# Indane > Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Indane > Markdown URL: https://mediated.wiki/source/Indane.md > Source: https://en.wikipedia.org/wiki/Indane > Source revision: 1340890901 > License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/) {{About|the hydrocarbon|the binary compound of hydrogen and indium|Indium trihydride|other uses}} {{chembox | 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-1''H''-indene{{cite book |author=[International Union of Pure and Applied Chemistry](/source/International_Union_of_Pure_and_Applied_Chemistry) |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=[The Royal Society of Chemistry](/source/Royal_Society_of_Chemistry) |page=602 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}} | OtherNames = Indan
Benzocyclopentane
Hydrindene{{cite book|author=Hawley, Gessner G.|title=The Condensed Chemical Dictionary|publisher=Van Nostrand Reinhold Company|year=1977|isbn=0-442-23240-3|page=464}}
2,3-Dihydroindene |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | 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 = {{ebicite|correct|EBI}} | ChEMBL = 370687 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C9H10/c1-2-5-9-7-3-6-8(9)4-1/h1-2,4-5H,3,6-7H2 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = PQNFLJBBNBOBRQ-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo=496-11-7 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = H9SCX043IG | PubChem=10326 | ChEBI_Ref = {{ebicite|correct|EBI}} | 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](/source/organic_compound) with the formula C9H10. It is a colorless liquid [hydrocarbon](/source/hydrocarbon). It is a [petrochemical](/source/petrochemical), a bicyclic compound. It occurs at the level of about 0.1% in [coal tar](/source/coal_tar). Many modified '''indanes''' are known. ==Production of indane skeleton== Indane itself is usually produced by hydrogenation of [indene](/source/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. {{doi|10.1002/14356007.a13_227}} More complex indanes are produced by cyclization of [phenylpropionic acid](/source/phenylpropionic_acid) and related compounds under [Friedel-Crafts reaction](/source/Friedel-Crafts_reaction) conditions. Such routes afford [1-indanone](/source/1-Indanone), which can be reduced to [indanol](/source/indanol) or the indane. 2-Bromoaryl derivatives with unsaturated substituents undergo [Heck reaction](/source/Heck_reaction)s ([palladium](/source/palladium)-catalyzed) involving formal loss of HBr and cyclization to indanes and indenes.{{cite journal |last1=Gabriele |first1=Bartolo |last2=Mancuso |first2=Raffaella |last3=Veltri |first3=Lucia |title=Recent Advances in the Synthesis of Indanes and Indenes |journal=Chemistry – A European Journal |date=2016 |volume=22 |issue=15 |pages=5056–5094 |doi=10.1002/chem.201503933 |pmid=26788795 |bibcode=2016ChEuJ..22.5056G }} [Enantioselective](/source/Enantioselective) routes to chiral indanes and indenes are also available.{{cite journal |last1=Borie |first1=Cyril |last2=Ackermann |first2=Lutz |last3=Nechab |first3=Malek |title=Enantioselective syntheses of indanes: From organocatalysis to C–H functionalization |journal=Chemical Society Reviews |date=2016 |volume=45 |issue=5 |pages=1368–1386 |doi=10.1039/c5cs00622h |pmid=26728953 }} Routes to the hydroindanes are also relevant.{{cite journal |last1=Hong |first1=Bor-Cherng |last2=Sarshar |first2=Sepehr |title=Recent Advances in the Synthesis of Indan Systems. A Review |journal=Organic Preparations and Procedures International |date=1999 |volume=31 |pages=1–86 |doi=10.1080/00304949909355675}} ==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.{{cite book |last1=Fiege |first1=Helmut |last2=Voges |first2=Heinz-Werner |last3=Hamamoto |first3=Toshikazu |last4=Umemura |first4=Sumio |last5=Iwata |first5=Tadao |last6=Miki |first6=Hisaya |last7=Fujita |first7=Yasuhiro |last8=Buysch |first8=Hans-Josef |last9=Garbe |first9=Dorothea |last10=Paulus |first10=Wilfried |title=Ullmann's Encyclopedia of Industrial Chemistry |chapter=Phenol Derivatives |date=2000 |doi=10.1002/14356007.a19_313 |isbn=978-3-527-30385-4 }} Many indanes can be prepared by reactions of indane with electrophiles, which attack the 5-position (on the benzene ring). For example, [sulfonation](/source/sulfonation) gives indane-5-sulfonic acid. Base hydrolysis of which gives 5-[indanol](/source/indanol).