Chemistry:Indane

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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.[1] 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.[2] Enantioselective routes to chiral indanes and indenes are also available.[3] Routes to the hydroindanes are also relevant.[4]

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.[5]

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.[6]

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.[7] 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].[8] Nitration of indane gives 4-nitroindane. Reduction of the nitro group then gives 4-aminoindane.[9] This compound finds use in the synthesis of an agent that is called Indanazoline [40507-78-6].[10][11] Another compound that is made from indane proper is called Sulofenur (LY181984) [110311-27-8].[12][13] 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.[14]

See also

  • Indene
  • 1,3-Indanedione, a popular starting compound

References

  1. ↑ 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
  2. ↑ Gabriele, Bartolo; Mancuso, Raffaella; Veltri, Lucia (2016). "Recent Advances in the Synthesis of Indanes and Indenes". Chemistry – A European Journal 22 (15): 5056–5094. doi:10.1002/chem.201503933. PMID 26788795. Bibcode: 2016ChEuJ..22.5056G. 
  3. ↑ 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. 
  4. ↑ 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. 
  5. ↑ Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef et al. (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a19_313. ISBN 978-3-527-30385-4. 
  6. ↑ "(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. 
  7. ↑ 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. 
  8. ↑ 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. https://pubs.acs.org/doi/abs/10.1021/ja01234a036. Retrieved 4 November 2025. 
  9. ↑ Neelu Kaila, et al. WO2005047258 (2005 to Wyeth LLC).
  10. ↑ 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.
  11. ↑ DE2136325 idem Alex Berg, Hans-Joachim May, U.S. Patent 3,882,229 (1975 to Nordmark Werke Gmbh).
  12. ↑ Howbert, J. J.; Grossman, C. S.; Crowell, T. A.; Rieder, B. J.; Harper, R. W.; Kramer, K. E.; Tao, E. V.; Aikins, J. et al. (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. https://pubs.acs.org/doi/abs/10.1021/jm00171a013. 
  13. ↑ Gerald A. Poore, U.S. Patent 5,116,874 (1992 to Eli Lilly And Company).
  14. ↑ 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 82 (10): 2553–2556, doi:10.1021/ja01495a039 



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