Indane

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Indane
Skeletal formula Indane structure.svg
Skeletal formula
Indane 3D ball.png
Names
Preferred IUPAC name
2,3-Dihydro-1H-indene [1]
Other names
Indan
Benzocyclopentane
Hydrindene [2]
2,3-Dihydroindene [2]
Identifiers
3D model (JSmol)
1904376
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.105 OOjs UI icon edit-ltr-progressive.svg
67817
PubChem CID
UNII
  • InChI=1S/C9H10/c1-2-5-9-7-3-6-8(9)4-1/h1-2,4-5H,3,6-7H2 Yes check.svgY
    Key: PQNFLJBBNBOBRQ-UHFFFAOYSA-N Yes check.svgY
  • 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
Appearancecolorless 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).
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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.

Contents

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 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

  1. ↑ 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.
  2. 1 2 Hawley, Gessner G. (1977). The Condensed Chemical Dictionary. Van Nostrand Reinhold Company. p. 464. ISBN   0-442-23240-3.
  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
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