(1S,2S)-cyclohexane-1,2-diol

Base Information

• Chemical Name: (1S,2S)-cyclohexane-1,2-diol
• CAS No.: 57794-08-8
• Molecular Formula: C6H12O2
• Molecular Weight: 116.16
• Hs Code.: 29061990
• European Community (EC) Number: 625-666-5
• UNII: 3RX9RD438J
• Nikkaji Number: J36.940C
• Wikidata: Q27454285
• Mol file: 57794-08-8.mol

Synonyms:(1S,2S)-cyclohexane-1,2-diol;57794-08-8;(1S,2S)-trans-1,2-Cyclohexanediol;1,2-Cyclohexanediol, (1S,2S)-;(1S)-trans-1,2-Cyclohexanediol;1,2-Cyclohexanediol, (1S-trans)-;1alpha,2beta-Cyclohexanediol;(S,S)-1,2-Cyclohexanediol;(1s,2s)-trans-cyclohexanediol;3RX9RD438J;(1s,2s)-1,2-cyclohexanediol;(+)-trans-1,2-Cyclohexanediol;(+)-1S,2S-1,2-Cyclohexanediol;J36.940C;1,2-trans-Cyclohexanediol;trans-1,2-Dihydroxycyclohexane;MFCD00063611;UNII-3RX9RD438J;SCHEMBL379844;1,2-Cyclohexanediol, (E)-;BDBM36072;BCP16536;AKOS016038175;"TRANS-CYCLOHEXANE-1,2-DIOL";1.ALPHA.,2.BETA.-CYCLOHEXANEDIOL;AS-77640;(1S,2S)-trans-1,2-Cyclohexanediol, 99%;CS-0180922;EN300-177050;F86109;Q27454285

Chemical Property of (1S,2S)-cyclohexane-1,2-diol

Chemical Property:

• Melting Point: 107-109 °C(lit.)
• Refractive Index: 1.526
• Boiling Point: 236.7°Cat760mmHg
• PKA: 14.49±0.40(Predicted)
• Flash Point: 114.3°C
• PSA: 40.46000
• Density: 1.156g/cm³
• LogP: 0.28220
• 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%,99%, ^*data from raw suppliers

(1S,2S)-trans-1,2-Cyclohexanediol 99% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCC(C(C1)O)O
• Isomeric SMILES: C1CC[C@@H]([C@H](C1)O)O
• Uses: (1S,2S)-trans-1,2-Cyclohexanediol may be used in the preparation of (1S,2S)-1,2-cyclohexanediyl bis(4-vinylbenzoate) by reacting with 4-vinylbenzoyl chloride. It may also be used as a chiral ligand for the preparation of non-racemic hydroxy phosphonates via titanium alkoxide-catalyzed addition of dimethyl phosphite to the corresponding aldehydes.

Technology Process of (1S,2S)-cyclohexane-1,2-diol

There total 265 articles about (1S,2S)-cyclohexane-1,2-diol 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: 45.0%

trans-1,2-cyclohexandiol (1460-57-7) + benzaldehyde (100-52-7) → (1R,2R)-trans-1,2-cyclohexanediol (1072-86-2,1460-57-7,1792-81-0,54383-22-1,57794-08-8,931-17-9) + 2-hydroxy-2-phenylacetophenone (119-53-9,579-44-2) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With 5a(S),10b(R)-5a,10b-dihydro-2-(pentafluorophenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium tetrafluoroborate; 3-benzyl-2',3',4',5'-tetraacetylriboflavin; triethylamine; In chloroform; at 20 ℃; for 3h; optical yield given as %ee; enantioselective reaction; Resolution of racemate; Air; Molecular sieve;

DOI:10.1002/chem.201100737

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:

cis-1,2-cyclohexane

(1S,2S)-trans-1,2-cyclohexanediol diacetate

(+)-(R,R)-benzylcyclohexan-1,2-diol

trans-1,2-cyclohexandiol

Downstream raw materials:

trans-1,2-dipicryloxycyclohexane

trans-2-picryloxy-1-cyclohexanole

((1S,5S,6S)-3-Methyl-bicyclo[3.2.1]oct-3-en-6-yl)-acetic acid (1S,2S)-2-hydroxy-cyclohexyl ester

((1R,5R,6R)-3-Methyl-bicyclo[3.2.1]oct-3-en-6-yl)-acetic acid (1S,2S)-2-hydroxy-cyclohexyl ester

Refernces

• 1、 -. "SYNTHESIS AND APPLICATION OF CHIRAL SUBSTITUTED POLYVINYLPYRROLIDINONES". Paragraph 0046; 0047; 0049. . Retrieved 2020/11/24.
• 2、 Jin, Manman,Niu, Qingtao,Guo, Zhenmei,Lv, Zhiguo. "Epoxidation of cyclohexene with H2O2 over efficient water-tolerant heterogeneous catalysts composed of mono-substituted phosphotungstic acid on co-functionalized SBA-15". . . Retrieved 2019/07/31.