cis-1,2-Dihydrocatechol
| Names | |
|---|---|
| IUPAC name
3,5-Cyclohexadiene-1,2-diol
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChEBI | |
| ChemSpider | |
| 200913 | |
| KEGG | |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C6H8O2 | |
| Molar mass | 112.128 g·mol−1 |
| Appearance | white oily solid |
| Melting point | 28 °C (82 °F; 301 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
| |
cis-1,2-Dihydrocatechol is the organic compound with the formula C6H6(OH)2. Several isomers exist with this formula. It is a colorless solid melting near room temperature. The compound is classified as a 1,3-cyclohexadiene. It arises by the dihydroxylation of benzene catalyzed by toluene dioxygenase. It can also be prepared from catechol using the enzyme cis-1,2-dihydrobenzene-1,2-diol dehydrogenase:[1][2]
cis-1,2-Dihydrocatechol has been used in the synthesis, sometimes on a commercial scale, of indinavir, indigo, and poly(p-phenylene).[3]
References
- ^ Axcell BC, Geary PJ (1973). "The metabolism of benzene by bacteria. Purification and some properties of the enzyme cis-1,2-dihydroxycyclohexa-3,5-diene (nicotinamide adenine dinucleotide) oxidoreductase (cis-benzene glycol dehydrogenase)". Biochem. J. 136 (4): 927–34. doi:10.1042/bj1360927. PMC 1166042. PMID 4362337.
- ^ Gibson DT, Koch JR, Kallio RE (1968). "Oxidative degradation of aromatic hydrocarbons by microorganisms. I Enzymatic formation of catechol from benzene". Biochemistry. 7 (7): 2653–62. doi:10.1021/bi00847a031. PMID 4298226.
- ^ Hudlicky, Tomas; Thorpe, Andrew J. (1996). "Current Status and Future Perspectives of Cyclohexadiene-cis-diols in Organic Synthesis: Versatile Intermediates in the Concise Design of Natural Products". Chemical Communications (17): 1993. doi:10.1039/cc9960001993.