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.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. 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. Enantioselective routes to chiral indanes and indenes are also available. Routes to the hydroindanes are also relevant.
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.
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.
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. 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]. Nitration of indane gives 4-nitroindane. Reduction of the nitro group then gives 4-aminoindane.Neelu Kaila, et al. WO2005047258 (2005 to Wyeth LLC). This compound finds use in the synthesis of an agent that is called Indanazoline [40507-78-6].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.DE2136325 idem Alex Berg, Hans-Joachim May, (1975 to Nordmark Werke Gmbh). Another compound that is made from indane proper is called Sulofenur (LY181984) [110311-27-8].Gerald A. Poore, (1992 to Eli Lilly And Company). 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.
See also Indene 1,3-Indanedione, a popular starting compound
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