4,4,4-Trifluorobutyric acid Chemical Properties

Melting point:

25-31 °C

Boiling point:

166-167°C

Density 

>1.0

refractive index 

n20/D 1.351

Flash point:

166-167°C

storage temp. 

2-8°C

pka

pK1:4.16 (25°C)

form 

powder to lump

color 

White to Almost white

Water Solubility 

Soluble in water.

InChI

InChI=1S/C4H5F3O2/c5-4(6,7)2-1-3(8)9/h1-2H2,(H,8,9)

InChIKey

WTUCTMYLCMVYEX-UHFFFAOYSA-N

SMILES

C(O)(=O)CCC(F)(F)F

CAS DataBase Reference

406-93-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

34-36

Safety Statements 

26-36/37/39-45-20

RIDADR 

3265

WGK Germany 

3

Hazard Note 

Corrosive

HazardClass 

8

PackingGroup 

II

HS Code 

29159000

MSDS

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4,4,4-Trifluorobutyric acid Usage And Synthesis

Chemical Properties

Colorless low melting solid

Uses

4,4,4-Trifluorobutyric acid is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 4403, 1989 DOI: 10.1016/S0040-4039(00)99372-9

Synthesis

General procedure for the synthesis of 4,4,4-trifluorobutyric acid from ethyl 4,4,4-trifluorobutyrate: a mixture of 123 g of potassium hydroxide, 900 mL of methanol, and 80 mL of water was slowly added to 160 g of ethyl 4,4,4-trifluorobutyrate under the cooling of an ice-water bath and stirring was maintained. The reaction mixture was continued to be stirred for 12 hours at room temperature. After completion of the reaction, the reaction solution was concentrated under reduced pressure to give a residue. The residue was partitioned between water and ether. The ether layer was separated and washed once with water; the aqueous layer was combined with the previously separated aqueous layer. To the combined aqueous layer, ice-cold 10% hydrochloric acid solution was added and the pH adjusted to 1. Subsequently, the acidic aqueous solution was extracted three times with ether. All ether layer extracts were combined, washed twice with brine and dried with anhydrous magnesium sulfate. After filtration, the filtrate was evaporated under reduced pressure to give 131 g of 4,4,4-trifluorobutyric acid in 98% yield.1H-NMR (CDCl3, internal standard TMS) δ values (ppm): 2.52 (m, 2H), 2.67 (t, 2H).

References

[1] Patent: US5550258, 1996, A
[2] Patent: US5653990, 1997, A
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 9, p. 1282 - 1297
[4] Patent: US5280125, 1994, A
[5] Patent: US5286740, 1994, A

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