2-Hydroxymethylcyclohexanol

Base Information

• Chemical Name: 2-Hydroxymethylcyclohexanol
• CAS No.: 27583-43-3
• Molecular Formula: C7H14 O2
• Molecular Weight: 130.187
• Hs Code.: 2906199090
• DSSTox Substance ID: DTXSID20409172
• Nikkaji Number: J1.394.249H
• Mol file: 27583-43-3.mol

Synonyms:2-HYDROXYMETHYLCYCLOHEXANOL;27583-43-3;2-(hydroxymethyl)cyclohexan-1-ol;2-(Hydroxymethyl)cyclohexanol;2-Hydroxycyclohexanemethanol;SCHEMBL282874;DTXSID20409172;2-(hydroxymethyl)-cyclohexan-1-ol;CBA58343;AKOS006295144;FT-0719899;EN300-217936;Z1198163949

Chemical Property of 2-Hydroxymethylcyclohexanol

Chemical Property:

• Vapor Pressure: 0.00193mmHg at 25°C
• Refractive Index: 1.493
• Boiling Point: 259.2°C at 760 mmHg
• Flash Point: 125.4°C
• PSA: 40.46000
• Density: 1.066g/cm³
• LogP: 0.52980
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 130.099379685
• Heavy Atom Count: 9
• Complexity: 83

Purity/Quality:

98%min ^*data from raw suppliers

2-Hydroxymethylcyclohexanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C(C1)CO)O

Technology Process of 2-Hydroxymethylcyclohexanol

There total 80 articles about 2-Hydroxymethylcyclohexanol 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: 91.0%

(1R,2S)-ethyl 2-hydroxycyclohexanecarboxylate (1655-06-7,6125-55-9,6149-52-6,29569-79-7,61586-78-5,77026-73-4,119068-36-9,119068-37-0,3444-72-2) → 2-(hydroxymethyl)cyclohexanol (27583-43-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 25 ℃; for 2h; Inert atmosphere;

Reference yield: 90.0%

2-(hydroxymethyl)cyclohexanone (5331-08-8) → cis-2-(hydroxymethyl)cyclohexanol (4187-60-4,27583-43-3,29569-80-0,51606-49-6,51606-50-9,69308-85-6,96553-66-1,106758-67-2,4187-59-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 12h; Ambient temperature;

DOI:10.1021/jo00208a014

Reference yield: 74.0%

2-(hydroxymethyl)cyclohexanone (5331-08-8) → 2-(hydroxymethyl)cyclohexanol (27583-43-3)

Guidance literature:

With magnesium; mercury dichloride; In ethanol; at 20 ℃; for 12h;

DOI:10.1016/j.tetlet.2005.10.140

upstream raw materials:

ethyl (1S,2S)-2-hydroxycyclohexanecarboxylate

(1S)-trans-2-hydroxy-cyclohexanecarboxylic acid

trans-2-hydroxycyclohexanecarboxylic acid

ethyl 2-oxocyclohexane carboxylate

Downstream raw materials:

1-bromo-2-(bromomethyl)cyclohexane

4-Propoxy-benzoic acid (2R,4aR,8aS)-4-(hexahydro-benzo[1,3]dioxin-2-yl)-phenyl ester

4-Methyl-benzoic acid (2R,4aR,8aS)-4-(hexahydro-benzo[1,3]dioxin-2-yl)-phenyl ester

(2R,4aR,8aS)-4-(Hexahydro-benzo[1,3]dioxin-2-yl)-benzoic acid 4-pentyl-phenyl ester

Refernces

• 1、 Macmillan, David W. C.,Oswood, Christian J.. "Selective Isomerization via Transient Thermodynamic Control: Dynamic Epimerization of trans to cis Diols". . p. 93 - 98. Retrieved 2022/01/03.
• 2、 Zhang, Tian,Redden, Brandon K.,Wiskur, Sheryl L.. "Investigation of Electrostatic Interactions towards Controlling Silylation-Based Kinetic Resolutions". supporting information. p. 4827 - 4831. Retrieved 2019/08/12.