4,4-Difluorocyclohexanecarboxylic acid Chemical Properties

Melting point:

103-107 °C

Boiling point:

241.1±40.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol

pka

4.06±0.10(Predicted)

form 

Solid

color 

White

InChI

InChI=1S/C7H10F2O2/c8-7(9)3-1-5(2-4-7)6(10)11/h5H,1-4H2,(H,10,11)

InChIKey

HYIUDFLDFSIXTR-UHFFFAOYSA-N

SMILES

C1(C(O)=O)CCC(F)(F)CC1

CAS DataBase Reference

122665-97-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29161900

4,4-Difluorocyclohexanecarboxylic acid Usage And Synthesis

Chemical Properties

4,4-Difluorocyclohexanecarboxylic acid is White Solid

Uses

4,4-Difluorocyclohexanecarboxylic acid is a di-substituted cyclohexane carboxylic acids used in the synthesis of macrolide antibiotics.

Synthesis

The general procedure for the synthesis of 4,4-difluorocyclohexanecarboxylic acid from ethyl 4,4-difluorocyclohexanecarboxylate was as follows: ethyl 4,4-difluorocyclohexanecarboxylate (0.385 g, 2.003 mmol) was dissolved in THF (12 mL), and H2O (6 mL) was added, followed by lithium hydroxide monohydrate (0.420 g, 10.02 mmol). The reaction mixture was stirred vigorously at room temperature overnight. Upon completion of the reaction, the mixture was diluted with EtOAc and the pH was adjusted to 4 with 1 M HCl. The organic and aqueous layers were separated, and the aqueous layer was then extracted with EtOAc (1 time). The organic phases were combined, washed with brine, dried over MgSO4 and concentrated to dryness to give 4,4-difluorocyclohexanecarboxylic acid (318 mg, 97% yield) as a white solid.1H NMR (400 MHz, DMSO-d6): δ 12.28 (s, 1H), 2.40 (m, 1H), 2.02-1.75 (m, 6H), 1.59 (m, 2H) .

References

[1] Patent: US2014/275080, 2014, A1. Location in patent: Paragraph 0428
[2] Patent: WO2013/13188, 2013, A1. Location in patent: Paragraph 00313; 00314
[3] Patent: US9416132, 2016, B2. Location in patent: Page/Page column 134; 135
[4] Organic Letters, 2018, vol. 20, # 16, p. 4959 - 4963
[5] Patent: US2008/146605, 2008, A1. Location in patent: Page/Page column 39-40

4,4-Difluorocyclohexanecarboxylic acid(122665-97-8)Related Product Information

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