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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:
383-63-1
Molecular Weight:
142.08
Beilstein/REAXYS Number:
1761411
EC Number:
206-851-6
MDL number:
MFCD00000419
UNSPSC Code:
12352100
PubChem Substance ID:
24894596
NACRES:
NA.22

Quality Level

200

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.

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

30.2 °F - closed cup

flash_point_c

-1 °C - closed cup

ppe

Eyeshields, Faceshields, 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)
Highly selective trifluoroacetic ester/ketone metathesis: an efficient approach to trifluoromethyl ketones and esters
Zhou Y, et al.
Tetrahedron, 70(31), 4668-4674 (2014)
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
Non-defluorinative electrochemical silylation of ethyl trifluoroacetate: a practical synthesis of trifluoroacetyltrimethylsilane via its ethyltrimethylsilyl ketal
Bordeau M, et al.
Tetrahedron Letters, 44(19), 3741-3744 (2003)
Synthesis of substituted 3-trifluoromethylbenzo[b]thiophenes
Owton WM
Tetrahedron Letters, 44(38), 7147-7149 (2003)
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