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Merck
CN

E50205

Ethyl 4,4,4-trifluoroacetoacetate

99%

Synonym(s):

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

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About This Item

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

Key Documents

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Product Name

Ethyl 4,4,4-trifluoroacetoacetate, 99%

InChI key

OCJKUQIPRNZDTK-UHFFFAOYSA-N

InChI

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

SMILES string

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

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.)

Quality Level

100

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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
GHS02,GHS07

signalword

Warning

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SDBB1543
STBL1665
STBK9375
STBF5698V
STBD1917V

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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)
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)

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