269697
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
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Assay:
98%
Form:
liquid
InChI
1S/C6H7F3O2/c1-2-11-5(10)3-4-6(7,8)9/h3-4H,2H2,1H3/b4-3+
SMILES string
CCOC(=O)\C=C\C(F)(F)F
InChI key
ZKRJCMKLCDWROR-ONEGZZNKSA-N
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, fluoro
Quality Level
Related Categories
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.
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Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 3 - STOT SE 3
target_organs
Respiratory system
Storage Class
3 - Flammable liquids
wgk
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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