407771

Sigma-Aldrich

4-Ethoxy-1,1,1-trifluoro-3-buten-2-one

contains 0.5% BHT as stabilizer, technical grade

Linear Formula:
C2H5OCH=CHCOCF3
CAS Number:
Molecular Weight:
168.11
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

grade

technical grade

Quality Level

contains

0.5% BHT as stabilizer

refractive index

n20/D 1.406 (lit.)

bp

51-53 °C/12 mmHg (lit.)

density

1.18 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCO\C=C\C(=O)C(F)(F)F

InChI

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

InChI key

YKYIFUROKBDHCY-ONEGZZNKSA-N

Related Categories

General description

4-Ethoxy-1,1,1-trifluoro-3-buten-2-one reacts with phenylmagnesium bromide to afford ethoxy group substitution products, while it reacts with organozinc compounds to yield products arising from 1,2-addition to the carbonyl group. 4-Ethoxy-1,1,1-trifluoro-3-buten-2-one on heating with triethyl phosphite affords 4+2 cycloaddition product, 2,2,2-triethoxy 2,3-dihydro-3-ethoxy-5-trifluoromethyl-1,2λ5-oxaphospholene, which on hydrolysis affords a 2-oxo-2-hydroxy-2, 3-dihydro-3-hydroxy 5-trifluoromethyl-1,2λ5-oxaphospholen. It reacts with amino to give the N-protected amino acids, which is useful for the peptide synthesis.

Application

4-Ethoxy-1,1,1-trifluoro-3-buten-2-one may be used in the synthesis of 4-dialkylamino-1,1,1-trifluorobut-3-ene-2-ones. It may be used for the synthesis of β-alkyl- or dialkylamino substituted enones bearing a CF3 group.

Packaging

5 g in glass bottle

Pictograms

FlameHealth hazard

Signal Word

Warning

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xn

Risk Statement

10-40

Safety Statement

36/37

RIDADR

UN1224 - class 3 - PG 3 - Ketones, liquid, n.o.s., HI: all

WGK Germany

WGK 3

Flash Point(F)

125.6 °F - closed cup

Flash Point(C)

52 °C - closed cup

The interaction of 4-ethoxy-1, 1, 1-trifluoro-3-buten-2-one with C-nucleophiles-organo-magnesium and-zinc compounds
Gorbunova MG, et al.
Journal of Fluorine Chemistry, 65(1), 25-28 (1993)
The interaction of 4-ethoxy-1, 1, 1-trifluoro-3-buten-2-one with triethyl phosphite.
Gerus II, et al.
Journal of Fluorine Chemistry, 90(1), 1-3 (1998)
4-Ethoxy-1, 1, 1-trifluoro-3-buten-2one as a new protecting reagent in peptide synthesis.
Gorbunova MG, et al.
Synthesis, 3, 207-209 (1991)
Preparation of α, β-unsaturated ketones bearing a trifluoromethyl group and their application in organic synthesis.
Nenajdenko VG, et al.
Molecules (Basel), 2(12), 186-232 (1997)
Synthesis of Trifluoromethylpyrroles and Related Heterocycles from 4-Ethyloxy-1, 1, 1-trifluorobut-3-ene-2-one.
Andrew RJ and Mellor JM.
Tetrahedron, 56(37), 7267-7272 (2000)

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