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Indane

From Wikipedia, the free encyclopedia
This article is about the hydrocarbon. For the binary compound of hydrogen and indium, seeIndium trihydride. For other uses, seeIndane (disambiguation).
Indane
Skeletal formula
Skeletal formula
Ball-and-stick model of the indane molecule
Names
Preferred IUPAC name
2,3-Dihydro-1H-indene[2]
Other names
Indan
Benzocyclopentane
Hydrindene[1]
2,3-Dihydroindene[1]
Identifiers
3D model (JSmol)
1904376
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.007.105Edit this at Wikidata
67817
UNII
  • InChI=1S/C9H10/c1-2-5-9-7-3-6-8(9)4-1/h1-2,4-5H,3,6-7H2 checkY
    Key: PQNFLJBBNBOBRQ-UHFFFAOYSA-N checkY
  • InChI=1/C9H10/c1-2-5-9-7-3-6-8(9)4-1/h1-2,4-5H,3,6-7H2
    Key: PQNFLJBBNBOBRQ-UHFFFAOYAW
  • c1ccc2c(c1)CCC2
Properties
C9H10
Molar mass118.176 g/mol
Appearancecolorless liquid
Density0.9645 g/cm3
Melting point−51.4 °C (−60.5 °F; 221.8 K)
Boiling point176.5 °C (349.7 °F; 449.6 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Indane orindan is anorganic compound with the formula C9H10. It is a colorless liquidhydrocarbon. It is apetrochemical, a bicyclic compound. It occurs at the level of about 0.1% incoal tar. It is usually produced by hydrogenation ofindene.[3]

Derivatives

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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 ofdiethyl phthalate withethyl acetate, using metallicsodium andethanol 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 ofhydrochloric acid.[citation needed]

A family of indane derivatives areempathogen-entactogens. They are very close derivatives of other empathogen-entactogens such asMDMA andMDA. Examples includeMDAI andMDMAI.[4] Nichols also created an indane isomer ofamphetamine,2-aminoindane,NM-2-AI, and an iodized derivative5-IAI.

BK-Imp [100608-69-3]

Indane can be used to prepare 5-propionylindane [63998-49-2].[5]

See also

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References

[edit]
  1. ^abHawley, Gessner G. (1977).The Condensed Chemical Dictionary. Van Nostrand Reinhold Company. p. 464.ISBN 0-442-23240-3.
  2. ^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.
  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.
  5. ^Arnold, R. T., Barnes, R. A. (June 1944)."The Jacobsen Rearrangement. VIII. 1 Cyclic Systems; Mechanism".Journal of the American Chemical Society.66 (6):960–964.doi:10.1021/ja01234a036. Retrieved4 November 2025.
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