Indane

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title: "Indane" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["indanes"] topic_path: "general/indanes" source: "https://en.wikipedia.org/wiki/Indane" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::callout[type=note] the hydrocarbon ::

| Watchedfields = changed | verifiedrevid = 443871122 | ImageFile=Indane structure.svg | ImageClass = skin-invert-image | ImageSize=170px | ImageName=Skeletal formula | ImageFile1=Indane 3D ball.png | ImageClass1=bg-transparent | ImageSize1=200px | ImageAlt1=Ball-and-stick model of the indane molecule | PIN = 2,3-Dihydro-1H-indene | OtherNames = Indan Benzocyclopentane

Hydrindene 2,3-Dihydroindene |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 9903 | InChI = 1/C9H10/c1-2-5-9-7-3-6-8(9)4-1/h1-2,4-5H,3,6-7H2 | InChIKey = PQNFLJBBNBOBRQ-UHFFFAOYAW | ChEMBL_Ref = | ChEMBL = 370687 | StdInChI_Ref = | StdInChI = 1S/C9H10/c1-2-5-9-7-3-6-8(9)4-1/h1-2,4-5H,3,6-7H2 | StdInChIKey_Ref = | StdInChIKey = PQNFLJBBNBOBRQ-UHFFFAOYSA-N | CASNo_Ref = | CASNo=496-11-7 | UNII_Ref = | UNII = H9SCX043IG | PubChem=10326 | ChEBI_Ref = | ChEBI = 37911 | SMILES = c1ccc2c(c1)CCC2 | Beilstein = 1904376 | Gmelin = 67817 |Section2={{Chembox Properties | Formula=C9H10 | MolarMass=118.176 g/mol | Appearance=colorless liquid | Density=0.9645 g/cm3 | MeltingPtC=-51.4 | BoilingPtC=176.5 | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt =

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. 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. 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|Crixivan for treatment of HIV/AIDS File:Rasagiline2DCSD.svg|Rasagiline fortreatment of Parkinson's disease Ramelteon, sold under the brand name Rozerem among others, is a melatonin agonist medication which is used in the treatment of insomnia File:Ramelteon skeletal formula.svg|Ramelteon for treatment of insomnia File:Indanylaminopropane.svg|5-APDI (c.f. 5-MAPDI) File:MDAI.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.

References

References

  1. [[International Union of Pure and Applied Chemistry]]. (2014). "Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013". [[Royal Society of Chemistry.
  2. Hawley, Gessner G.. (1977). "The Condensed Chemical Dictionary". Van Nostrand Reinhold Company.
  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. (2016). "Recent Advances in the Synthesis of Indanes and Indenes". Chemistry – A European Journal.
  5. (2016). "Enantioselective syntheses of indanes: From organocatalysis to C–H functionalization". Chemical Society Reviews.
  6. (1999). "Recent Advances in the Synthesis of Indan Systems. A Review". Organic Preparations and Procedures International.
  7. (2000). "Ullmann's Encyclopedia of Industrial Chemistry".
  8. (1997). "(S)-Tetrahydro-1-Methyl-3,3-Diphenyl-1H,3H-Pyrrolo-[1,2-c][1,3,2]Oxazaborole-Borane Complex". Organic Syntheses.
  9. (1990). "Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA)". Journal of Medicinal Chemistry.
  10. (June 1944). "The Jacobsen Rearrangement. VIII. 1 Cyclic Systems; Mechanism". Journal of the American Chemical Society.
  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, {{US patent. 3882229 (1975 to Nordmark Werke Gmbh).
  14. (September 1990). "Novel agents effective against solid tumors: the diarylsulfonylureas. Synthesis, activities, and analysis of quantitative structure-activity relationships". Journal of Medicinal Chemistry.
  15. Gerald A. Poore, {{US patent. 5116874 (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".

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indanes