4-(TERT-BUTYL)PHENYLACETYLENE

4-(TERT-BUTYL)PHENYLACETYLENE Property

Boiling point:

70 °C2 mm Hg(lit.)

Density 

0.877 g/mL at 25 °C(lit.)

refractive index 

1.528-1.53

Flash point:

180 °F

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Hexanes (Slightly)

form 

liquid

color 

Pale green to khaki-brown

Specific Gravity

0.889

Water Solubility 

Difficult to mix with water.

InChI

InChI=1S/C12H14/c1-5-10-6-8-11(9-7-10)12(2,3)4/h1,6-9H,2-4H3

InChIKey

ZSYQVVKVKBVHIL-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

772-38-3(CAS DataBase Reference)

Safety

Hazard Codes 

N,Xi

Risk Statements 

50/53

Safety Statements 

36/37-60-61

RIDADR 

UN 3082 9/PG 3

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

9

HS Code 

29029090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

4-(TERT-BUTYL)PHENYLACETYLENE Chemical Properties,Usage,Production

Uses

4-(tert-Butyl)phenylacetylene is a useful research chemical.

Chemical Properties

Clear pale yellowish-brown liquid

Uses

4-tert-Butylphenylacetylene is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Uses

4-tert-Butylphenylacetylene can be used in the synthesis of the following:

• 1,6-bis(4-tert-butylphenyl)hexa-1,5-diyne-3,4-dione
• 4,4′,5,5′-tetra(4-tert-butylphenylethynyl)dibenzo-24-crown-8-ether via Sonogashira coupling reaction with 4,4′,5,5′-tetraiododibenzo-24-crown-8-ether
• 1-(4-tert-butylphenyl)-2-(4-tert-butyldimethylsiloxyphenyl)acetylene via palladium catalyzed coupling with 4-(tert-butyldimethylsiloxy)iodobenzene

General Description

4-tert-Butylphenylacetylene can be synthesized from 4-tert-butylstyrene.

Synthesis

General procedure for the synthesis of 4-tert-butylphenylacetylene from the compound (CAS:135883-30-6): the raw material (5.0 g, 21.7 mmol) was dissolved in a solvent mixture of 50 mL of methanol and 50 mL of dichloromethane, and finely powdered potassium carbonate (6.0 g, 43.5 mmol) was added. The suspension was stirred at room temperature for 3 hours. After completion of the reaction, the mixture was filtered through a bed of diatomaceous earth, water was added to the filtrate and extracted with ether. The ether layers were combined and washed twice with water (50 mL each), then the extract was dried with anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure to give a colorless liquid product. The structure of the product was confirmed by 1H-NMR spectroscopy (CDCl3, 300 MHz): δ 1.33 (s, 9H), 3.04 (s, 1H), 7.35 (d, 2H, J = 8.3 Hz), 7.45 (d, 2H, J = 9.0 Hz). Mass spectrometry (EI) showed a molecular ion peak m/z 158.0 [M]+. The separation yield was 96% (3.3 g).

References

[1] Canadian Journal of Chemistry, 2001, vol. 79, # 5-6, p. 878 - 887
[2] Tetrahedron Letters, 2011, vol. 52, # 51, p. 6942 - 6947
[3] Organic Letters, 2014, vol. 16, # 3, p. 948 - 951
[4] Tetrahedron, 1997, vol. 53, # 45, p. 15515 - 15534
[5] Russian Journal of Organic Chemistry, 2000, vol. 36, # 8, p. 1157 - 1162