823-18-7

Basic information

• Product Name: cyclohexane-1,3-diol
• Synonyms: (1R)-1β,3β-Dihydroxycyclohexane;(1R)-Cyclohexane-1β,3β-diol;(1R,3S)-1,3-Cyclohexanediol;cis-1,3-Dihydroxycyclohexane;cis-1,3-Cyclohexanediol
• CAS NO: 823-18-7
• Molecular Formula: C₆H₁₂O₂
• Molecular Weight: 116.16008
• Mol File: 823-18-7.mol
• Article Data: 13

Chemical Properties

• Melting Point: 81.0 to 85.0 °C
• Boiling Point: 125°C/5mmHg(lit.)
• Flash Point: 123.9 °C
• Appearance: /
• Density: 0.9958 (rough estimate)
• Refractive Index: 1.4340 (estimate)
• CAS DataBase Reference: cyclohexane-1,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: cyclohexane-1,3-diol(823-18-7)
• EPA Substance Registry System: cyclohexane-1,3-diol(823-18-7)

Safety Data

• Hazardous Substances Data: 823-18-7(Hazardous Substances Data)

Usage

Purification Methods

Crystallise the cis-diol from ethyl acetate and acetone. The dibenzoyl derivative has m 65.5o (from MeOH or pet ether). [Rigby J Chem Soc 1586 1949, Furberg & Hassell Acta Chem Scand 4 518 1950, Beilstein 6 III 4077, 6 IV 5208.]

Upstream product

• 822-67-3 Cyclohex-2-enol 
• 64-17-5 ethanol 
• 108-46-3 recorcinol 
• 7732-18-5 water 
• 5515-64-0 trans-1,3-cyclohexanediol 
• 30182-67-3 1,3-Cyclohexanedione 
• 302577-72-6 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexan-1-one 
• 930-68-7 cyclohexenone 
• 2699-20-9 (1S,2R,3R)-2-Bromo-3-methoxy-cyclohexanol 
• 130256-36-9 (1S,3S,5R)-1-acetoxy-5-benzyloxy-3-cyclohexanol 
• 131245-94-8 (S)-5-benzyloxy-2-cyclohexen-1-one 
• 130256-34-7 meso-1,3-cis,3,5-cis-1,3-diacetoxy-5-benzyloxycyclohexane 
• 504-01-8 cyclohexane-1,3-diol 
• 108-93-0 cyclohexanol 

Downstream Products

• 1227567-89-6 cis-1,3-bis-phosphonooxy-cyclohexane 
• 930-68-7 cyclohexenone 
• 832-09-7 (1R^*,3S^*)-1,3-cyclohexanediol diacetate 
• 140460-25-9 cis-1,3-dibenzyloxycyclohexane 
• 888025-01-2 (1S,3R)-3-(2,2,2-trideuterioacetoxy)-1-cyclohexanol 
• 109511-54-8 cis-1,3-bis-(4-bromo-benzenesulfonyloxy)-cyclohexane 

Relevant articles and documents

Selective Isomerization via Transient Thermodynamic Control: Dynamic Epimerization of trans to cis Diols

Traditional approaches to stereoselective synthesis require high levels of enantio- and diastereocontrol in every step that forms a new stereocenter. Here, we report an alternative approach, in which the stereochemistry of organic substrates is selectivel

Acylative desymmetrization of cyclic meso-1,3-diols by chiral DMAP derivatives

An efficient enantioselective acylative desymmetrization of cyclic meso-1,3-diols was developed by using a chiral DMAP derivative 1e having a 1,1¤-binaphthyl unit. The reactions required only 0.5mol% of the catalyst and showed good to excellent enantioselectivity. With this transformation, 5a, a key building block for the synthesis of natural products, was easily obtained in almost enantiomerically pure form after a single recrystallization. Control experiments revealed that tert-alcohol units on the catalyst were responsible for both the catalytic activity and enantioselectivity.

Efficient and Practical Arene Hydrogenation by Heterogeneous Catalysts under Mild Conditions

An efficient and practical arene hydrogenation procedure based on the use of heterogeneous platinum group catalysts has been developed. Rh/C is the most effective catalyst for the hydrogenation of the aromatic ring, which can be conducted in iPrOH under neutral conditions and at ordinary to medium H 2 pressures (10 atm). A variety of arenes such as alkylbenzenes, benzoic acids, pyridines, furans, are hydrogenated to the corresponding cyclohexyl and heterocyclic compounds in good to excellet yields. The use of Ru/C, less expensive than Rh/C, affords an effective and practical method for the hydrogenation of arenes including phenols. Both catalysts can be reused several times after simple filtration without any significant loss of catalytic activity.