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词条 Phenylacetylene
释义

  1. Preparation

  2. Reactions

  3. See also

  4. References

{{chembox
| Watchedfields = changed
| verifiedrevid = 464200987
| Name = Phenylacetylene
| ImageFile = Phenylacetylene.svg
| ImageName = Phenylacetylene
| ImageFile1 = Phenylacetylene-3D-balls.png
| IUPACName = Ethynylbenzene
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10364
| PubChem = 10821
| InChI = 1/C8H6/c1-2-8-6-4-3-5-7-8/h1,3-7H
| InChIKey = UEXCJVNBTNXOEH-UHFFFAOYAC
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 234833
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H6/c1-2-8-6-4-3-5-7-8/h1,3-7H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UEXCJVNBTNXOEH-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 536-74-3
| SMILES = C#Cc1ccccc1
|Section2={{Chembox Properties
| Formula = C8H6
| MolarMass = 102.133 g/mol
| Density = 0.93 g/cm3
| MeltingPtC = -45
| BoilingPtC = 142 to 144
| BoilingPt_notes =
| pKa = 28.7 (DMSO)[1],
23.2 (aq, extrapolated)[2]
| MagSus = -72.01·10−6 cm3/mol
}}

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.

Preparation

In the laboratory, phenylacetylene can be prepared by elimination of hydrogen bromide from styrene dibromide using sodium amide in ammonia:[3]

It can also be prepared by the elimination of hydrogen bromide from bromostyrene using molten potassium hydroxide.[4]

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:[5]

  • Choosing a rhodium catalyst leads to the cyclotrimerization producing both the 1,2,4- and 1,3,5- isomers along with substantial quantities of acyclic enyne dimer products:[6]

  • It undergoes a hydration reaction, catalyzed by gold(III) or mercury(II), to give acetophenone.

See also

  • Alkyne
  • Alkyne trimerisation

References

1. ^Bordwell, F.G. Acc. Chem. Res. 1988, 21, 456-463.
2. ^Streitwieser, A.,Jr.; Ruben, D.M.E; J. Am. Chem. Soc. 1971., 93, 1794-1795.
3. ^{{OrgSynth | prep = cv4p0763 | collvol = 4 | collvolpages = 763 | year = 1963 | title = Phenylacetylene | author = Kenneth N. Campbell and Barbara K. Campbell}}
4. ^{{OrgSynth | prep = cv1p0438 | title = Phenylacetylene | author = John C. Hessler | year = 1941 | collvol = 1 | collvolpages = 438}}
5. ^{{cite journal | title = A simple cobalt catalyst system for the efficient and regioselective cyclotrimerisation of alkynes |author1=Gerhard Hilt |author2=Thomas Vogler |author3=Wilfried Hess |author4=Fabrizio Galbiati | journal = Chemical Communications | year = 2005 | volume = 2005 | issue = 11 | pages = 1474–1475 | doi = 10.1039/b417832g | pmid = 15756340}}
6. ^{{cite journal|title = Oligomerization and Polymerization of Alkynes Catalyzed by Rhodium(I) Pyrazolate Complexes|author1-last = Ardizzoia|author1-first = G. A.|author2-last = Brenna|author2-first = S.|author3-last = Cenini|author3-first = S.|author4-last = LaMonica|author4-first = G.|author5-last = Masciocchi|author5-first = N.|author6-last = Maspero|author6-first= A.|journal = Chemical|year = 2003|volume = 204–205|pages = 333–340|doi = 10.1016/S1381-1169(03)00315-7}}

2 : Alkynes|Phenyl compounds
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