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
Indane
Benzocyclopentane
Hydrindene[1]
2,3-Dihydroindene[1]
Identifiers
3D model (JSmol)
1904376
ChEBI
ChemSpider
ECHA InfoCard 100.007.105
67817
Properties
C9H10
Molar mass 118.176 g/mol
Appearance Clear colorless liquid
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 a hydrocarbon petrochemical compound, with formula C9H10.

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, and various pharmaceutical derivatives. 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.

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

Another derivative is 1,3-indandione.

Dr. David E. Nichols developed a family of indane derivatives that are empathogen-entactogens. They are very close derivatives of other empathogen-entactogens such as MDMA and MDA. However, they are not neurotoxic at therapeutic doses because the alpha-methyl group is bound and therefore cannot form a free radical. Examples include MDAI, MDMAI, and MDAT.[2] Nichols also created an indane isomer of amphetamine, 2-aminoindane, and an iodized derivative 5-IAI.

Indane is also known to be used in the synthesis of sulofenur.[3]

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. ^ Nichols DE, Brewster WK, Johnson MP, Oberlender R, Riggs RM. Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA). Journal of Medicinal Chemistry. 1990 Feb;33(2):703-10. PMID 1967651
  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. 

3. https://pubchem.ncbi.nlm.nih.gov/compound/10326#section=Top