Indane

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Indane
Skeletal formula
Ball-and-stick model of the indane molecule
Names
Preferred IUPAC name
2,3-Dihydro-1H-indene
Other names
Indan
Benzocyclopentane
Hydrindene[1]
2,3-Dihydroindene[1]
Identifiers
3D model (JSmol)
1904376
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.105
67817
Properties
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).
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Infobox references

Indane or indan is an organic compound with the formula C6H4(CH2)3. 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.[2]

Reactions[edit]

Indane can also be converted in a catalytic reactor to other aromatics such as xylene.

Indane is used in the synthesis of sulofenur.[3]

Derivatives[edit]

Derivatives include compounds such as 1-methyl-indane and 2-methyl-indane (where one methyl group is attached to the five carbon ring), 4-methyl-indane and 5-methyl-indane (where one methyl group is attached to the benzene ring), various dimethyl-indanes. 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[edit]

References[edit]

  1. ^ a b Hawley, Gessner G. (1977). The Condensed Chemical Dictionary. Van Nostrand Reinhold Company. p. 464. ISBN 0-442-23240-3.
  2. ^ 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
  3. ^ Howbert, J. Jeffry; Grossman, C. Sue; Crowell, Thomas A.; Rieder, Brent J.; Harper, Richard W.; Kramer, Kenneth E.; Tao, Eddie V.; Aikins, James; Poore, Gerald A. (1990). "Novel agents effective against solid tumors: the diarylsulfonylureas. Synthesis, activities, and analysis of quantitative structure-activity relationships". Journal of Medicinal Chemistry. 33 (9): 2393–2407. doi:10.1021/jm00171a013. ISSN 0022-2623.
  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. PMID 1967651.