Indane

Indane or indan is an organic compound with the formula C 9 H 10 . 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.

Indane or indan is an organic compound with the formula C 9 H 10 . 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. 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. File:Indinavir structure.svg|Indinavir for treatment of HIV/AIDS File:Rasagiline structure.svg|Rasagiline for treatment of Parkinson's disease File:Ramelteon skeletal formula.svg|Ramelteon for treatment of insomnia File:5-APDI.svg|5-APDI (c.f. 5-MAPDI) File:MDAI structure.svg|5,6-methylenedioxy-2-aminoindane, a recreational drug related to MDMA 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. This compound finds use in the synthesis of an agent that is called Indanazoline [40507-78-6]. Another compound that is made from indane proper is called Sulofenur (LY181984) [110311-27-8]. 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 ==References==

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