4,4-Difluorocyclohexanol Chemical Properties

Melting point:

60-65°C

Boiling point:

160.6±40.0 °C(Predicted)

Density 

1.15±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

14.14±0.40(Predicted)

form 

powder to lump

color 

White to Orange to Green

InChI

InChI=1S/C6H10F2O/c7-6(8)3-1-5(9)2-4-6/h5,9H,1-4H2

InChIKey

XTJZBCBHCPQASK-UHFFFAOYSA-N

SMILES

C1(O)CCC(F)(F)CC1

CAS DataBase Reference

22419-35-8

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

2906120000

4,4-Difluorocyclohexanol Usage And Synthesis

Chemical Properties

viscous liquid

Uses

4,?4-?Difluorocyclohexanol is a reagent used in the clearance of adenosine inhibitors of bacterial NAD+-dependent DNA ligase.

Synthesis

General procedure for the synthesis of 4,4-difluorocyclohexanol from 4,4-difluorocyclohexanone: Sodium borohydride (460 mg, 12.17 mmol) was added to a cold solution of 4,4-difluorocyclohexanone (907 mg, 6.76 mmol) in methanol (22 mL) under the conditions of an ice water bath. The reaction mixture was stirred for 5 minutes and then allowed to warm slowly to room temperature and continued stirring for 1 hour. Upon completion of the reaction, the reaction was quenched with water (11 mL) and stirred for 30 minutes. Subsequently, the solvent was removed by concentration on a rotary evaporator and the residue was partitioned between water (11 mL) and dichloromethane (10 mL). The aqueous layer was separated and extracted with dichloromethane (3 x 10 mL). All organic layers were combined, dried with anhydrous magnesium sulfate, filtered and the solvent was concentrated to give the target product 4,4-difluorocyclohexanol (839 mg, 91% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 4.03-3.82 (m, 1H), 2.26-1.98 (m, 2H), 1.98-1.64 (m, 6H), 1.43 (d, J = 3.6 Hz, 1H).

References

[1] Patent: WO2015/164520, 2015, A1. Location in patent: Page/Page column 63
[2] Patent: WO2016/196776, 2016, A2. Location in patent: Paragraph 001239
[3] Patent: EP2213675, 2010, A1. Location in patent: Page/Page column 41
[4] Patent: US2015/94328, 2015, A1. Location in patent: Paragraph 0427-0429
[5] Patent: WO2015/49574, 2015, A1. Location in patent: Page/Page column 49; 50

4,4-Difluorocyclohexanol(22419-35-8)Related Product Information

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