ChemicalBook Product Catalog Organic Chemistry Organic fluorine compound 4-Ethoxy-1,1,1-trifluoro-3-buten-2-one

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

Product Name4-Ethoxy-1,1,1-trifluoro-3-buten-2-one
CAS17129-06-5
MFC6H7F3O2
MW168.11
EINECS629-004-6
MOL File17129-06-5.mol

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

Provider	Language
SigmaAldrich	English

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

354-34-7

109-92-2

1-Ethoxy-3-trifluoromethyl-1,3-butadiene

59938-06-6

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

Preparation Products And Raw materials

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