Indane

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 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.

• 
  Crixivan for treatment of HIV/AIDS
• 
  Rasagiline fortreatment of Parkinson's disease
• 
  Ramelteon for treatment of insomnia
• 
  5-APDI (c.f. 5-MAPDI)
• 
  5,6-methylenedioxy-2-aminoindane, a recreational drug related to MDMA

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]

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