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Key Documents

269697

Sigma-Aldrich

Ethyl 4,4,4-trifluorocrotonate

98%

Synonym(s):

Ethyl 4,4,4-trifluoro-2-butenoate

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About This Item

Linear Formula:
CF3CH=CHCO2C2H5
CAS Number:
Molecular Weight:
168.11
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.3601 (lit.)

bp

114-115 °C (lit.)

density

1.125 g/mL at 25 °C (lit.)

functional group

ester

SMILES string

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

InChI

1S/C6H7F3O2/c1-2-11-5(10)3-4-6(7,8)9/h3-4H,2H2,1H3/b4-3+

InChI key

ZKRJCMKLCDWROR-ONEGZZNKSA-N

General description

The Michael reaction between ethyl 4,4,4-trifluorocrotonate and a Ni(II) complex of the Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone was studied.

Application

Ethyl 4,4,4-trifluorocrotonate was used in the synthesis of (2S,3S)-3-methyl- and (2S,3S)-3-trifluoromethylpyroglutamic acid. It undergoes diastereoselective Michael addition reaction with ethyl crotonate.

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

78.8 °F - closed cup

Flash Point(C)

26 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Stereochemically defined C-substituted glutamic acids and their derivatives. 1. An efficient asymmetric synthesis of (2S, 3S)-3-methyl-and-3-trifluoromethylpyroglutamic acids.
Soloshonok VA, et al.
Tetrahedron, 55(41), 12031-12044 (1999)
An efficient asymmetric synthesis of (2S,3S)-3-trifluoromethylpyroglutamic acid.
Tetrahedron Letters, 38(27), 4903-4904 (1997)

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