CIS-1,4-CYCLOHEXANEDIOL Chemical Properties

Melting point:

98-100 ºC

Boiling point:

150 ºC

Density 

1.156±0.06 g/cm3(Predicted)

Flash point:

65 ºC

storage temp. 

2-8°C

pka

14.75±0.40(Predicted)

InChI

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

InChIKey

VKONPUDBRVKQLM-OLQVQODUSA-N

SMILES

[C@@H]1(O)CC[C@H](O)CC1

CAS DataBase Reference

931-71-5

EPA Substance Registry System

1,4-Cyclohexanediol, cis- (931-71-5)

Safety Information

HS Code 

2906.19.5000

CIS-1,4-CYCLOHEXANEDIOL Usage And Synthesis

Uses

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.]

Structure and conformation

Chair conformation:
this form of cis-1, 4-cyclohexane diol is most stable,

there will be a strong intramolecular hydrogen bonding. In cyclohexane boat form 1, 4 interaction is know as Flagpole interaction which makes it unstable. But in this case, ?OH groups are present instead of hydrogen and there will be a strong hydrogen bonding and no flagpole interaction. Hence, diaxial boat form is more stable.

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