4-(Hydroxymethyl)cyclohexanone

Base Information

• Chemical Name: 4-(Hydroxymethyl)cyclohexanone
• CAS No.: 38580-68-6
• Molecular Formula: C7H12O2
• Molecular Weight: 128.171
• Hs Code.: 2914400090
• European Community (EC) Number: 689-839-7
• DSSTox Substance ID: DTXSID40512455
• Wikidata: Q72485181
• Mol file: 38580-68-6.mol

Synonyms:4-(HYDROXYMETHYL)CYCLOHEXANONE;38580-68-6;4-(Hydroxymethyl)cyclohexan-1-one;MFCD08056334;Cyclohexanone, 4-(hydroxymethyl)-;4-hydroxymethyl cyclohexanone;4-hydroxymethyl-cyclohexanone;SCHEMBL51476;AMY9066;DTXSID40512455;KHMBXNKCMNGLKG-UHFFFAOYSA-N;BCP32846;4-(hydroxymethyl)-cyclohexan-1-one;AKOS015906221;CS-W005330;PS-5745;SY023951;4-(hydroxymethyl)cyclohexanone, AldrichCPR;FT-0744030;EN300-73702;A23352;J-513748

Chemical Property of 4-(Hydroxymethyl)cyclohexanone

Chemical Property:

• Vapor Pressure: 0.00688mmHg at 25°C
• Refractive Index: 1.472
• Boiling Point: 239.8 °C at 760 mmHg
• PKA: 14.85±0.10(Predicted)
• Flash Point: 98 °C
• PSA: 37.30000
• Density: 1.054 g/cm³
• LogP: 0.73800
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 128.083729621
• Heavy Atom Count: 9
• Complexity: 99.5

Purity/Quality:

99% ^*data from raw suppliers

4-(Hydroxymethyl)cyclohexanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)CCC1CO
• Uses: 4-(Hydroxymethyl)cyclohexanone is a reagent used for the preparation of indazoles and benzisoxazoles containing cyclohexylazetidine moieties which are CCR2 antagonists with good hERG selectivity.

Technology Process of 4-(Hydroxymethyl)cyclohexanone

There total 10 articles about 4-(Hydroxymethyl)cyclohexanone 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: 100.0%

4-(hydroxymethyl)cyclohexan-1-ol (33893-85-5) → 4-hydroxymethyl-cyclohexanone (38580-68-6)

Guidance literature:

With sodium hypochlorite; acetic acid; at 20 ℃; for 1h;

DOI:10.1002/ejoc.201301397 DOI:10.1002/ejoc.201301397

Reference yield: 88.0%

ethyl 4-oxocyclohexane-1-carboxylate (17159-79-4) → 4-hydroxymethyl-cyclohexanone (38580-68-6)

Guidance literature:

ethyl 4-oxocyclohexane-1-carboxylate; With n-butyllithium; trimethylaluminum; N,O-dimethylhydroxylamine*hydrochloride; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 2h;

With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 0.5h;

DOI:10.1021/ol401265a

Reference yield: 73.0%

undecane-1,10-diol (10596-05-1) + 4-(hydroxymethyl)cyclohexan-1-ol (33893-85-5) → undecan-2-ol (1653-30-1,113666-64-1) + 4-hydroxymethyl-cyclohexanone (38580-68-6)

Guidance literature:

With NaBrO₃; acetic acid; In Ce;

upstream raw materials:

4-(hydroxymethyl)cyclohexan-1-ol

ethyl 4-oxocyclohexane-1-carboxylate

4-(hydroxymethyl)-1-<(trimethylsilyl)oxy>cyclohexene

(1,4-dioxaspiro[4.5]dec-8-yl)methanol

Refernces

• 1、 -. "PYRAZOLE AMIDE DERIVATIVE". . . Retrieved 2015/09/28.
• 2、 Wauters, Iris,De Blieck, Ann,Muylaert, Koen,Heugebaert, Thomas S. A.,Stevens, Christian V.. "Synthesis of Epibatidine Analogues Having a 2-Substituted 2-Azabicyclo[2.2.2]octane Skeleton". . p. 1296 - 1304. Retrieved 2015/10/05.