(1R,2R)-1,2-Cyclohexanedimethanol

Base Information

• Chemical Name: (1R,2R)-1,2-Cyclohexanedimethanol
• CAS No.: 65376-05-8
• Molecular Formula: C8H16O2
• Molecular Weight: 144.214
• Hs Code.: 2906199090
• European Community (EC) Number: 607-783-3,692-053-7
• DSSTox Substance ID: DTXSID101285244
• Nikkaji Number: J36.673K
• Wikidata: Q76416808
• Mol file: 65376-05-8.mol

Synonyms:(1R,2R)-1,2-Cyclohexanedimethanol;65376-05-8;(1R,2R)-Cyclohexane-1,2-diyldimethanol;trans-Cyclohexane-1,2-diyldimethanol;25712-33-8;[(1R,2R)-2-(hydroxymethyl)cyclohexyl]methanol;trans-1,2-Cyclohexanedimethanol;trans-1,2-Bis(hydroxymethyl)cyclohexane;1,2-Cyclohexanedimethanol, (1R-trans)-;1,2-Cyclohexanedimethanol, (1R,2R)-rel-;MFCD16660860;(1R,2R)-1,2-Bis(hydroxymethyl)cyclohexane;SCHEMBL130805;AMY5218;XDODWINGEHBYRT-YUMQZZPRSA-N;DTXSID101285244;AKOS016000198;CS-O-32225;rel-(1R,2R)-1,2-Cyclohexanedimethanol;AC-22678;DS-17552;(1R)-Cyclohexane-1beta,2alpha-dimethanol;C2978;CS-0028229;A848236;A1-00282;J-500290

Chemical Property of (1R,2R)-1,2-Cyclohexanedimethanol

Chemical Property:

• Melting Point: 63.0 to 67.0 °C
• Boiling Point: 270.1 °C at 760 mmHg
• PKA: 14.75±0.10(Predicted)
• Flash Point: 129 °C
• PSA: 40.46000
• Density: 1.004 g/cm³
• LogP: 0.77740
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 144.115029749
• Heavy Atom Count: 10
• Complexity: 81.3

Purity/Quality:

99%min ^*data from raw suppliers

(1R,2R)-1,2-Cyclohexanedimethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C(C1)CO)CO
• Isomeric SMILES: C1CC[C@H]([C@@H](C1)CO)CO
• Uses: (1R,2R)-1,2-Cyclohexanedimethanol (cas# 65376-05-8) is a compound useful in organic synthesis.

Technology Process of (1R,2R)-1,2-Cyclohexanedimethanol

There total 22 articles about (1R,2R)-1,2-Cyclohexanedimethanol 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: 80.0%

(-)-(1R,2R)-trans-2-(hydroxymethyl)cyclohexanoic acid (65376-04-7) → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8,25712-33-8)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 12h; Heating;

DOI:10.1021/ja00381a024

Reference yield: 76.0%

bis(D-menthyl) (1R,2R)-cyclohexane-1,2-dicarboxylate → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8,25712-33-8)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 - 20 ℃; for 19h; Inert atmosphere;

DOI:10.1039/c6ob01358a

Reference yield:

(3aR,7aS)-1,3,3a,4,7,7a-hexahydroisobenzofuran-1-one (65376-03-6) → (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane (65376-05-8,25712-33-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / H₂ / Pd/C / methanol

2: 34 percent / NaOH / H₂O / 192 h / 130 °C

3: 80 percent / LiAlH₄ / diethyl ether / 12 h / Heating

With sodium hydroxide; lithium aluminium tetrahydride; hydrogen; palladium on activated charcoal; In methanol; diethyl ether; water;

DOI:10.1021/ja00381a024

upstream raw materials:

(+/-)-trans-2-(hydroxymethyl)cyclohexylmethanol

(-)-(1R,2R)-trans-2-(hydroxymethyl)cyclohexanoic acid

(1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester

diethyl trans-1,2,3,6-tetrahydrophthalate

Downstream raw materials:

(1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate

Refernces

• 1、 -. "Method for efficiently synthesizing 1R,2R-cyclohexanedimethanol by gas-solid phase technology". Paragraph 0062-0073. . Retrieved 2020/01/25.
• 2、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF LURASIDONE HYDROCHLORIDE". . . Retrieved 2016/05/24.