Indene

Indene is an aromatic, polycyclic hydrocarbon with chemical formula C9H8. It is composed of a benzene ring fused with a cyclopentene ring. This flammable liquid is colorless although samples often are pale yellow. The principal industrial use of indene is in the production of indene/coumarone thermoplastic resins. Substituted indenes and their closely related indane derivatives are important structural motifs found in many natural products and biologically active molecules, such as sulindac.

Indene
Names
Preferred IUPAC name
1H-Indene
Other names
Benzocyclopentadiene
Indonaphthene
Bicyclo[4.3.0]nona-1,3,5,7-tetraene
Identifiers
3D model (JSmol)
635873
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.002.176
EC Number
  • 202-393-6
27265
KEGG
PubChem CID
UNII
  • InChI=1S/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2 Y
    Key: YBYIRNPNPLQARY-UHFFFAOYSA-N Y
  • InChI=1/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2
    Key: YBYIRNPNPLQARY-UHFFFAOYAJ
SMILES
  • c1ccc2c(c1)CC=C2
Properties
C9H8
Molar mass 116.16
Appearance Colorless liquid
Density 0.997 g/mL
Melting point −1.8 °C (28.8 °F; 271.3 K)
Boiling point 181.6 °C (358.9 °F; 454.8 K)
Insoluble
Acidity (pKa) 20.1 (in DMSO)
Magnetic susceptibility (χ)
 −80.89×10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Flammable
Flash point 78.3 °C (172.9 °F; 351.4 K)
NIOSH (US health exposure limits):
PEL (Permissible)
 none
REL (Recommended)
 TWA 10 ppm (45 mg/m3)
IDLH (Immediate danger)
 N.D.
Related compounds
Related compounds
 Benzofuran, Benzothiophene, Indole
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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