[1S,2S,(-)]-1,2-Cyclohexanedimethanol

Base Information

• Chemical Name: [1S,2S,(-)]-1,2-Cyclohexanedimethanol
• CAS No.: 3205-34-3
• Molecular Formula: C8H16O2
• Molecular Weight: 144.214
• Hs Code.: 2906199090
• Mol file: 3205-34-3.mol

Synonyms:1,2-Cyclohexanedimethanol, (+)-trans- (8CI);1,2-Cyclohexanedimethanol, (1S-trans)-;trans-(+)-1,2-Bis(hydroxymethyl)cyclohexane;(S,S)-1,2-Bis(hydroxymethyl)cyclohexane;(1S,2S)-1,2-Bis(hydroxymethyl)cyclohexane;

Chemical Property of [1S,2S,(-)]-1,2-Cyclohexanedimethanol

Chemical Property:

• Melting Point: 60-63℃
• Boiling Point: 270.082 °C at 760 mmHg
• Flash Point: 128.974 °C
• PSA: 40.46000
• Density: 1.004 g/cm³
• LogP: 0.77740
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1S,?2S)?-1,?2-?Cyclohexanedimethano?l ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (1S,?2S)?-1,?2-?Cyclohexanedimethano?l is an intermediate used to synthesize C2-?symmetrical diphosphines using chiral zinc organometallics.

Technology Process of [1S,2S,(-)]-1,2-Cyclohexanedimethanol

There total 6 articles about [1S,2S,(-)]-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: 99.0%

(4S,5S)-4,5-bis(hydroxymethyl)cyclohexene (15679-27-3) → (1S,2S)-(–)-1,2-di(hydroxymethyl)cyclohexane (3205-34-3,25712-33-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 1.5h; under 1654.9 Torr;

DOI:10.1021/jo951647i

Reference yield: 98.0%

(1S,2S)-cyclohexane-1,2-dicarboxylic acid (610-10-6,1687-30-5,2305-32-0,21963-41-7,46022-05-3,610-09-3) → (1S,2S)-(–)-1,2-di(hydroxymethyl)cyclohexane (3205-34-3,25712-33-8)

Guidance literature:

(1S,2S)-cyclohexane-1,2-dicarboxylic acid; With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 60 ℃; Inert atmosphere;

With water; sodium hydroxide; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201002990

Reference yield: 80.0%

(1S,2S)-(+)-cyclohexane-1,2-dicarboxylic acid dimethyl ester (31982-90-8) → (1S,2S)-(–)-1,2-di(hydroxymethyl)cyclohexane (3205-34-3,25712-33-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 3.25h; Cooling with ice;

DOI:10.1039/c8nj05750h

upstream raw materials:

(1S,2S)-cyclohexane-1,2-dicarboxylic acid

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

(4S,5S)-4,5-bis(hydroxymethyl)cyclohexene

trans-1,2-cyclohexanedicarboxylic acid

Downstream raw materials:

(1S,2S)-1,2-bis(bromomethyl)cyclohexane

Refernces

• 1、 Alfuth, Jan,Chojnacki, Jaros?aw,Po?oński, Tadeusz,Olszewska, Teresa. "Induction of chirality in 4,4′-azopyridine by halogen-bonding interaction with optically active ditopic donors". . p. 5512 - 5517. Retrieved 2019/04/04.
• 2、 Zhang, Xiaowei,Huang, Kexuan,Hou, Guohua,Cao, Bonan,Zhang, Xumu. "Electron-donating and rigid p-stereogenic bisphospholane ligands for highly enantioselective rhodium-catalyzed asymmetric hydrogenations". supporting information; experimental part. p. 6421 - 6424. Retrieved 2010/12/19.