Skip to Content
Merck
CN
All Photos(1)

Documents

Safety Information

E50205

Sigma-Aldrich

Ethyl 4,4,4-trifluoroacetoacetate

99%

Synonym(s):

ETFAA, Ethyl 3-oxo-4,4,4-trifluorobutyrate

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
CF3COCH2CO2C2H5
CAS Number:
372-31-6
Molecular Weight:
184.11
Beilstein:
608353
EC Number:
206-750-7
MDL number:
MFCD00000424
UNSPSC Code:
12352100
PubChem Substance ID:
24894598
NACRES:
NA.22

Quality Level

100

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H302,H412

Precautionary Statements

P210 - P273 - P301 + P312 + P330

Hazard Classifications

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

WGK

WGK 2

Flash Point(F)

100.4 °F

Flash Point(C)

38 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Straightforward Synthesis of Novel Enantiopure α-Trifluoromethylated Azetidine 2-Carboxylic Acid and Homoserines.
Lensen N, et al.
Organic Letters, 17(2), 342-345 (2015)
Concise synthesis of enantiopure (S)-and (R)-α-trifluoromethyl aspartic acid and α-trifluoromethyl serine from chiral trifluoromethyl oxazolidines (Fox) via a Strecker-type reaction.
Simon J, et al.
Tetrahedron Asymmetry, 22(3), 309-314 (2011)
Ethyl-4, 4, 4-trifluoroacetoacetate (ETFAA), a powerful building block for enantiopure chirons in trifluoromethyl-β-amino acid series.
Michaut V, et al.
Journal of Fluorine Chemistry, 128(8), 889-895 (2007)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service