{{cite journal |title=(S)-Tetrahydro-1-Methyl-3,3-Diphenyl-1H,3H-Pyrrolo-[1,2-c][1,3,2]Oxazaborole-Borane Complex |journal=Organic Syntheses |date=1997 |volume=74 |page=50 |doi=10.15227/orgsyn.074.0050}} A family of indane derivatives are [empathogen-entactogen](/source/empathogen-entactogen)s. They are very close derivatives of other empathogen-entactogens such as [MDMA](/source/MDMA) and [MDA](/source/3%2C4-methylenedioxyamphetamine). Examples include [MDAI](/source/MDAI) and [MDMAI](/source/MDMAI).{{cite journal | pmid = 1967651| year = 1990| last1 = Nichols| first1 = D. E| title = Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA)| journal = Journal of Medicinal Chemistry| volume = 33| issue = 2| pages = 703–10| last2 = Brewster| first2 = W. K| last3 = Johnson| first3 = M. P| last4 = Oberlender| first4 = R| last5 = Riggs| first5 = R. M| doi=10.1021/jm00164a037}} Other derivatives include [2-aminoindane](/source/2-aminoindane), [NM-2-AI](/source/NM-2-AI) and the 5-iodo derivative [5-IAI](/source/5-IAI). File:Indinavir structure.svg|[Crixivan](/source/Crixivan) for treatment of [HIV/AIDS](/source/HIV%2FAIDS) File:Rasagiline2DCSD.svg|[Rasagiline](/source/Rasagiline) fortreatment of [Parkinson's disease](/source/Parkinson's_disease) '''Ramelteon''', sold under the brand name '''Rozerem''' among others, is a [melatonin agonist](/source/melatonin_agonist) [medication](/source/medication) which is used in the treatment of [insomnia](/source/insomnia) File:Ramelteon skeletal formula.svg|[Ramelteon](/source/Ramelteon) for treatment of [insomnia](/source/insomnia) File:5-APDI.svg|[5-APDI](/source/5-APDI) (c.f. [5-MAPDI](/source/5-MAPDI)) File:MDAI structure.svg|[5,6-methylenedioxy-2-aminoindane](/source/5%2C6-methylenedioxy-2-aminoindane), a recreational drug related to [MDMA](/source/MDMA) Indane can be used to prepare 5-propionylindane [63998-49-2].{{cite journal |author=Arnold, R. T. |author2=Barnes, R. A. | journal=Journal of the American Chemical Society | title=The Jacobsen Rearrangement. VIII. 1 Cyclic Systems; Mechanism | volume=66 | issue=6 | pages=960–964 | date= June 1944 | url=https://pubs.acs.org/doi/abs/10.1021/ja01234a036 | doi=10.1021/ja01234a036 | access-date=4 November 2025| url-access=subscription }} 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](/source/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, {{US patent|3882229}} (1975 to Nordmark Werke Gmbh). Another compound that is made from indane proper is called [Sulofenur](/source/Sulofenur) (LY181984) [110311-27-8].{{cite journal |author=Howbert, J. J. |author2=Grossman, C. S. |author3=Crowell, T. A. |author4=Rieder, B. J. |author5=Harper, R. W. |author6=Kramer, K. E. |author7=Tao, E. V. |author8=Aikins, J. |author9=Poore, G. A. | journal=Journal of Medicinal Chemistry | title=Novel agents effective against solid tumors: the diarylsulfonylureas. Synthesis, activities, and analysis of quantitative structure-activity relationships | volume=33 | issue=9 | pages=2393–2407 | date= September 1990 | url=https://pubs.acs.org/doi/abs/10.1021/jm00171a013 | doi=10.1021/jm00171a013| url-access=subscription }}Gerald A. Poore, {{US patent|5116874}} (1992 to Eli Lilly And Company). [Glyhexamide](/source/Glyhexamide) [451-71-8] is another example of such a compound prepared from indane starting material. [Glidazamide](/source/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](/source/Hydrogenation) of indane gives the saturated derivative [hydrindane](/source/hydrindane).{{citation|author=Norman L. Allinger, James L. Coke |date=1960 |doi=10.1021/ja01495a039 |issue=10 |pages=2553–2556 |periodical=[Journal of the American Chemical Society](/source/Journal_of_the_American_Chemical_Society) |title=The Relative Stabilities of cis and trans Isomers. VII. The Hydrindanes 1,2 |volume=82}} ==See also== * [Indene](/source/Indene) * [1,3-Indanedione](/source/1%2C3-Indanedione), a popular starting compound ==References== {{Reflist}} {{Authority control}} * --- Adapted from the Wikipedia article [Indane](https://en.wikipedia.org/wiki/Indane) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Indane?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.