130792-45-9

Basic information

• Product Name: (1S-CIS)-3-BROMO-3,5-CYCLOHEXADIENE-1,2-DIOL
• Synonyms: CIS-(1S,2S)-3-BROMO-3,5,CYCLOHEXADIENE-1,2- DIOL;(+)-CIS-2(S),3(S)-2,3-DIHYDROXY-2,3-DIHYDROBROMOBENZENE;(1S-CIS)-3-BROMO-3,5-CYCLOHEXADIENE-1,2-DIOL;(1S-cis)-3-Bromo-3,5-cyclohexadiene-1,2-diol 0.2 g/mL in 0.1 M phosphate buffer, 96%;(1S,2S)-3-Bromocyclohexa-3,5-diene-1,2-diol (0.2 g/mL in 0.1 M phosphate buffer, 96%)
• CAS NO: 130792-45-9
• Molecular Formula: C₆H₇BrO₂
• Molecular Weight: 191.02
• Mol File: 130792-45-9.mol
• Article Data: 30

Chemical Properties

• Melting Point: 90-94 °C(lit.)
• Boiling Point: 302.342 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.922 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.687
• Storage Temp.: ?20°C
• CAS DataBase Reference: (1S-CIS)-3-BROMO-3,5-CYCLOHEXADIENE-1,2-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (1S-CIS)-3-BROMO-3,5-CYCLOHEXADIENE-1,2-DIOL(130792-45-9)
• EPA Substance Registry System: (1S-CIS)-3-BROMO-3,5-CYCLOHEXADIENE-1,2-DIOL(130792-45-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 130792-45-9(Hazardous Substances Data)

Usage

Description

(1S-cis)-3-Bromo-3,5-cyclohexadiene-1,2-diol is a chiral cis-dienediol that serves as a crucial building block in the synthesis of various natural products. It is characterized by its ability to participate in several chemical reactions, including cycloadditions, sigmatropic rearrangements, electrophilic additions, and oxidative cleavage, which makes it a versatile compound in organic chemistry.

Uses

Used in Pharmaceutical Industry:
(1S-cis)-3-Bromo-3,5-cyclohexadiene-1,2-diol is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique chemical properties and reactivity allow it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, (1S-cis)-3-Bromo-3,5-cyclohexadiene-1,2-diol is utilized as a versatile building block for creating a wide range of complex organic molecules. Its ability to undergo multiple types of chemical reactions makes it a valuable asset in the synthesis of natural products and other specialty chemicals.
Used in Research and Development:
(1S-cis)-3-Bromo-3,5-cyclohexadiene-1,2-diol is also used in research and development settings, where it can be employed to study various chemical reactions and mechanisms. Its unique properties make it an interesting subject for exploring new reaction pathways and developing innovative synthetic methods.
Used in Material Science:
In material science, (1S-cis)-3-Bromo-3,5-cyclohexadiene-1,2-diol may be used as a component in the development of novel materials with specific properties. Its reactivity and structural characteristics can contribute to the creation of advanced materials for various applications, such as in electronics, coatings, or adhesives.

InChI:InChI=1/C6H7BrO2/c7-4-2-1-3-5(8)6(4)9/h1-3,5-6,8-9H/t5-,6+/m0/s1

Upstream product

• 108-86-1 bromobenzene 

Downstream Products

• 114763-28-9 (1S,2R)-1,2-dihydroxy-3-vinylcyclohexa-3,5-diene 
• 138769-97-8 (1S,2S)-1,2-dihydroxy-3-methylsulfanylcyclohexa-3,5-diene 
• 140210-12-4 (1S,2R)-3-Phenylethynyl-cyclohexa-3,5-diene-1,2-diol 
• 137501-12-3 (3aS,4R,5R,7aS)-7-bromo-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxole-4,5-diol 
• 140210-13-5 (1S,2R)-3-Hex-1-ynyl-cyclohexa-3,5-diene-1,2-diol 
• 138769-95-6 (1S,2R)-3-Trimethylsilanylethynyl-cyclohexa-3,5-diene-1,2-diol 
• 173381-12-9 (1S,2S)-1,2-di-tert-butyldimethylsiloxy-3-bromocyclohexa-3,5-diene 
• 173381-13-0 (5S,6S)-1-bromo-5,6-bis(2'-trimethylsilylethoxymethoxy)cyclohexa-1,3-diene 
• 154097-67-3 (1S,2S,3S,4S)-5-bromo-5-cyclohexene-1,2,3,4-tetraol 
• 154013-20-4 (1R,2R,3S,4S)-5-bromo-5-cyclohexene-1,2,3,4-tetraol 
• 174817-06-2 cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohex-3-ene 
• 14381-51-2 3-bromo-1,2-dihydroxybenzene 
• 166191-21-5 (1S,7S,10S,11S)-1-Bromo-10,11-dihydroxy-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-ene-3,5-dione 
• 219655-88-6 (1S,6S)-2-Bromo-6-triisopropylsilanyloxy-cyclohexa-2,4-dienol 

Relevant articles and documents

Aza and oxo Diels-Alder reactions using cis-cyclohexadienediols of microbial origin: Chemoenzymatic preparation of synthetically valuable heterocyclic scaffolds

Aza and oxo Diels-Alder reactions using enantiopure cis-cyclohexadienediols were studied. These dienediols were obtained from the biotransformation of monosubstituted arenes using bacterial dioxygenases (toluene and benzoate dioxygenases). Ethyl glyoxylate and its N-tosyl imine were used as dienophiles to afford the corresponding hetero Diels-Alder bicyclic adducts with excellent regio- and stereoselectivities. Quantum chemical calculations at the B3LYP/6-31+G(d,p) level of theory were performed to rationalize the observed selectivities especially the stereochemical aspects of the cycloadditions. The synthetic importance of these adducts is highlighted for the preparation of enantiopure 2,2,3,4,5,6-hexasubstituted piperidine and tetrahydropyran from toluene.

Synthesis and biological evaluation of 10-benzyloxy-Narciclasine

A chemoenzymatic convergent synthesis of 10-benzyloxy narciclasine from bromobenzene was accomplished in 16 steps. The key transformations included toluene dioxygenase-mediated hydroxylation, nitroso Diels-Alder reaction and intramolecular Heck cyclization. The unnatural derivative of narciclasine was subjected to biological evaluation and its activity was compared to other C-10 and C-7 compounds prepared previously.

Site-Directed Mutagenesis Studies on the Toluene Dioxygenase Enzymatic System: Role of Phenylalanine 366, Threonine 365 and Isoleucine 324 in the Chemo-, Regio-, and Stereoselectivity

Toluene Dioxygenase (TDO) enzymatic complex has been widely used as a biocatalyst for the regio- and enantioselective preparation of cis-cyclohexadienediols, which are very important starting materials for organic synthesis. However, the lack of regio- and stereodiversity of the dioxygenation process by TDO and related dioxygenases constitutes a clear drawback when planning the use of these diols in synthetic schemes. In this work, we developed three TDO mutants in residues phenylalanine 366, threonine 365 and isoleucine 324, with the aim to alter the chemo-, regio- and stereoselectivity of the biotransformation of arenes. While no changes in the regioselectivity of the process were observed, dramatic variations in the chemo- and enantioselectivity were found for mutants I324F, T365N and F366 V in a substrate-dependent manner. (Figure presented.).