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Phenylacetylene information


Phenylacetylene
Phenylacetylene
Names
Preferred IUPAC name
Ethynylbenzene
Other names
Phenylacetylene
Identifiers
CAS Number
  • 536-74-3 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL234833 checkY
ChemSpider
  • 10364 checkY
ECHA InfoCard 100.007.861 Edit this at Wikidata
PubChem CID
  • 10821
UNII
  • 239WSR2IBO checkY
CompTox Dashboard (EPA)
  • DTXSID1060211 Edit this at Wikidata
InChI
  • InChI=1S/C8H6/c1-2-8-6-4-3-5-7-8/h1,3-7H checkY
    Key: UEXCJVNBTNXOEH-UHFFFAOYSA-N checkY
  • InChI=1/C8H6/c1-2-8-6-4-3-5-7-8/h1,3-7H
    Key: UEXCJVNBTNXOEH-UHFFFAOYAC
SMILES
  • C#Cc1ccccc1
Properties
Chemical formula
C8H6
Molar mass 102.133 g/mol
Density 0.93 g/cm3
Melting point −45 °C (−49 °F; 228 K)
Boiling point 142 to 144 °C (288 to 291 °F; 415 to 417 K)
Acidity (pKa) 28.7 (DMSO),[1]
23.2 (aq, extrapolated)[2]
Magnetic susceptibility (χ)
-72.01·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox 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.

  1. ^ Bordwell, F.G. (1988). "Equilibrium acidities in dimethyl sulfoxide solution". Acc. Chem. Res. 21: 456–463. doi:10.1021/ar00156a004.
  2. ^ Streitwieser, A. Jr.; Ruben, D.M.E (1971). "Acidity of hydrocarbons. XXXV. Equilibrium acidities of phenylacetylene and tert-butylacetylene in cyclohexylamine". J. Am. Chem. Soc. 93: 1794–1795. doi:10.1021/ja00736a045.

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Phenylacetylene

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Phenylacetylene is an alkyne hydrocarbon containing a phenyl group. It exists as a colorless, viscous liquid. In research, it is sometimes used as an...

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Alkyne

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which are first halogenated and then dehydrohalogenated. For example, phenylacetylene can be generated from styrene by bromination followed by treatment...

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Diphenylacetylene

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salt of phenylacetylene in the Castro-Stephens coupling. The related Sonogashira coupling involves the coupling of iodobenzene and phenylacetylene. Diphenylacetylene...

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Lindlar catalyst

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only the triple bond is reduced. An example being the reduction of phenylacetylene to styrene. Alkyne hydrogenation is stereospecific, occurring via syn...

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Sandmeyer reaction

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Swiss chemist Traugott Sandmeyer, when he attempted to synthesize phenylacetylene from benzenediazonium chloride and copper(I) acetylide. Instead, the...

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Benzene

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PAHs Alkylbenzenes Toluene Vinylbenzenes Styrene Divinylbenzene 4-Vinyltoluene Other Benzene Cyclopropenylidene Phenylacetylene trans-Propenylbenzene...

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Sonogashira coupling

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reaction. Acetylene is activated in the second, PdII mediated cycle. Phenylacetylene was proven to form Pd monoacetylide complex D as well as Pd bisacetylide...

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Sodium amide

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dibromoalkane to give a carbon–carbon triple bond, as in a preparation of phenylacetylene. Usually two equivalents of sodium amide yields the desired alkyne...

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Hydrogenation

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alkenes. The Lindlar catalyst has been applied to the conversion of phenylacetylene to styrene. Illustrative hydrogenations Selective hydrogenation of...

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Trimethylsilylacetylene

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trimethylsilyl group can then be cleaved off with TBAF or DBU to form phenylacetylene derivatives. Trimethylsilylacetylene is also used to synthesize diphenylacetylene...

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Diphenylbutadiyne

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(C6H5C2)2. It is a common diyne. It is the product of the coupling of phenylacetylene, often with copper reagents, but a variety of methods have been developed...

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Hydrocarbon

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C8H6

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exact mass: 102.0470 u) may refer to: Benzocyclobutadiene Pentalene Phenylacetylene Calicene, or triapentafulvalene Cubene This set index page lists chemical...

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Styrene

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Xylene

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Toluene

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Isobutylene

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Aromatic compound

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Naphthalene

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Cycloalkane

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Diene

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Alkane

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Phenyl azide

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substituents. In a classic example of click chemistry, phenyl azide and phenylacetylene react to give diphenyl triazole. Phenyl azide reacts with triphenylphosphine...

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Organosilicon chemistry

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"Effect of the synthetic method of Pt/MgO in the hydrosilylation of phenylacetylene" (PDF). Arkivoc. 126: 136. Linderman, Russell J.; Stiasni, Nikola;...

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Phenanthrene

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Polycyclic aromatic hydrocarbon

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