Indene
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| Names | |
|---|---|
| Preferred IUPAC name
1H-Indene[1] | |
| 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
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100.002.176 |
| EC Number |
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| 27265 | |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C9H8 | |
| Molar mass | 116.16 |
| Appearance | Colorless liquid[2] |
| 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)[3] |
| −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)
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none[2] |
REL (Recommended)
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TWA 10 ppm (45 mg/m3)[2] |
IDLH (Immediate danger) |
N.D.[2] |
| 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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Indene is an
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.[4]
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.[5]
Reactivity
Indene readily
organolithium
reagents gives lithium indenyl compounds:
- C9H8 + RLi → LiC9H7 + RH
Indenyl is a ligand in organometallic chemistry, giving rise to many transition metal indenyl complexes.[6]
See also
References
- ISBN 978-0-85404-182-4.
- ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0340". National Institute for Occupational Safety and Health (NIOSH).
- ^ Bordwell FG (1988). "Equilibrium acidities in dimethyl sulfoxide solution". . Bordwell pKa Table in DMSO Archived 2008-10-09 at the Wayback Machine
- .
- ISBN 978-3527306732.
- .
External links
- W. v. Miller, Rohde (1890). "Zur Synthese von Indenderivaten". Berichte der Deutschen Chemischen Gesellschaft. 23 (2): 1881–1886. .
- W. v. Miller, Rohde (1890). "Zur Synthese von Indenderivaten". Berichte der Deutschen Chemischen Gesellschaft. 23 (2): 1887–1902. .
- Finar, I. L. (1985). Organic Chemistry. Longman Scientific & Technical. ISBN 0-582-44257-5.
| Authority control databases: National |
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