ETHYL 3,3,3-TRIFLUOROPROPIONATE Chemical Properties

Melting point:

109 °C

Boiling point:

50°C 12mm

Density 

1.192

refractive index 

1.3912

Flash point:

8℃

storage temp. 

2-8°C

solubility 

Chloroform (Sparingly), Ethyl Acetate (Soluble)

form 

Oil

color 

Colourless

InChI

InChI=1S/C5H7F3O2/c1-2-10-4(9)3-5(6,7)8/h2-3H2,1H3

InChIKey

FMDMKDPUFQNVSH-UHFFFAOYSA-N

SMILES

C(OCC)(=O)CC(F)(F)F

Safety Information

Hazard Codes 

F,Xi

Risk Statements 

10

Safety Statements 

16-24/25

RIDADR 

3272

Hazard Note 

Flammable

HazardClass 

IRRITANT, FLAMMABLE

HS Code 

29159000

ETHYL 3,3,3-TRIFLUOROPROPIONATE Usage And Synthesis

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 7689, 1991 DOI: 10.1016/0040-4039(91)80566-O

Synthesis

4.4 General procedure for the preparation of ethyl 3,3,3-trifluoropropionate: (1) To a stirred suspension of potassium ethoxide (KOEt, 5.0 g, 59.4 mmol) in ether (Et2O, 200 mL), a solution of 2,2,3-tribromo-1,1,1-trifluoropropane (7, 6.0 g, 17.9 mmol) in ether (Et2O, 50 mL) was slowly added dropwise. The reaction mixture was stirred at room temperature for 15 min. Subsequently, the reaction was quenched with 1 M aqueous hydrochloric acid (50 mL) and stirring was continued for 30 min. The aqueous layer was separated and extracted with ether (50 mL × 3) and the combined organic phases were washed with brine (40 mL) and dried with anhydrous magnesium sulfate (MgSO4). The solvent was removed by concentration under reduced pressure to give the crude product. Purification of the crude product by distillation afforded ethyl 3,3,3-trifluoropropionate (1, 2.0 g, 72%) as a colorless oil with a boiling point of 106°C (760 mmHg). Product characterization data: IR (pure): 2989, 1747, 1384, 1360, 1267, 1216, 1110, 1026, 929, 836, 755, 653 cm-1. 1H NMR (400 MHz, CDCl3): δ 4.24 (q, J = 7.2 Hz, 2H), 3.17 (q, J = 10.1 Hz, 2H), 1.30 (t, J = 7.2 Hz, 3H). 13C NMR (100 MHz, CDCl3): δ 164.1 (q, JCF = 4.1 Hz, 1C), 123.4 (q, JCF = 274.5 Hz, 1C), 61.7 (1C), 39.5 (q, JCF = 30.8 Hz, 1C), 13.8 (1C). 19F NMR (376 MHz, CDCl3): δ -64.8 (t, JHF = 10.1 Hz, 3F). EI-MS m/z (relative abundance): 156 [M]+ (2.4), 141 [M-Me]+ (1.4), 129 [M+2H-Et]+ (8.2), 111 [M-OEt]+ (100), 91 [CF2CHCO]+ (12.9), 83 [CF3CH2]+ (15.7), 69 [CF3]+ (7.5) , 45 [EtO]+ (41.4).

References

[1] Journal of Fluorine Chemistry, 2014, vol. 167, p. 135 - 138

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