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

Melting point:

-30℃

Boiling point:

51-53 °C/12 mmHg (lit.)

Density 

1.18 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.406(lit.)

Flash point:

125 °F

storage temp. 

2-8°C

solubility 

soluble in Chloroform, Methanol

form 

Liquid

color 

Colorless to yellow

Sensitive 

Moisture Sensitive

InChI

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

InChIKey

YKYIFUROKBDHCY-ONEGZZNKSA-N

SMILES

C(F)(F)(F)C(=O)C=COCC

LogP

1.414 (est)

CAS DataBase Reference

17129-06-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,F

Risk Statements 

10-40

Safety Statements 

16-36-36/37

RIDADR 

UN 1224 3/PG 3

WGK Germany 

3

Hazard Note 

Flammable/Harmful

HazardClass 

3

PackingGroup 

III

HS Code 

29147000

Storage Class

3 - Flammable liquids

Hazard Classifications

Aquatic Chronic 3
Carc. 2
Flam. Liq. 3

MSDS

• Language:English Provider:SigmaAldrich

4-Ethoxy-1,1,1-trifluoro-3-buten-2-one Usage And Synthesis

Chemical Properties

light yellow liquid

Uses

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.

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.

Synthesis

Example 1 Preparation of 4-ethoxy-1,1,1-trifluoro-3-buten-2-one Ethyl vinyl ether (60 g) and triethylamine (28 g) were placed in an autoclave. The reaction vessel was cooled to 10°C to 15°C with continuous stirring. Trifluoroacetyl fluoride (99 g) was added in batches through an impregnation line of stainless steel cylinders at a temperature of 30°C to 40°C and a pressure of 5 to 10 kg/cm2 . After the addition was completed, the reaction mixture was continued to be stirred for 30 min until the reactor pressure was reduced to 0.25 to 0.5 kg/cm2. Excess trifluoroacetyl fluoride was removed by distillation under reduced pressure, followed by washing the reaction mixture with water. The organic layer was separated and concentrated by decompression to give the title product 4-ethoxy-1,1,1-trifluoro-3-buten-2-one. Yield: 86.2%; purity: 98.2%.

References

[1] Patent: WO2015/11728, 2015, A1. Location in patent: Page/Page column 7

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