Ethyl trifluoropyruvate Property

Boiling point:

42 °C(lit.)

Density 

1.283 g/mL at 25 °C (lit.)

vapor pressure 

12.49hPa at 25℃

refractive index 

n20/D 1.341(lit.)

Flash point:

88 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

Miscible with dichloromethane.

form 

Liquid

color 

Clear colorless to pale yellow

BRN 

2087388

Stability:

Moisture Sensitive

InChIKey

KJHQVUNUOIEYSV-UHFFFAOYSA-N

LogP

-0.05

CAS DataBase Reference

13081-18-0(CAS DataBase Reference)

Safety

Hazard Codes 

Xn,C,Xi

Risk Statements 

10-22-36/37/38

Safety Statements 

26-37/39-16

RIDADR 

UN 3272 3/PG 3

WGK Germany 

3

Hazard Note 

Corrosive

HazardClass 

3

PackingGroup 

III

HS Code 

29183000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H226Flammable liquid and vapour

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Ethyl trifluoropyruvate Chemical Properties,Usage,Production

Chemical Properties

Clear pale yellow liquid

Uses

Ethyl trifluoropyruvate acts as a building block in synthetic chemistry for the synthesis of fluorine containing compounds. It is also used as a reagent for the preparation of potential biologically active compounds like highly enantioselective organocatalytic hydroxyalkylation of indoles.

Uses

Ethyl 3,3,3-trifluoropyruvate may be used in the preparation of N-heteroaryl(trifluoromethyl)hydroxyalkanoic acid esters.

Uses

Ethyl Trifluoropyruvate is used as a reagent in the preparation of potential biologically active compounds such as in the highly enantioselective organocatalytic hydroxyalkylation of indoles .

General Description

Ethyl 3,3,3-trifluoropyruvate is a trifluoromethylated compound. Enantioselective Friedel–Crafts alkylation of simple phenols and indoles with ethyl 3,3,3-trifluoropyruvate under different reaction conditions have been reported.

Synthesis

To 58 mL (1.0 mL/mmol) of acetonitrile, 10 g (58 mmol, 1.0 eq) of ethyl 3,3,3-trifluorolactate was added and dissolved therein.Furthermore, 11 g (67 mmol, 1.2 eq) of NaClO.5H2O was added, followed by stirring at 20° C. for 30 minutes.As the reaction-terminated liquid was analyzed by 19F-NMR, conversion was 100%, and selectivity was 98%.To the reaction-terminated liquid, 0.38 g (1.5 mmol, 0.026 eq) of sodium thiosulfate pentahydrate was added, followed by stirring, thereby quenching the remaining oxidation agent.Furthermore, 0.33 g (3.9 mmol, 0.067 eq) of sodium hydrogencarbonate and 10 g (70 mmol, 1.2 eq) of sodium sulfate were added, followed by stirring and then removing solid matter by filtration.As the filtrate was quantified with internal standard method (internal standard substance: α,α,α-trifluorotoluene) by 19F-NMR, Ethyl trifluoropyruvate was contained by 56 mmol (quantitative yield: 97%).By a simple distillation (up to 48° C./0.5 kPa) of the filtrate, 7.6 g of Ethyl trifluoropyruvate was obtained. 19F-NMR purity was 99% (40 mmol), and the total yield was 69%.