Phenylacetylene

From Wikipedia, the free encyclopedia

Phenylacetylene
IUPAC name	Ethynylbenzene
Identifiers
CAS number	[536-74-3]
SMILES	C#Cc1ccccc1
Properties
Molecular formula	C8H6
Molar mass	102.133 g/mol
Density	0.93 g/cm³
Melting point	–45 °C
Boiling point	142-144 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Phenylacetylene is an alkyne hydrocarbon containing a phenyl group. It exists as a colorless, viscous liquid. In research, it is sometimes used as an analog for acetylene; being a liquid, it is easier to handle than acetylene gas.

Contents 1 Preparation 2 Reactions 3 See also 4 References

[edit] Preparation

In the laboratory, phenylacetylene can be prepared by elimination of hydrogen bromide from styrene dibromide using sodium amide in ammonia.^[1] It can also be prepared by the elimination of hydrogen bromide from bromostyrene using molten potassium hydroxide.^[2]

[edit] Reactions

• Phenylacetylene can be reduced (hydrogenated) by hydrogen over Lindlar catalyst to give styrene.

• It undergoes a metal catalyzed trimerization to give 1,2,4- (97%) and 1,3,5-triphenylbenzene.

.

• It undergoes gold-catalyzed hydrolysis to give acetophenone.

[edit] See also

• Alkyne
• Alkyne trimerisation

[edit] References

The references in this article would be clearer with a different or consistent style of citation, footnoting, or external linking.