File:Anthracene-numbering.svg · Wikimedia Commons · See Wikimedia Commons
anthracene
Sign in to saveAnthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the production of the red dye alizarin and other dyes, as a scintillator to detect high energy particles, as production of pharmaceutical drugs. Anthracene is colorless but exhibits a blue (400–500 nm peak) fluorescence under ultraviolet radiation.
Chemical data
- Formula
- C14H10
- Molecular weight
- 178.23 g/mol
- IUPAC name
- anthracene
- SMILES
- C1=CC=C2C=C3C=CC=CC3=CC2=C1
- InChIKey
- MWPLVEDNUUSJAV-UHFFFAOYSA-N
- XLogP
- 4.4
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 178.078
- Image
- Anthracene.jpg
Show 8 more facts
- chemical formula
- C₁₄H₁₀
- melting point
- 215.0
- canonical SMILES
- C1=CC=C2C=C3C=CC=CC3=CC2=C1
- Commons category
- Anthracene
- MCN code
- 2902.90.30
- electric dipole moment
- 0
- boiling point
- 339.95
- ionization energy
- 7.45
via Wikidata · CC0
~6 min read
Article
14 sectionsContents
- History and etymology
- Occurrence and production
- Reactions
- Reduction
- Cycloadditions
- With electrophiles
- Uses
- Electronics
- Derivatives
- Toxicology
- See also
- References
- Cited sources
- External links
Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the production of the red dye alizarin and other dyes, as a scintillator to detect high energy particles, as production of pharmaceutical drugs. Anthracene is colorless but exhibits a blue (400–500 nm peak) fluorescence under ultraviolet radiation.
== History and etymology == Crude anthracene (with a melting point of only 180°) was discovered in 1832 by Jean-Baptiste Dumas and Auguste Laurent who crystalized it from a fraction of coal tar later known as "anthracene oil". Since their (inaccurate) measurements showed the proportions of carbon and hydrogen of it to be the same as in naphthalene, Laurent called it paranaphtaline in his 1835 publication of the discovery, which is translated to English as paranaphthalene. Two years later, however, he decided to rename the compound to its modern name derived from because after discovering other polyaromatic hydrocarbons he decided it was only one of isomers of naphthalene. This notion was disproved in 1850s and 1860s.