Azulene

Azulene is an aromatic organic compound and an isomer of naphthalene. Naphthalene is colourless, whereas azulene is dark blue. The compound is named after its colour, as "azul" is Spanish for blue. Two terpenoids, vetivazulene (4,8-dimethyl-2-isopropylazulene) and guaiazulene (1,4-dimethyl-7-isopropylazulene), that feature the azulene skeleton are found in nature as constituents of pigments in mushrooms, guaiac wood oil, and some marine invertebrates.

Azulene
Names
Preferred IUPAC name
Azulene
Systematic IUPAC name
Bicyclo[5.3.0]decapentaene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.449
KEGG
UNII
  • InChI=1S/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H Y
    Key: CUFNKYGDVFVPHO-UHFFFAOYSA-N Y
  • InChI=1/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H
    Key: CUFNKYGDVFVPHO-UHFFFAOYAT
  • c1cccc2cccc2c1
Properties
C10H8
Molar mass 128.174 g·mol−1
Melting point 99 to 100 °C (210 to 212 °F; 372 to 373 K)
Boiling point 242 °C (468 °F; 515 K)
-98.5·10−6 cm3/mol

g/L

Thermochemistry
−1266.5 kcal/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Azulene has a long history, dating back to the 15th century as the azure-blue chromophore obtained by steam distillation of German chamomile. The chromophore was discovered in yarrow and wormwood and named in 1863 by Septimus Piesse. Its structure was first reported by Lavoslav Ružička, followed by its organic synthesis in 1937 by Placidus Plattner.

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