Structure via PubChem · Public domain (PubChem)
azulene
Sign in to saveAlso known as Azulen, cyclopentacycloheptene, bicyclo[5.3.0]decapentaene
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.
Chemical data
- Formula
- C10H8
- Molecular weight
- 128.17 g/mol
- IUPAC name
- azulene
- SMILES
- C1=CC=C2C=CC=C2C=C1
- InChIKey
- CUFNKYGDVFVPHO-UHFFFAOYSA-N
- XLogP
- 3.2
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Research
1,316 papers- Azulene-A Bright Core for Sensing and Imaging.Molecules (Basel, Switzerland) · 2021
- Azulene and Its Derivatives as Potential Compounds in the Therapy of Dermatological and Anticancer Diseases: New Perspectives against the Backdrop of Current Research.Molecules (Basel, Switzerland) · 2024
- Azulene as a biphenyl mimetic in orexin/hypocretin receptor agonists.Bioorganic & medicinal chemistry · 2023
- Synthesis of Azulene Derivatives from 2H-Cyclohepta[b]furan-2-ones as Starting Materials: Their Reactivity and Properties.International journal of molecular sciences · 2021
- Azulene-Containing Squaraines for Photoacoustic Imaging and Photothermal Therapy.ACS applied materials & interfaces · 2022
via PubMed
Wikidata facts
- Mass
- 128.063
- Image
- Sublsublimated azulene.jpg
Show 6 more facts
- canonical SMILES
- C1=CC=C2C=CC=C2C=C1
- chemical formula
- C₁₀H₈
- Commons category
- Azulene
- melting point
- 99
- electric dipole moment
- 0.80
- ionization energy
- 7.41
Sources (3)
via Wikidata · CC0
~4 min read
Article
6 sectionsContents
- Structure and bonding
- Organic synthesis
- Organometallic complexes
- Derivatives
- References
- External links
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 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.