cis-1,2-Cyclohexanediol

Base Information

• Chemical Name: cis-1,2-Cyclohexanediol
• CAS No.: 1792-81-0
• Molecular Formula: C6H12O2
• Molecular Weight: 116.16
• Hs Code.: 29061990
• UNII: G9FB3QY86K
• DSSTox Substance ID: DTXSID701016514
• Nikkaji Number: J46.541K
• Wikidata: Q27114877
• Metabolomics Workbench ID: 54537
• Mol file: 1792-81-0.mol

Synonyms:1,2-cyclohexanediol;1,2-cyclohexanediol, (cis)-isomer;1,2-cyclohexanediol, (trans)-isomer;cis-1,2-cyclohexanediol;trans-1,2-cyclohexanediol

Chemical Property of cis-1,2-Cyclohexanediol

Chemical Property:

• Appearance/Colour: White crystals crystalline powder.
• Melting Point: 97-101 °C(lit.)
• Refractive Index: 1.4270 (estimate)
• Boiling Point: 236.716 °C at 760 mmHg
• PKA: 14.49±0.40(Predicted)
• Flash Point: 114.252 °C
• PSA: 40.46000
• Density: 1.157 g/cm³
• LogP: 0.28220
• Solubility.: soluble in Methanol
• Water Solubility.: slightly soluble
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 116.083729621
• Heavy Atom Count: 8
• Complexity: 62.9

Purity/Quality:

98% ^*data from raw suppliers

cis-1,2-Cyclohexanediol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: C1CCC(C(C1)O)O
• Isomeric SMILES: C1CC[C@@H]([C@@H](C1)O)O
• Uses: cis-1,2-Cyclohexanediol is a reagent used in the synthesis of boronic esters of corannulene which are used to prepare icosahedral supramolecules.

Technology Process of cis-1,2-Cyclohexanediol

There total 337 articles about cis-1,2-Cyclohexanediol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.3%

cyclohexene (110-83-8) → cyclohexenone (930-68-7) + (1R,2R)-trans-1,2-cyclohexanediol (1072-86-2,1460-57-7,1792-81-0,54383-22-1,57794-08-8,931-17-9) + Cyclohex-2-enol (822-67-3)

Guidance literature:

With tungsten(VI) oxide dihydrate; phosphoric acid; dihydrogen peroxide; In water; at 70 ℃; for 3h;

DOI:10.1016/j.apcata.2013.06.023

Reference yield: 60.0%

cyclohexene (110-83-8) → cyclohexenone (930-68-7) + cis-1,2-cyclohexane (1792-81-0) + hexanedial (1072-21-5) + Cyclohex-2-enol (822-67-3)

Guidance literature:

With cis-[Ru(1,4,7-trimethyl-1,4,7-triazacyclononane)O₂(trifluoroacetate)]ClO₄; In water; tert-butyl alcohol; at 20 ℃; for 14h;

DOI:10.1021/ja0528230

Reference yield:

C13H18O3 → (1R,2R)-trans-1,2-cyclohexanediol (1072-86-2,1460-57-7,1792-81-0,54383-22-1,57794-08-8,931-17-9) + benzaldehyde (100-52-7)

Guidance literature:

In benzene-d6; Equilibrium constant;

DOI:10.1021/ja0756366

upstream raw materials:

dioxin

1-methyl-4-nitrosobenzene

(+/-)-cis-2-(toluene-sulfonyl-⁽⁴⁾-oxy)-1-acetoxy-cyclohexane

cis-1,2-diacetoxycyclohexane

Downstream raw materials:

cis-1,2-diacetoxycyclohexane

cis-1-acetoxycyclohexane-2-ol

cis-1,2-Dibenzoyloxycyclohexane

cis-benzoic acid 2-hydroxycyclohexyl ester

Refernces

• 1、 Feistel, Felix,Paetz, Christian,Lorenz, Sybille,Beran, Franziska,Kunert, Grit,Schneider, Bernd. "Idesia polycarpa (Salicaceae) leaf constituents and their toxic effect on Cerura vinula and Lymantria dispar (Lepidoptera) larvae". . p. 170 - 179. Retrieved 2017.
• 2、 Edward et al.. "". . . Retrieved 1977.
• 3、 Scott,Fenton. "-". . p. 681. Retrieved 1970.
• 4、 Erdik, Ender,Matteson, Donald S.. "Kinetics of Osmium Tetraoxide Catalyzed Trimethylamine N-Oxide Oxidations of Cyclohexene and α-Pinene to Diols". . p. 2742 - 2748. Retrieved 1989.
• 5、 Lyakin, Oleg Y.,Bryliakov, Konstantin P.,Talsi, Evgenii P.. "EPR, 1H and 2H NMR, and reactivity studies of the iron-oxygen intermediates in bioinspired catalyst systems". . p. 5526 - 5538. Retrieved 2011.
• 6、 Shteinman. "Structure and catalytic activity of a new iron(ii) complex with a tetradentate carboxamide ligand: The effect of the outer-sphere donor on the chemoselectivity of the metal complex catalyst". . p. 1328 - 1334. Retrieved 2012.
• 7、 Brutcher,Evans. "-". . p. 618. Retrieved 1958.
• 8、 Macmillan, David W. C.,Oswood, Christian J.. "Selective Isomerization via Transient Thermodynamic Control: Dynamic Epimerization of trans to cis Diols". supporting information. p. 93 - 98. Retrieved 2022/01/03.
• 9、 Li, Yutang,Lidskog, Anna,Armengol-Relats, Helena,Pham, Thanh Huong,Favraud, Antoine,Nicolas, Maxime,Dawaigher, Sami,Xiao, Zeyun,Ma, Dayou,Lindb?ck, Emil,Strand, Daniel,W?rnmark, Kenneth. "Enantiotopic Discrimination by Coordination-Desymmetrized meso-Ligands". . p. 1575 - 1579. Retrieved 2020/02/04.