4-(HYDROXYMETHYL)CYCLOHEXANONE Chemical Properties

Boiling point:

239.8±13.0 °C(Predicted)

Density 

1.054±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

solid

pka

14.85±0.10(Predicted)

InChI

InChI=1S/C7H12O2/c8-5-6-1-3-7(9)4-2-6/h6,8H,1-5H2

InChIKey

KHMBXNKCMNGLKG-UHFFFAOYSA-N

SMILES

C1(=O)CCC(CO)CC1

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41

Safety Statements 

26-39

HS Code 

2914500090

4-(HYDROXYMETHYL)CYCLOHEXANONE Usage And Synthesis

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.

Synthesis Reference(s)

Tetrahedron Letters, 19, p. 2771, 1978 DOI: 10.1016/S0040-4039(01)94858-0

Synthesis

Example 5: Ce(IV)/PFCP (50 mg, 0.027 mmol) and NaBrO3 (200 mg) were dispersed and dissolved in acetic acid. Subsequently, 1,10-undecanediol (1.0 mmol) and 4-hydroxymethylcyclohexanol (1.0 mmol) were added, respectively. The reaction mixture was heated at 55°C for 3 hours. Upon completion of the reaction, the products were purified by column chromatography to afford 10-undecan-1-ol (154 mg, 82% yield) and 4-hydroxymethylcyclohexanone (93 mg, 73% yield).

References

[1] Patent: US4617153, 1986, A

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