ETHYL 4,4,4-TRIFLUORO-2-BUTYNOATE 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

• Language:English Provider:SigmaAldrich

ETHYL 4,4,4-TRIFLUORO-2-BUTYNOATE 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

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(79424-03-6)Related Product Information

• 1,1,1-TRIFLUORO-2-BUTYNE
• Ethyl propiolate
• 2-Butynoic acid
• Ethyl 2-butynoate
• ETHYL 4,4,4-TRIFLUORO-2-BUTYNOATE
• 3,3,3-TRIFLUOROPROPYNE