Indane

Indane

Names
Preferred IUPAC name 2,3-Dihydro-1H-indene
Other names Indane Benzocyclopentane Hydrindene[1] 2,3-Dihydroindene[1]
Identifiers
CAS Number	496-11-7
3D model (Jmol)	Interactive image
Beilstein Reference	1904376
ChEBI	CHEBI:37911
ChEMBL	ChEMBL370687
ChemSpider	9903
ECHA InfoCard	100.007.105
Gmelin Reference	67817
PubChem	10326
InChI InChI=1S/C9H10/c1-2-5-9-7-3-6-8(9)4-1/h1-2,4-5H,3,6-7H2 Key: PQNFLJBBNBOBRQ-UHFFFAOYSA-N 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	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

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.

See also

• Indene

References

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