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E50205

Sigma-Aldrich

Ethyl 4,4,4-trifluoroacetoacetate

99%

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Synonym(s):
ETFAA, Ethyl 3-oxo-4,4,4-trifluorobutyrate
Linear Formula:
CF3COCH2CO2C2H5
CAS Number:
Molecular Weight:
184.11
Beilstein/REAXYS Number:
608353
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

form

liquid

refractive index

n20/D 1.375 (lit.)

bp

129-130 °C (lit.)

density

1.259 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)CC(=O)C(F)(F)F

InChI

1S/C6H7F3O3/c1-2-12-5(11)3-4(10)6(7,8)9/h2-3H2,1H3

InChI key

OCJKUQIPRNZDTK-UHFFFAOYSA-N

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Application

Ethyl 4,4,4-trifluoroacetoacetate (ETFAA) is a general reagent to synthesize enantiopure trifluoromethyl-functionalized products. Applications include:
  • Synthesis of (S)- and (R)-α-trifluoromethyl-aspartic acid and α- trifluoromethyl-serine from chiral CF3-oxazolidines, which is derived from ETFAA.
  • Enantiopure synthesis of trifluoromethyl-β-amino acid derivatives.
  • Synthesis of (2R)-2-trifluoromethyl-2-carboxyazetidine, (R)- and (S)-trifluoromethylhomoserines from oxazolidine intermediate obtained by condensing (R)-phenylglycinol with ETFAA.

pictograms

FlameExclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

100.4 °F - closed cup

flash_point_c

38 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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