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E50000

Sigma-Aldrich

Ethyl trifluoroacetate

99%

Synonym(s):

Trifluoroacetic acid ethyl ester

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About This Item

Linear Formula:
CF3COOC2H5
CAS Number:
Molecular Weight:
142.08
Beilstein:
1761411
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

form

liquid

refractive index

n20/D 1.307 (lit.)

bp

60-62 °C (lit.)

density

1.194 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/C4H5F3O2/c1-2-9-3(8)4(5,6)7/h2H2,1H3

InChI key

STSCVKRWJPWALQ-UHFFFAOYSA-N

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Application

Ethyl trifluoroacetate can be used:
  • To synthesize cyclopentenones or furans containing trifluoromethyl group from aromatic ynones.
  • In the selective trifluoroacetylation of anilines catalyzed by 4-dimethylaminopyridine.
  • As a starting material in the two-step electrosynthesis of trifluoroacetyltrimethylsilane (CF3COSiMe3).
  • In the preparation of trifluoromethyl ketones via trifluoroacetic ester/ketone metathesis with alkyl aryl ketones.
  • To synthesize o-fluorinated trifluoro acetophenones from substituted fluorobenzene.

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

30.2 °F - closed cup

Flash Point(C)

-1 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

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Synthesis of 4-(Trifluoromethyl) cyclopentenones and 2-(Trifluoromethyl) furans by Reductive Trifluoroacetylation of Ynones
Zhang T and Maekawa H
Organic Letters, 19(24), 6602-6605 (2017)
Xiaoyan Li et al.
Preparative biochemistry & biotechnology, 47(9), 852-859 (2016-05-26)
Uridine 5'-diphosphate N-acetylglucosamine (UDP-GlcNAc) is a natural UDP-monosaccharide donor for bacterial glycosyltransferases, while uridine 5'-diphosphate N-trifluoacetyl glucosamine (UDP-GlcNTFA) is its synthetic mimic. The chemoenzymatic synthesis of UDP-GlcNAc and UDP-GlcNTFA was attempted by three recombinant enzymes. Recombinant N-acetylhexosamine 1-kinase was used
Qi Zhang et al.
Journal of biophotonics, 11(6), e201700339-e201700339 (2018-01-18)
Targeting cyclooxygenase-2 (COX-2) for molecular imaging is an attractive approach applicable for its overexpression in inflammation and many malignancies. Herein, for monitoring COX-2, we synthesize a specific COX-2 probe celecoxib-MPA probe (CMP), based on celecoxib and a water-soluble near-infrared dye
Heike Gerhardt et al.
Journal of chromatography. A, 1428, 280-291 (2015-06-20)
A panel of methods of general suitability for complete structural elucidation of the stereochemistry of cyclopeptides, depsipeptides and lipopeptides is presented and described in detail. The suitability of the proposed methods was exemplified on the lipopeptide poaeamide from Pseudomonas poae.
Highly selective trifluoroacetic ester/ketone metathesis: an efficient approach to trifluoromethyl ketones and esters
Zhou Y, et al.
Tetrahedron, 70(31), 4668-4674 (2014)

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