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 
• 279-49-2 7-oxabicyclo(2.2.1)heptane 
• 123-31-9 hydroquinone 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 124-38-9 carbon dioxide 
• 637-88-7 1,4-Cyclohexanedione 
• 7647-01-0 hydrogenchloride 
• 67-66-3 chloroform 
• 67-64-1 acetone 
• 71-43-2 benzene 
• 108-93-0 cyclohexanol 
• 280-53-5 2,3-dioxabicyclo[2.2.2]octane 
• 6289-83-4 1,4-diacetoxycyclohexane 

Downstream Products

• 822-66-2 3-cyclohexen-1-ol 
• 827-52-1 1-phenyl-1-cyclohexane 
• 6995-79-5 cyclohexane-1,4-diol 
• 1165952-92-0 cyclohexa-1,4-diene 
• 1165952-91-9 cyclohexa-1,3-diene 
• 42742-00-7 cis-1,4-diacetoxy-cyclohexane 
• 888709-81-7 cis-1,4-dibenzoyloxy-cyclohexane 
• 6308-92-5 cis-1-Benzoyloxy-cyclohexanol-⁽⁴⁾ 
• 35541-65-2 cis-1.4-bis-phenylcarbamoyloxy-cyclohexane 
• 37393-54-7 trans-1,4-cyclohexanediol dimethanesulfonate 
• 72156-95-7 cis-1-Acetoxy-cyclohexanol-⁽⁴⁾ 
• 132961-64-9 cis-1-p-tolylsulfonyl-4-hydroxy-cyclohexane 
• 120613-04-9 trans-1,4-bis-ethanesulfonyloxy-cyclohexane 
• 100249-54-5 1,4-dimethoxycyclohexane 

Relevant articles and documents

Polysilane-Immobilized Rh-Pt Bimetallic Nanoparticles as Powerful Arene Hydrogenation Catalysts: Synthesis, Reactions under Batch and Flow Conditions and Reaction Mechanism

Hydrogenation of arenes is an important reaction not only for hydrogen storage and transport but also for the synthesis of functional molecules such as pharmaceuticals and biologically active compounds. Here, we describe the development of heterogeneous Rh-Pt bimetallic nanoparticle catalysts for the hydrogenation of arenes with inexpensive polysilane as support. The catalysts could be used in both batch and continuous-flow systems with high performance under mild conditions and showed wide substrate generality. In the continuous-flow system, the product could be obtained by simply passing the substrate and 1 atm H2 through a column packed with the catalyst. Remarkably, much higher catalytic performance was observed in the flow system than in the batch system, and extremely strong durability under continuous-flow conditions was demonstrated (>50 days continuous run; turnover number >3.4 × 105). Furthermore, details of the reaction mechanisms and the origin of different kinetics in batch and flow were studied, and the obtained knowledge was applied to develop completely selective arene hydrogenation of compounds containing two aromatic rings toward the synthesis of an active pharmaceutical ingredient.

Raney ni-al alloy mediated hydrodehalogenation and aromatic ring hydrogenation of halogenated phenols in aqueous medium

Raney Ni-Al alloy in a dilute aqueous alkaline solution has been shown to be a very powerful reducing agent and is highly effective for the reductive dehalogenation of polyhalogenated phenols and aromatic ring hydrogenation of phenols to the corresponding cyclohexanols.

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.