Indane

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Indane
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Names
Preferred IUPAC name
2,3-Dihydro-1H-indene[2]
Other names
Indan
Benzocyclopentane
Hydrindene[1]
2,3-Dihydroindene[1]
Identifiers
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3D model (JSmol)
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1904376
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67817
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  • 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).

Template:Chembox Footer/trackingTemplate:Short description

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

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 to 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

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

References

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  1. ^ a b Page Module:Citation/CS1/styles.css has no content.Hawley, Gessner G. (1977). The Condensed Chemical Dictionary. Van Nostrand Reinhold Company. p. 464. ISBN 0-442-23240-3.
  2. ^ Page Module:Citation/CS1/styles.css has no content.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. Script error: No such module "CS1 identifiers".
  4. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content."(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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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 3882229 (1975 to Nordmark Werke Gmbh).
  14. ^ Page Module:Citation/CS1/styles.css has no content.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 5116874 (1992 to Eli Lilly And Company).
  16. ^ Page Module:Citation/CS1/styles.css has no content.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

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