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{{Short description|Chemical compound}} {{chembox | Watchedfields = changed | verifiedrevid = 443869434 | Name = Imidazole | ImageFileL1 = Imidazole 2D full aromatic.svg | ImageClassL1 = skin-invert-image | ImageAltL1 = Full structural formula | ImageFileR1 = Imidazole 2D numbered.svg | ImageClassR1 = skin-invert-image | ImageAltR1 = Skeletal formula with numbers | ImageFileL2 = Imidazole-3D-balls.png | ImageClassL2 = bg-transparent | ImageAltL2 = Ball-and-stick model | ImageFileR2 = Imidazole-3D-spacefill.png | ImageClassR2 = bg-transparent | ImageAltR2 = Space-filling model | ImageFile3 = Sample of Imidazole.jpg | PIN = 1''H''-Imidazole<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 140 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref> | SystematicName = | OtherNames = 1,3-Diazole<br/>Glyoxaline (archaic) | Section1 = {{Chembox Identifiers | CASNo = 288-32-4 | CASNo_Ref = {{cascite|correct|CAS}} | Beilstein = 103853 | Gmelin = 1417 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 773 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 16069 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 540 | DrugBank = DB03366 | EINECS = 206-019-2 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C01589 | InChI = 1/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5) | PubChem = 795 | RTECS = NI3325000 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 7GBN705NH1 | UNNumber = 3263 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = RAXXELZNTBOGNW-UHFFFAOYSA-N | SMILES = c1cnc[nH]1 }} | Section2 = {{Chembox Properties | Formula = C<sub>3</sub>H<sub>4</sub>N<sub>2</sub> | MolarMass = 68.077 g/mol | Appearance = White or pale yellow solid | Density = 1.23 g/cm<sup>3</sup>, solid | Solubility = 633 g/L | LambdaMax = 206 nm | MeltingPtC = 89 to 91 | MeltingPt_notes = | BoilingPtC = 256 | BoilingPt_notes = | pKa = 6.95 (for the [[conjugate acid]]) <ref>{{cite journal|last1=Walba|first1=H.|last2=Isensee|first2=R. W.|title=Acidity constants of some arylimidazoles and their cations|journal=J. Org. Chem.|volume=26|issue=8|pages=2789β2791|date=1961|doi=10.1021/jo01066a039}}</ref> }} | Section3 = {{Chembox Structure | Coordination = Planar 5-membered ring | CrystalStruct = [[Monoclinic]] | Dipole = 3.61 [[Debye|D]] }} | Section7 = {{Chembox Hazards | MainHazards = Corrosive | FlashPtC = 146 | GHS_ref=<ref>{{cite web |title=Imidazole |url=https://pubchem.ncbi.nlm.nih.gov/compound/795#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=17 February 2024 |language=en |archive-date=10 May 2023 |archive-url=https://web.archive.org/web/20230510184350/https://pubchem.ncbi.nlm.nih.gov/compound/795#section=Safety-and-Hazards |url-status=live }}</ref> | GHSPictograms = {{GHS05}}{{GHS07}}{{GHS08}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|302|314|360D}} | PPhrases = {{P-phrases|263|270|280|301+310|305+351+338|308+313}}<ref>{{cite web| publisher=Molekula Group| website=molekula.com| url=https://molekula.com/catalog/288-32-4/21611083-Imidazole| title=Imidazole| access-date=2018-10-19| archive-date=2018-10-19| archive-url=https://web.archive.org/web/20181019164240/https://molekula.com/catalog/288-32-4/21611083-Imidazole| url-status=live}}</ref> }} }} '''Imidazole''' (ImH) is an [[organic compound]] with the formula {{chem2|(CH)3(NH)N}}. It is a white or colourless solid that is soluble in water, producing a mildly [[alkali]]ne solution. It can be classified as a [[heterocycle]], specifically as a [[diazole]]. Many natural products, especially [[alkaloid]]s, contain the imidazole ring. These imidazoles share the 1,3-C<sub>3</sub>N<sub>2</sub> ring but feature varied substituents. This ring system is present in important biological building blocks, such as [[histidine]] and the related hormone [[histamine]]. Many drugs contain an imidazole ring, such as certain [[antifungal drug]]s, the [[nitroimidazole]] series of [[antibiotics]], and the sedative [[midazolam]].<ref>{{cite book|author-link=Alan R. Katritzky|last1=Karitzky|first1=A. R.|last2=Rees| first2=C.W.R.| last3=Scriven| first3=E.F.V.|title=Comprehensive Heterocyclic Chemistry|volume=5|pages=469β498|date=1984| isbn=978-0-08-042072-1}}</ref><ref>{{cite book|last=Grimmett|first=M. Ross|title=Imidazole and Benzimidazole Synthesis|publisher=Academic Press|date=1997|isbn=978-0-08-053445-9}}</ref><ref>{{cite book|last=Brown|first=E. G.|title=Ring Nitrogen and Key Biomolecules|publisher=Kluwer Academic Press|date=1998| isbn=978-94-011-4906-8}}</ref><ref>{{cite book|last=Pozharskii|first=A. F.|display-authors=etal|title=Heterocycles in Life and Society|publisher=John Wiley & Sons|date=1997| isbn=978-0-471-96033-1}}</ref><ref>{{cite book|title=Heterocyclic Chemistry|first=T. L.|last=Gilchrist|publisher=Bath Press|date=1985|isbn=978-0-582-01421-3}}</ref> When fused to a [[pyrimidine]] ring, it forms a [[purine]], which is the most widely occurring nitrogen-containing [[Heterocyclic compound|heterocycle]] in nature.<ref>{{cite journal |last= Rosemeyer |first= H. |year= 2004 |title= The Chemodiversity of Purine as a Constituent of Natural Products |journal= Chemistry & Biodiversity |volume= 1 |issue= 3 |pages= 361β401 |doi= 10.1002/cbdv.200490033|pmid= 17191854 |s2cid= 12416667 }}</ref> The name "imidazole" was coined in 1887 by the German chemist [[Arthur Rudolf Hantzsch]] (1857β1935).<ref>Hantzsch, A. and Weber, J. H. (1887) [https://babel.hathitrust.org/cgi/pt?id=hvd.cl1hzr;view=1up;seq=872 "Ueber Verbindungen des Thiazols (Pyridins der Thiophenreihe)"] {{Webarchive|url=https://web.archive.org/web/20200530234013/https://babel.hathitrust.org/cgi/pt?id=hvd.cl1hzr&view=1up&seq=872 |date=2020-05-30 }} (On compounds of thiazole (pyridines of the thiophene series), ''Berichte der deutschen chemischen Gesellschaft'', '''20''' : 3118β3132, see p. 3119. See also: Hantzsch, A. (1888) [https://babel.hathitrust.org/cgi/pt?id=uiug.30112025844876;view=1up;seq=13 "Allegemeine Bemerkungen ΓΌber Azole"] {{Webarchive|url=https://web.archive.org/web/20200530234010/https://babel.hathitrust.org/cgi/pt?id=uiug.30112025844876&view=1up&seq=13 |date=2020-05-30 }} (General observations about azoles), ''Annalen der Chemie'', '''249''' : 1β6. Hantzsch proposed a reform of the nomenclature of azole compounds, including a proposal to call the heterocyclic ring C<sub>3</sub>H<sub>3</sub>(NH)N "imidazole"; see pp. 2 and 4.</ref>
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