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benzvalene
Sign in to saveBenzvalene is an organic compound and one of several isomers of benzene. It was first synthesized in 1967 by K. E. Wilzbach et al. via photolysis of benzene and the synthesis was later improved by Thomas J. Katz et al.
Chemical data
- Formula
- C6H6
- Molecular weight
- 78.11 g/mol
- IUPAC name
- tricyclo[3.1.0.02,6]hex-3-ene
- SMILES
- C1=CC2C3C1C23
- InChIKey
- VMQPMGHYRISRHO-UHFFFAOYSA-N
- XLogP
- 1
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Has part
- hydrogen
- Mass
- 78.04695
Show 3 more facts
- chemical formula
- C₆H₆
- canonical SMILES
- C1=CC2C3C1C23
- Commons category
- Benzvalene
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Polybenzvalene
- References
- External links
Benzvalene is an organic compound and one of several isomers of benzene. It was first synthesized in 1967 by K. E. Wilzbach et al. via photolysis of benzene and the synthesis was later improved by Thomas J. Katz et al.
The 1971 synthesis consisted of treating cyclopentadiene with methyllithium in dimethyl ether and then with dichloromethane and methyllithium in dimethyl ether at −45 °C. It can also be formed in low yield (along with fulvene and Dewar benzene) by irradiation of benzene at 237 to 254 nm. The hydrocarbon in solution was described as having an extremely foul odor. Due to the high steric strain present in benzvalene, the pure compound (~71 kcal/mol higher in energy than benzene) easily detonates, for example by scratching.
Excerpted from Wikipedia’s “benzvalene” article, available under the CC BY-SA 4.0 licence.