cis-1,2-Cyclohexanediol
Synthesis- Product Name
- cis-1,2-Cyclohexanediol
- CAS No.
- 1792-81-0
- Chemical Name
- cis-1,2-Cyclohexanediol
- Synonyms
- Grandidentol;TIMTEC-BB SBB007678;CIS-HEXAHYDROCATECHOL;CIS-1,2-CYCLOHEXANEDIOL;Adipic Acid Impurity 29;1,2-cis-cyclohexanediol;cis-Cyclohexane-1,2-diol;cis-2-Hydroxycyclohexanol;1,2-Cyclohexanediol, cis-;(1S)-1α,2α-Cyclohexanediol
- CBNumber
- CB8159715
- Molecular Formula
- C6H12O2
- Formula Weight
- 116.16
- MOL File
- 1792-81-0.mol
cis-1,2-Cyclohexanediol Property
- Melting point:
- 97-101 °C (lit.)
- Boiling point:
- 116 °C / 13mmHg
- Density
- 1.0297
- refractive index
- 1.4270 (estimate)
- solubility
- soluble in Methanol
- form
- Crystalline Flakes or Powder
- pka
- 14.49±0.40(Predicted)
- color
- White to light beige
- Water Solubility
- slightly soluble
- BRN
- 1340578
- CAS DataBase Reference
- 1792-81-0(CAS DataBase Reference)
- NIST Chemistry Reference
- cis-1,2-Cyclohexanediol(1792-81-0)
N-Bromosuccinimide Price
- Product number
- 361267
- Product name
- cis-1,2-Cyclohexanediol
- Purity
- 99%
- Packaging
- 1g
- Price
- $56.3
- Updated
- 2024/03/01
- Product number
- C1802
- Product name
- cis-1,2-Cyclohexanediol
- Purity
- >98.0%(GC)
- Packaging
- 1g
- Price
- $51
- Updated
- 2024/03/01
- Product number
- C997755
- Product name
- cis-1,2-Cyclohexanediol
- Packaging
- 250mg
- Price
- $85
- Updated
- 2021/12/16
- Product number
- FC58748
- Product name
- cis-1,2-Cyclohexanediol
- Packaging
- 1g
- Price
- $90
- Updated
- 2021/12/16
- Product number
- M185
- Product name
- cis-1,2-Cyclohexanediol
- Packaging
- 1g
- Price
- $94
- Updated
- 2021/12/16
cis-1,2-Cyclohexanediol Chemical Properties,Usage,Production
Synthesis
To a mixture of N-methylmorpholine-N-oxide.2H2O (18.2 g, 155 mmol), water (50 mL), acetone (20 mL), and osmium tetroxide (80 mg) in t-butanol (8 mL) was added distilled cyclohexene (10.1 mL, 100 mmol). The reaction was slightly exothermic initially and was maintained at room temperature with a water bath. The reaction was complete after stirring overnight at room temperature under nitrogen. A slurry of 1 g of sodium hydrosulfifite, 12 g of magnesium silicate (magnesol), and 80 ml of water was added, and the magnesol was fifiltered. The fifiltrate was neutralized to pH 7 with 1 N H2SO4, the acetone was evaporated under vacuum, and the pH was further adjusted to pH 2. The solution was saturated with NaCl and extracted with EtOAc. The aqueous phase was concentrated by azeotroping with n-butanol and further extracted with ethyl acetate. The combined ethyl acetate layers were dried and evaporated, yielding 11.2 g (96.6%) of crystalline solid. Recrystallization from ether provided 10.6 g (91%) of cis-1,2-cyclohexanediol, mp 95–97°C.
Reference: Van Rheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 17, 1973−1976.
Chemical Properties
White to light beige crystalline flakes or powder
Uses
cis-1,2-Cyclohexanediol is a reagent used in the synthesis of boronic esters of corannulene which are used to prepare icosahedral supramolecules.
Definition
ChEBI: A cyclohexane-1,2-diol with cis-configuration.
General Description
Core-shell-like silica nickel species nanoparticle catalyzed dehydrogenation of 1,2-cyclohexanediol to catechol is reported. Crystal structure of a Cr(V) complex with cis-1,2-cyclohexanediol is reported. Enzymatic oxidation of cis-1,2-cyclohexanediol by Gluconobacter oxydans (ATCC 621) is reported.