Phenylacetylene
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| Phenylacetylene | |
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| Systematic name | Ethynylbenzene |
| Chemical formula | C8H6 |
| Molecular mass | 102.133 g/mol |
| Density | 0.93 g/cm3 |
| Melting point | –45 °C |
| Boiling point | 142-144 °C |
| CAS number | [536-74-3] |
| SMILES | C#Cc1ccccc1 |
| 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.
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[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
- Phenyacetylene 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.
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- It undergoes hydrolysis to give acetophenone.
[edit] See also
[edit] References
- ^ Organic Synthesis, http://www.orgsyn.org/orgsyn/prep.asp?prep=cv4p0763
- ^ Organic Synthesis, http://www.orgsyn.org/orgsyn/prep.asp?prep=cv1p0438
