Wikipedia

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
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 InfoCard 100.007.105 Edit 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 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).
checkY verify (what is checkY☒N ?)

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. Many modified indanes are known.

Production of indane skeleton

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Indane itself is usually produced by hydrogenation of indene.[3] More complex indanes are produced by cyclization of phenylpropionic acid and related compounds under Friedel-Crafts reaction conditions. Such routes afford 1-indanone, which can be reduced indanol or the indane. 2-Bromoaryl derivatives with unsaturated substituents undergo Heck reactions (palladium-catalyzed) involving formal loss of HBr and cyclization to indanes and indenes.[4] Enantioselective routes to chiral indanes and indenes are also available.[5] Routes to the hydroindanes are also relevant.[6]

Derivatives

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Derivatives include 1- and 2-methylindanes (where a methyl group is attached to the five carbon ring) as well as 4- and 5-methylindanes (where a methyl group is attached to the benzene ring). Various dimethylindanes are known. 1,1,3,3-Tetramethylindane is produced commercially.[7]

Many indanes can be prepared by reactions of indane with electrophiles, which attack the 5-position (on the benzene ring). For example, sulfonation gives indane-5-sulfonic acid. Base hydrolysis of which gives 5-indanol.[8]

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.[9] Other derivatives include 2-aminoindane, NM-2-AI and the 5-iodo derivative 5-IAI.

Indane can be used to prepare 5-propionylindane [63998-49-2].[10] Nitration of indane gives 4-nitroindane. Reduction of the nitro group then gives 4-aminoindane.[11] This compound finds use in the synthesis of an agent that is called Indanazoline [40507-78-6].[12][13] Another compound that is made from indane proper is called Sulofenur (LY181984) [110311-27-8].[14][15] Glyhexamide [451-71-8] is another example of such a compound prepared from indane starting material. Glidazamide [3074-35-9] is a further example of sulfonyl urea prepared from indaneGlyhexamide and glidazamide are typical sulfonylurea antidiabetics (hypoglycemics), whereas Sulofenur has anticarcinogenic properties.

Hydrogenation of indane gives the saturated derivative hydrindane.[16]

See also

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References

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  1. ^ a b Hawley, 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. ^ Gabriele, Bartolo; Mancuso, Raffaella; Veltri, Lucia (2016). "Recent Advances in the Synthesis of Indanes and Indenes". Chemistry – A European Journal. 22 (15): 5056–5094. Bibcode:2016ChEuJ..22.5056G. doi:10.1002/chem.201503933. PMID 26788795.
  5. ^ Borie, Cyril; Ackermann, Lutz; Nechab, Malek (2016). "Enantioselective syntheses of indanes: From organocatalysis to C–H functionalization". Chemical Society Reviews. 45 (5): 1368–1386. doi:10.1039/c5cs00622h. PMID 26728953.
  6. ^ Hong, Bor-Cherng; Sarshar, Sepehr (1999). "Recent Advances in the Synthesis of Indan Systems. A Review". Organic Preparations and Procedures International. 31: 1–86. doi:10.1080/00304949909355675.
  7. ^ Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe, Dorothea; Paulus, Wilfried (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a19_313. ISBN 978-3-527-30385-4.
  8. ^ "(S)-Tetrahydro-1-Methyl-3,3-Diphenyl-1H,3H-Pyrrolo-[1,2-c][1,3,2]Oxazaborole-Borane Complex". Organic Syntheses. 74: 50. 1997. doi:10.15227/orgsyn.074.0050.
  9. ^ 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.
  10. ^ 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. Retrieved 4 November 2025.
  11. ^ Neelu Kaila, et al. WO2005047258 (2005 to Wyeth LLC).
  12. ^ May HJ. [Synthesis of N-(2-imidazolin-2-yl)-N-(4-indanyl)amine (indanazoline) (author's transl)]. Arzneimittelforschung. 1980;30(10):1733-7. PMID: 7192113.
  13. ^ DE2136325 idem Alex Berg, Hans-Joachim May, U.S. patent 3,882,229 (1975 to Nordmark Werke Gmbh).
  14. ^ Howbert, J. J., Grossman, C. S., Crowell, T. A., Rieder, B. J., Harper, R. W., Kramer, K. E., Tao, E. V., Aikins, J., Poore, G. A. (September 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.
  15. ^ Gerald A. Poore, U.S. patent 5,116,874 (1992 to Eli Lilly And Company).
  16. ^ Norman L. Allinger, James L. Coke (1960), "The Relative Stabilities of cis and trans Isomers. VII. The Hydrindanes 1,2", Journal of the American Chemical Society, vol. 82, no. 10, pp. 2553–2556, doi:10.1021/ja01495a039