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269697

Sigma-Aldrich

Ethyl 4,4,4-trifluorocrotonate

98%

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Synonym(s):
Ethyl 4,4,4-trifluoro-2-butenoate
Linear Formula:
CF3CH=CHCO2C2H5
CAS Number:
Molecular Weight:
168.11
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.)

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

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1 of 4

This Item
129712168092443700
Ethyl 4,4,4-trifluorocrotonate 98%

269697

Ethyl 4,4,4-trifluorocrotonate

Methyl 3-aminocrotonate 97%

129712

Methyl 3-aminocrotonate

Ethyl 2-oxocyclopentanecarboxylate 95%

168092

Ethyl 2-oxocyclopentanecarboxylate

Ethyl 4,4,4-trifluorobutyrate ≥98%

443700

Ethyl 4,4,4-trifluorobutyrate

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

form

liquid

form

solid

form

-

form

liquid

refractive index

n20/D 1.3601 (lit.)

refractive index

-

refractive index

n20/D 1.452 (lit.)

refractive index

n20/D 1.3516 (lit.)

bp

114-115 °C (lit.)

bp

-

bp

102-104 °C/11 mmHg (lit.)

bp

127 °C (lit.)

density

1.125 g/mL at 25 °C (lit.)

density

-

density

1.054 g/mL at 25 °C (lit.)

density

1.16 g/mL at 25 °C (lit.)

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

78.8 °F - closed cup

flash_point_c

26 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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An efficient asymmetric synthesis of (2S,3S)-3-trifluoromethylpyroglutamic acid.
Tetrahedron Letters, 38(27), 4903-4904 (1997)
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)

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