trans-1,2-Cyclohexanediol

Base Information

• Chemical Name: trans-1,2-Cyclohexanediol
• CAS No.: 1460-57-7
• Molecular Formula: C6H12O2
• Molecular Weight: 116.16
• Hs Code.: 2906 19 00
• European Community (EC) Number: 215-956-6
• UNII: 89G7G95Z1Y,8W5CKZ32GP
• DSSTox Substance ID: DTXSID7075347
• Nikkaji Number: J36.939J
• Wikidata: Q27102137
• Metabolomics Workbench ID: 49876
• Mol file: 1460-57-7.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 trans-1,2-Cyclohexanediol

Chemical Property:

• Appearance/Colour: Off-white crystals or crystalline powder
• Vapor Pressure: 0.00839mmHg at 25°C
• Melting Point: 101-104 °C(lit.)
• Refractive Index: 1.526
• 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
• Storage Temp.: -20°C Freezer
• Solubility.: Soluble in chloroform and methanol.
• 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:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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: trans-1,2-Cyclohexanediol is used as an organic chemical synthesis intermediate.

Technology Process of trans-1,2-Cyclohexanediol

There total 248 articles about trans-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: 97.0%

cyclohexene (110-83-8) → trans-1,2-cyclohexandiol (1460-57-7) + cyclohexane-1,2-epoxide (286-20-4)

Guidance literature:

With dihydrogen peroxide; magnesium sulfate; methyltrioxorhenium(VII); In tert-butyl alcohol; at 82 ℃; for 0.1h; Product distribution; Kinetics; Mechanism; further alkenes, further conditions;

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: 75.2%

cyclohexene (110-83-8) → (+)-trans-2-isopropoxycyclohexan-1-ol (2979-30-8,60421-37-6,134070-80-7,134108-70-6) + trans-1,2-cyclohexandiol (1460-57-7) + cyclohexane-1,2-epoxide (286-20-4)

Guidance literature:

ortho-tungstic acid; In isopropyl alcohol; at 50 ℃; for 15h;

DOI:10.1246/bcsj.58.3193

upstream raw materials:

1-acetoxy-2-iodocyclohexane

1-chloro-2-iodocyclohexane

(S)-α-hydroxycyclohexanone

((1R)-menthyloxy)-acetic acid-((1R)-2t-hydroxy-cyclohexyl-(1r)-ester)

Downstream raw materials:

(+/-)-2-phenoxy-(3ar,7at)-hexahydro-benzo[1,3,2]dioxaphosphole

cyclopentanealdehyde

Adipic acid

(+/-)-trans-decahydro-benzo[b][1,4]dioxecin-2,7-dione

Refernces

• 1、 Otake, Ken-Ichi,Ahn, Sol,Knapp, Julia,Hupp, Joseph T.,Notestein, Justin M.,Farha, Omar K.. "Vapor-Phase Cyclohexene Epoxidation by Single-Ion Fe(III) Sites in Metal-Organic Frameworks". . p. 2457 - 2463. Retrieved 2021.
• 2、 Yang, Qiusheng,Yang, Xue,Wang, Yanji,Wang, Haiou,Cheng, Qingyan. "A green route to 1,2-cyclohexanediol via the hydrolysis of cyclohexene oxide catalyzed by water". . p. 2277 - 2284. Retrieved 2012.
• 3、 Fraile, Jose M.,Garcia, Jose I.,Mayoral, Jose A.,Vispe, Eugenio. "Silica-Supported Titanium Derivatives as Catalysts for the Epoxidation of Alkenes with Hydrogen Peroxide: A New Way to Tuneable Catalytic Activity through Ligand Exchange". . p. 40 - 40. Retrieved 2000.
• 4、 Fraile,Garcia,Mayoral,Vispe,Brown,Naderi. "Is MCM-41 really advantageous over amorphous silica? The case of grafted titanium epoxidation catalysts". . p. 1510 - 1511. Retrieved 2001.
• 5、 Zhang, Zhaorong,Suo, Jishuan,Zhang, Xiaoming,Li, Shuben. "Synthesis of highly active tungsten-containing MCM-41 mesoporous molecular sieve catalyst". . p. 241 - 242. Retrieved 1998.
• 6、 Ahn, Sol,Thornburg, Nicholas E.,Li, Zhanyong,Wang, Timothy C.,Gallington, Leighanne C.,Chapman, Karena W.,Notestein, Justin M.,Hupp, Joseph T.,Farha, Omar K.. "Stable metal-organic framework-supported niobium catalysts". . p. 11954 - 11961. Retrieved 2016.
• 7、 Benfatti, Fides,Cardillo, Giuliana,Gentilucci, Luca,Tolomelli, Alessandra,Monari, Magda,Piccinelli, Fabio. "A microwave-enhanced, lewis acid-catalyzed synthesis of 1,3-dioxolanes and oxazolines from epoxides". . p. 1256 - 1264. Retrieved 2007.
• 8、 Yamashita, Tomohiro,Lu, Daling,Kondo, Junko N.,Hara, Michikazu,Domen, Kazunari. "Preparation and Catalytic Application of Transition Metal (Fe, V, or Cu) Oxides Homogeneously Dispersed in the Wall of Mesoporous Nb2O 5". . p. 1034 - 1035. Retrieved 2003.
• 9、 -. "A method for preparation of cycloalkane diols". Paragraph 0058-0083. . Retrieved 2021/06/09.
• 10、 Ahn, Sol,Ardagh, M. Alexander,Farha, Omar K.,Hicks, Kenton E.,Nauert, Scott L.,Notestein, Justin M.,Schweitzer, Neil M.. "Demonstrating the Critical Role of Solvation in Supported Ti and Nb Epoxidation Catalysts via Vapor-Phase Kinetics". . p. 2817 - 2825. Retrieved 2020/03/11.