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acenaphthene
Sign in to saveAlso known as peri-ethylenenaphthalene
Acenaphthene is a polycyclic aromatic hydrocarbon (PAH) consisting of naphthalene with an ethylene bridge connecting positions 1 and 8. It is a colourless solid. Coal tar consists of about 0.3% of this compound.
In the Vinony graph
Within Vinony's link graph, acenaphthene is referenced by 82 other articles, and connects out to benzo[b]fluoranthene, International Standard Book Number and ethanol.
It is catalogued under topics including Acenaphthylenes, Chembox image size set and Chemical articles with multiple compound IDs.
Its subject is documented across 27 Wikipedia language editions.
Chemical data
- Formula
- C12H10
- Molecular weight
- 154.21 g/mol
- IUPAC name
- 1,2-dihydroacenaphthylene
- SMILES
- C1CC2=CC=CC3=C2C1=CC=C3
- InChIKey
- CWRYPZZKDGJXCA-UHFFFAOYSA-N
- XLogP
- 3.9
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Research
1,164 papers- Study on the mechanism of liver toxicity induced by acenaphthene in zebrafish.Ecotoxicology and environmental safety · 2023
- Oral gepotidacin versus nitrofurantoin in patients with uncomplicated urinary tract infection (EAGLE-2 and EAGLE-3): two randomised, controlled, double-blind, double-dummy, phase 3, non-inferiority trials.Lancet (London, England) · 2024
- Oral gepotidacin for the treatment of uncomplicated urogenital gonorrhoea (EAGLE-1): a phase 3 randomised, open-label, non-inferiority, multicentre study.Lancet (London, England) · 2025
- Gepotidacin: a novel, oral, 'first-in-class' triazaacenaphthylene antibiotic for the treatment of uncomplicated urinary tract infections and urogenital gonorrhoea.The Journal of antimicrobial chemotherapy · 2023
- Colorimetric Detection of Acenaphthene and Naphthalene Using Functionalized Gold Nanoparticles.International journal of molecular sciences · 2023
via PubMed
Wikidata facts
- Mass
- 154.078
Show 7 more facts
- Commons category
- Acenaphthene
- chemical formula
- C₁₂H₁₀
- electric dipole moment
- 0.85
- ionization energy
- 7.68
- boiling point
- 279
- melting point
- 94
- canonical SMILES
- C1CC2=CC=CC3=C2C1=CC=C3
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Production and reactions
- Uses
- References
Acenaphthene is a polycyclic aromatic hydrocarbon (PAH) consisting of naphthalene with an ethylene bridge connecting positions 1 and 8. It is a colourless solid. Coal tar consists of about 0.3% of this compound.
==Production and reactions== Acenaphthene was prepared for the first time in 1866 by Marcellin Berthelot by reacting hot naphthalene vapours with acetylene, and a year later he reproduced a similar reaction with ethylene as well as discovered acenaphthene in coal tar. Later Berthelot and Bardy synthesized the compound by cyclization of α-ethylnaphthalene. Industrially, it is still obtained from coal tar together with its derivative acenaphthylene (and many other compounds).
Excerpted from Wikipedia’s “acenaphthene” article, available under the CC BY-SA 4.0 licence.