Pd or Zn.

Regio- and stereospecific synthesis of DL-4,5-dibromo-4,5-dideoxy-3,6-O-methyl-chiro-inositol

The regio- and stereospecific synthesis of DL-4,5-dibromo-4,5-dideoxy-3,6-O-methyl-chiro-inositol is reported. Bromination of p-benzoquinone followed by reduction of the carbonyl groups with NaBH4 gave the corresponding trans-dibromodiol compou

Synthesis of novel cyano-cyclitols and their stereoselective biotransformation catalyzed by Rhodococcus erythropolis A4

A variety of novel cyano-cyclitols possessing complex stereochemistry have been synthesized. These compounds were subjected to the biocatalyzed hydrolysis of their nitrile groups. The bacterial strain Rhodococcus erythropolis A4, expressing a nitrile hydr