Indane

This article is about the hydrocarbon. For the binary compound of hydrogen and indium, see Indium trihydride. For other uses, see Indane (disambiguation).

Indane or indan is an organic compound with the formula C₉H₁₀. It is a colorless liquid hydrocarbon. It is a petrochemical, a bicyclic compound. It occurs at the level of about 0.1% in coal tar. It is usually produced by hydrogenation of indene.^[3]

Indane

Names
Preferred IUPAC name 2,3-Dihydro-1H-indene[1]
Other names Indan Benzocyclopentane Hydrindene[2] 2,3-Dihydroindene[2]
Identifiers
CAS Number	496-11-7 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1904376
ChEBI	CHEBI:37911 Y
ChEMBL	ChEMBL370687 Y
ChemSpider	9903 Y
ECHA InfoCard	100.007.105
Gmelin Reference	67817
PubChem CID	10326
UNII	H9SCX043IG Y
CompTox Dashboard (EPA)	DTXSID4052132
InChI InChI=1S/C9H10/c1-2-5-9-7-3-6-8(9)4-1/h1-2,4-5H,3,6-7H2 Y Key: PQNFLJBBNBOBRQ-UHFFFAOYSA-N Y InChI=1/C9H10/c1-2-5-9-7-3-6-8(9)4-1/h1-2,4-5H,3,6-7H2 Key: PQNFLJBBNBOBRQ-UHFFFAOYAW
SMILES c1ccc2c(c1)CCC2
Properties
Chemical formula	C9H10
Molar mass	118.176 g/mol
Appearance	colorless liquid
Density	0.9645 g/cm3
Melting point	−51.4 °C (−60.5 °F; 221.8 K)
Boiling point	176.5 °C (349.7 °F; 449.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Derivatives

Derivatives include compounds such as 1-methylindane and 2-methylindane (where one methyl group is attached to the five carbon ring), 4-methylindane and 5-methylindane (where one methyl group is attached to the benzene ring), and various dimethylindanes. Other derivatives can be obtained indirectly, e.g. the reaction of diethyl phthalate with ethyl acetate, using metallic sodium and ethanol as a catalyst. The reaction yields indanedione ethyl ester, which can react with the sodium ions yielding a salt. This can be reversed by adding an aqueous solution of hydrochloric acid.

A family of indane derivatives are empathogen-entactogens. They are very close derivatives of other empathogen-entactogens such as MDMA and MDA. Examples include MDAI and MDMAI.^[4] Nichols also created an indane isomer of amphetamine, 2-aminoindane, NM-2-AI, and an iodized derivative 5-IAI.

See also

• Indene
• 1,3-indandione

References

1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 602. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
2. Hawley, Gessner G. (1977). The Condensed Chemical Dictionary. Van Nostrand Reinhold Company. p. 464. ISBN 0-442-23240-3.
3. Karl Griesbaum, Arno Behr, Dieter Biedenkapp, Heinz-Werner Voges, Dorothea Garbe, Christian Paetz, Gerd Collin, Dieter Mayer, Hartmut Höke "Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry 2002 Wiley-VCH, Weinheim. doi:10.1002/14356007.a13_227
4. Nichols, D. E; Brewster, W. K; Johnson, M. P; Oberlender, R; Riggs, R. M (1990). "Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA)". Journal of Medicinal Chemistry. 33 (2): 703–10. doi:10.1021/jm00164a037. PMID 1967651.