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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.
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
Article
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).