931-71-5

Basic information

• Product Name: CIS-1,4-CYCLOHEXANEDIOL
• Synonyms: CIS-1,4-CYCLOHEXANEDIOL;cis-cyclohexane-1,4-diol;TRANS-1,4-CYLCLOHEXANEDIOL;cis-4-cyclohexanediol;cis-Chinit;cis-Hexahydrohydroquinone;cis-Quinitol;cis-1,4-Dihydroxycyclohexane
• CAS NO: 931-71-5
• Molecular Formula: C₆H₁₂O₂
• Molecular Weight: 116.16
• EINECS: 213-240-8
• Product Categories: Pharmaceutical Intermediates
• Mol File: 931-71-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: 98-100 ºC
• Boiling Point: 150 ºC
• Flash Point: 65 ºC
• Appearance: /
• Density: 1.156g/cm³
• Refractive Index: 1.526
• Storage Temp.: 2-8°C
• PKA: 14.75±0.40(Predicted)
• CAS DataBase Reference: CIS-1,4-CYCLOHEXANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-1,4-CYCLOHEXANEDIOL(931-71-5)
• EPA Substance Registry System: CIS-1,4-CYCLOHEXANEDIOL(931-71-5)

Safety Data

• Hazardous Substances Data: 931-71-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 931-71-5 differently. You can refer to the following data:
1. cis-1,4-Cyclohexanediol is an metabolite of side-chain of candesartan cilexetil (C175580), on digoxin-induced arrhythmias in dogs with congestive heart failure.
2. cis-1,4-Cyclohexanediol is a metabolite of the side-chain of candesartan cilexetil (C175580), on digoxin-induced arrhythmias in dogs with congestive heart failure.

Purification Methods

Crystallise the cis-diol from acetone (charcoal), then dry and sublime it under vacuum. It also crystallises from Me2CO or Me2CO/*C6H6. The diacetate has m 40.6-41.1o (from pet ether or 34-36o from EtOH). [Grob & Baumann Helv Chim Acta 38 604 1955, Owen & Robins J Chem Soc 320 1949, Beilstein 6 III 4080, 6 IV 5209.]

InChI:InChI=1/C6H12O2/c7-5-1-2-6(8)4-3-5/h5-8H,1-4H2/t5-,6+

Upstream product

• 1165952-91-9 cyclohexa-1,3-diene 
• 123-31-9 hydroquinone 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 124-38-9 carbon dioxide 
• 637-88-7 1,4-Cyclohexanedione 
• 108-93-0 cyclohexanol 
• 94110-79-9 4-<(p-chlorobenzoyl)oxy>cyclohexanone 

Downstream Products

• 37393-54-7 trans-1,4-cyclohexanediol dimethanesulfonate 
• 86602-62-2 cis-1,4-diiodo-cyclohexane 
• 50570-92-8 cis-Cyclohexan-1,4-diol-tetrahydrogen-diphosphat 
• 127074-28-6 cis-4-(benzyloxy)cyclohexanol 
• 822-66-2 3-cyclohexen-1-ol 
• 6995-79-5 cyclohexane-1,4-diol 
• 6289-83-4 trans-1,4-diacetoxy-cyclohexane 
• 279-49-2 7-oxabicyclo(2.2.1)heptane 
• 42742-00-7 cis-1,4-diacetoxy-cyclohexane 
• 16890-91-8 trans-1,4-dichlorocyclohexane 
• 16749-11-4 1,4-cis-dichlorocyclohexane 
• 2975-92-0 d,l-(1,2,3/4)-cyclohexanetetrol 
• 35541-65-2 trans-1.4-bis-phenylcarbamoyloxy-cyclohexane 
• 862728-45-8 cis-4-(2-hydroxy-2-methyl-propoxy)-cyclohexanol 

Relevant articles and documents

Synthetic method for cis-1,4-cyclohexanediol

The invention discloses a synthetic method for cis-1,4-cyclohexanediol, belonging to the field of organic chemical synthesis. According to the method, 4-(alkylacyloxy)cyclohexanone is used as a raw material and is only subjected to reduction and hydrolysis so as to conveniently synthesize cis-1,4-cyclohexanediol. The method can guarantee high selectivity of the reactions, and is high in the yieldof cis-1,4-cyclohexanediol and suitable for large-scale production.

Triphenylphosphine reduction of saturated endoperoxides

(Figure Presented) Triphenylphosphine reduction of saturated endoperoxides derived from 6,6-dimethylfulvene and spiro[2.4]hepta-4,6-diene in the presence of nucleophiles results in the formation of products that mainly stem from deoxygenation followed by carbocation formation. Nucleophilic attack by solvent proceeds by an SN1 like mechanism; allyl shifts and cyclopropylcarbinyl-cyclobutyl rearrangements also occur. With the systems lacking carbocation-stabilizing groups, the deoxygenation step is preceded by attack of H2O at the phosphorus.

Pathways of liquid-phase oxidation of cyclohexanol

The kinetics of product accumulation in uncatalyzed oxidation of cyclohexanol at 403 K was studied. Along with the compounds originating from oxidation of cyclohexanol at position 1 (cyclohexanone, hydrogen peroxide, 1-hydroxycyclohexyl hydroperoxide), products formed by oxidation of C-H bonds at positions 2-4 were detected: 2-, 3-, and 4-hydroxycyclohexyl hydroperoxides (cis and trans isomers), 1,2-, 1,3-, and 1,4-dihydroxycyclohexanes (cis and trans isomers), 2- and 4-hydroxycyclohexanones, and 2-cyclohexenone.