3,5-BIS(TRIFLUOROMETHYL)PHENYLACETYLENE Chemical Properties

Boiling point:

147-148 °C (lit.)

Density 

1.346 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.4230(lit.)

Flash point:

112 °F

storage temp. 

2-8°C

form 

clear liquid

color 

Colorless to Light yellow to Light orange

InChI

InChI=1S/C10H4F6/c1-2-6-3-7(9(11,12)13)5-8(4-6)10(14,15)16/h1,3-5H

InChIKey

MAHIBRPXUPUAIF-UHFFFAOYSA-N

SMILES

C1(C#C)=CC(C(F)(F)F)=CC(C(F)(F)F)=C1

CAS DataBase Reference

88444-81-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36/37/38

Safety Statements 

16-26-36

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

3

HS Code 

29039990

MSDS

• Language:English Provider:SigmaAldrich

3,5-BIS(TRIFLUOROMETHYL)PHENYLACETYLENE Usage And Synthesis

Uses

3,5-Bis(trifluoromethyl)phenylacetylene is a useful research chemical.

Chemical Properties

Yellow liquid

Synthesis

General procedure for the synthesis of 3,5-bis(trifluoromethyl)phenylethynyltrimethylsilane from (3,5-bis(trifluoromethyl)phenylethynyl)trimethylsilane: To a mixed solution of 2-[3,5-bis(trifluoromethyl)phenyl]ethynyltrimethylsilane (83.1g, 267.7mmol) in methanol (70mL) and chloroform (70mL) was added potassium carbonate (7.4g, 53.5 mmol), followed by stirring the reaction mixture at room temperature overnight. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. Water was added to the residue and extracted with ether. The organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. After filtration to remove the desiccant, the filtrate was concentrated under reduced pressure to give the crude product. The crude product was further purified by reduced pressure distillation (82 °C, 100 mbar) to afford 3,5-bis(trifluoromethyl)phenylacetylene (48.7 g, 76% yield) as a colorless oil. The structure of the product was confirmed by 1H NMR (CDCl3): δ 7.92 (2H, s), 7.84 (1H, s), 3.26 (1H, s).

References

[1] Dalton Transactions, 2012, vol. 41, # 3, p. 839 - 849
[2] Patent: US2018/290986, 2018, A1. Location in patent: Paragraph 0230; 0231
[3] Journal of Organic Chemistry, 1993, vol. 58, # 24, p. 6614 - 6619
[4] Chemical Communications, 2008, # 19, p. 2203 - 2205
[5] Journal of Materials Chemistry C, 2017, vol. 5, # 31, p. 7977 - 7984

3,5-BIS(TRIFLUOROMETHYL)PHENYLACETYLENE(88444-81-9)Related Product Information

• 4'-TRIFLUOROMETHYLPHENYL ACETYLENE
• Phenylacetylene
• 3,5-BIS(TRIFLUOROMETHYL)PHENYLACETYLENE
• 2,5-bis(trifluoromethyl)phenylacetylene
• (3,5-BIS(TRIFLUOROMETHYL)PHENYLETHYNYL)&
• BIS[3,5-BIS(TRIFLUOROMETHYL)PHENYL]ACETYLENE
• 3,5-BIS(TRIFLUOROMETHYL)DIPHENYLACETYLENE
• FLUPROPADINE
• (3-[3,5-DI(TRIFLUOROMETHYL)PHENYL]PROP-2-YNYL)(TRIETHYL)AMMONIUM BROMIDE
• N-(3-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]-1,1-DIMETHYLPROP-2-YNYL)-2-CHLOROACETAMIDE
• 3-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]PROP-2-YN-1-OL
• 3-[3,5-DI(TRIFLUOROMETHYL)PHENYL]PROP-2-YNYL N-(1,2,2-TRICHLOROVINYL)CARBAMATE
• 4-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]-3-BUTYN-2-OL
• 3-[3,5-DI(TRIFLUOROMETHYL)PHENYL]PROP-2-YNYL 2-CHLOROACETATE
• 1-(3-BROMOPROP-1-YNYL)-3,5-DI(TRIFLUOROMETHYL)BENZENE
• 1-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-3-HYDROXY-3-METHYL-1-BUTYNE