Indene

Indene

Names
Preferred IUPAC name 1H-Indene
Systematic IUPAC name Bicyclo[4.3.0]nona-1,3,5,7-tetraene
Other names Benzocyclopentadiene Indonaphthene
Identifiers
CAS Number	95-13-6
3D model (Jmol)	Interactive image
Beilstein Reference	635873
ChEBI	CHEBI:41921
ChEMBL	ChEMBL192812
ChemSpider	6949
DrugBank	DB02815
ECHA InfoCard	100.002.176
Gmelin Reference	27265
KEGG	C11565
PubChem	7219
InChI InChI=1S/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2 Key: YBYIRNPNPLQARY-UHFFFAOYSA-N 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
Chemical formula	C9H8
Molar mass	116.16
Appearance	Colorless liquid[1]
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)
Solubility in water	Insoluble
Acidity (pKa)	20.1 (in DMSO)[2]
Hazards
Main hazards	Flammable
Flash point	78.3 °C (172.9 °F; 351.4 K)
US health exposure limits (NIOSH):
PEL (Permissible)	none[1]
REL (Recommended)	TWA 10 ppm (45 mg/m^3)[1]
IDLH (Immediate danger)	N.D.[1]
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

Indene is a flammable polycyclic hydrocarbon with chemical formula C₉H₈. It is composed of a benzene ring fused with a cyclopentene ring. This aromatic liquid is colorless although samples often are pale yellow. The principal industrial use of indene is in the production of indene/coumarone thermoplastic resins.

Isolation

Indene occurs naturally in coal-tar fractions boiling around 175–185 °C. It can be obtained by heating this fraction with sodium to precipitate solid "sodio-indene." This step exploits indene's weak acidity evidenced by its deprotonation by sodium to give the indenyl derivative. The sodio-indene is converted back to indene by steam distillation.^[3]

Reactivity

Indene readily polymerises. Oxidation of indene with acid dichromate yields homophthalic acid (o-carboxylphenylacetic acid). It condenses with ethyl oxalate in the presence of sodium ethoxide to form indene-oxalic ester, and with aldehydes or ketones in the presence of alkali to form benzofulvenes. The latter are highly coloured. An indene is also a precursor to the indenyl anion, a ligand in organometallic chemistry with some notability due to the indenyl effect.

See also

• Indane
• Indole
• Isoindene
• Indenyl effect
• Indenone

References

1. "NIOSH Pocket Guide to Chemical Hazards #0340". National Institute for Occupational Safety and Health (NIOSH).
2. Bordwell FG (1988). "Equilibrium acidities in dimethyl sulfoxide solution". Accounts of Chemical Research. 21 (12): 456–463. doi:10.1021/ar00156a004. Bordwell pKa Table in DMSO
3. Gerd Collin, Rolf Mildenberg, Mechthild Zander, Hartmut Höke, William McKillip, Werner Freitag, Wolfgang Imöhl “Resins, Synthetic” Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2000.

External links

• W. v. Miller, Rohde (1890). "Zur Synthese von Indenderivaten". Berichte der deutschen chemischen Gesellschaft. 23 (2): 1881–1886. doi:10.1002/cber.18900230227.
• W. v. Miller, Rohde (1890). "Zur Synthese von Indenderivaten". Berichte der deutschen chemischen Gesellschaft. 23 (2): 1887–1902. doi:10.1002/cber.18900230228.
• Finar, I. L. (1985). Organic Chemistry. Longman Scientific & Technical. ISBN 0-582-44257-5.