3,3-Difluorocyclobutanecarboxylic acid Chemical Properties

Melting point:

51.0 to 55.0 °C

Boiling point:

205 °C

Density 

1.37

Flash point:

78 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

3.63±0.40(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C5H6F2O2/c6-5(7)1-3(2-5)4(8)9/h3H,1-2H2,(H,8,9)

InChIKey

PLRCVBKYFLWAAT-UHFFFAOYSA-N

SMILES

C1(C(O)=O)CC(F)(F)C1

Safety Information

RIDADR 

UN 3261 8/PG III

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

2916200090

3,3-Difluorocyclobutanecarboxylic acid Usage And Synthesis

Uses

3,3-Difluorocyclobutane carboxylic acid is used as an organic and pharmaceutical intermediate.

Synthesis Reference(s)

Synthetic Communications, 35, p. 657, 2005 DOI: 10.1081/SCC-200050350

Synthesis

General procedure for the synthesis of 3,3-difluorocyclobutanecarboxylic acid from benzyl ester of 3,3-difluorocyclobutanecarboxylate: benzyl ester of 3,3-difluorocyclobutanecarboxylic acid (0.84 g, 3.72 mmol) was dissolved in ethanol (40 mL), and about 0.02 g of palladium/activated carbon catalyst was added. The reaction mixture was stirred at room temperature for 12 hours in a hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by filtration through a diatomaceous earth pad. The filtrate was concentrated and dried under vacuum to afford the target product 3,3-difluorocyclobutanecarboxylic acid (0.46 g, 90% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 3.16-2.55 (m, 5H).

References

[1] Patent: WO2013/107405, 2013, A1. Location in patent: Page/Page column 42
[2] Patent: US2015/87600, 2015, A1. Location in patent: Page/Page column
[3] Patent: EP3290418, 2018, A1. Location in patent: Paragraph 0172; 0181
[4] Patent: US9273058, 2016, B2. Location in patent: Page/Page column 337; 338
[5] Patent: WO2007/47625, 2007, A2. Location in patent: Page/Page column 24

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