tolan
Sign in to saveAlso known as diphenylacetylene, tolane, diphenylethyne, 1,2-diphenylacetylene
Diphenylacetylene is the chemical compound C6H5C≡CC6H5. The molecule consists of two phenyl groups attached to a C2 unit. A colorless solid, it is used as a building block in organic synthesis and as a ligand in organometallic chemistry.
Wikidata facts
- Subclass of
- chemical compound
- Has part
- hydrogen
- Mass
- 178.078
Show 6 more facts
- chemical formula
- C₁₄H₁₀
- canonical SMILES
- C1=CC=C(C=C1)C#CC2=CC=CC=C2
- Commons category
- Diphenylacetylene
- melting point
- 62.5
- ionization energy
- 7.90
- boiling point
- 300
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Encyclopedic overview
3 sectionsContents
- Preparation and structure
- Derivatives
- References
Diphenylacetylene is the chemical compound C6H5C≡CC6H5. The molecule consists of two phenyl groups attached to a C2 unit. A colorless solid, it is used as a building block in organic synthesis and as a ligand in organometallic chemistry.
==Preparation and structure== In one preparation for this compound, benzil is condensed with hydrazine to give the bis(hydrazone), which is oxidized with mercury(II) oxide. Alternatively stilbene is brominated, and the resulting dibromodiphenylethane is subjected to dehydrohalogenation. Yet another method involves the coupling of iodobenzene and the copper salt of phenylacetylene in the Castro-Stephens coupling. The related Sonogashira coupling involves the coupling of iodobenzene and phenylacetylene.
Excerpted from Wikipedia’s “tolan” article, available under the CC BY-SA 4.0 licence.