Ethyl 4,4,4-trifluoro-2-butynoate

Product NameEthyl 4,4,4-trifluoro-2-butynoate
CAS79424-03-6
MFC6H5F3O2
MW166.1
EINECS
MOL File79424-03-6.mol

Chemical Properties

Boiling point	96-98 °C(lit.)
Density	1.162 g/mL at 25 °C(lit.)
refractive index	n20/D 1.350(lit.)
Flash point	43 °F
storage temp.	Inert atmosphere,2-8°C
solubility	Chloroform (Slightly), Methanol (Slightly)
form	Liquid
color	Clear colorless
Specific Gravity	1.162
Water Solubility	Soluble in water (partly).
BRN	3539414
Stability	Volatile
InChI	InChI=1S/C6H5F3O2/c1-2-11-5(10)3-4-6(7,8)9/h2H2,1H3
InChIKey	SFDRHPQGYUYYNX-UHFFFAOYSA-N
SMILES	C(OCC)(=O)C#CC(F)(F)F
CAS DataBase Reference	79424-03-6

Safety Information

Hazard Codes	F,Xi
Risk Statements	11-36/37/38
Safety Statements	16-26-36/37/39
RIDADR	UN 3272 3/PG 2
WGK Germany	3
F	19
Hazard Note	Irritant/Highly Flammable
HazardClass	3.1
PackingGroup	II
HS Code	29161900
Storage Class	3 - Flammable liquids
Hazard Classifications	Eye Irrit. 2 Flam. Liq. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

Clear colorless liquid

Uses

Ethyl 4,4,4-trifluoro-2-butynoate is the suitable reagent used to investigate the regioselectivity of the insertion reaction with cyclometalated iridium and rhodium complexes. It may be used in the preparation of ethyl (Z)-3-iodo-4,4,4-trifluoro-2-butenoate.

General Description

Ethyl 4,4,4-trifluoro-2-butynoate is an unsymmetrical internal alkyne.

Synthesis

ETHYL 4,4,4-TRIFLUORO-2-(TRIPHENYLPHOSPHORANYLIDENE)ACETOACETATE

83961-56-2

79424-03-6

General procedure for the synthesis of ethyl 4,4,4-trifluoro-2-butynoate from ethyl 4,4,4-trifluoro-2-(triphenylphosphoranylidene)acetoacetate: 1. Preparation of reaction materials: ethyl 4,4,4-trifluoro-2-(triphenylphosphoranylidene)acetoacetate (270 g, 617 mmol) and potassium carbonate (54 g, 490 mmol) were weighed. 2. Reaction conditions: The above mixture was heated gradually from 160 °C to 225 °C over a period of 3 h and the reaction was carried out under reduced pressure (mbar vacuum). 3. Isolation of product: Ethyl 4,4,4-trifluoro-2-butynoate was collected by distillation and recovered in a cold trap. 4. Characterization of product: The product was obtained as a shallow product. 4. Characterization of the product: Ethyl 4,4,4-trifluoro-2-butynoate was obtained as a light yellow oil (85 g, 83% yield), the structure of which was confirmed by ES/MS, m/e 167 (M+1).

References

[1] Synlett, 2002, # 8, p. 1265 - 1268
[2] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 270 - 277
[3] Patent: WO2007/140174, 2007, A2. Location in patent: Page/Page column 45-46
[4] Organic Syntheses, 1992, vol. 70, p. 246 - 246
[5] Journal of Fluorine Chemistry, 1995, vol. 70, # 1, p. 59 - 70

Ethyl 4,4,4-trifluoro-2-butynoate

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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