Indane

This article is about the hydrocarbon. For the binary compound of hydrogen and indium, see Indium trihydride. For other uses, see Indane (disambiguation).

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.

Indane

Skeletal formula
Names
Preferred IUPAC name 2,3-Dihydro-1H-indene[1]
Other names Indan Benzocyclopentane Hydrindene[2] 2,3-Dihydroindene[2]
Identifiers
CAS Number	496-11-7 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1904376
ChEBI	CHEBI:37911 Y
ChEMBL	ChEMBL370687 Y
ChemSpider	9903 Y
ECHA InfoCard	100.007.105
Gmelin Reference	67817
PubChem CID	10326
UNII	H9SCX043IG Y
CompTox Dashboard (EPA)	DTXSID4052132
InChI InChI=1S/C9H10/c1-2-5-9-7-3-6-8(9)4-1/h1-2,4-5H,3,6-7H2 Y Key: PQNFLJBBNBOBRQ-UHFFFAOYSA-N Y InChI=1/C9H10/c1-2-5-9-7-3-6-8(9)4-1/h1-2,4-5H,3,6-7H2 Key: PQNFLJBBNBOBRQ-UHFFFAOYAW
SMILES c1ccc2c(c1)CCC2
Properties
Chemical formula	C9H10
Molar mass	118.176 g/mol
Appearance	colorless 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). Y verify (what is YN ?) Infobox references

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.

• 
  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]

See also

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