Bismole
title: "Bismole" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["bismuth-heterocycles", "metalloles", "hypothetical-chemical-compounds"] topic_path: "science/chemistry" source: "https://en.wikipedia.org/wiki/Bismole" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
| verifiedrevid = 415222393 | ImageFileL1 = bismole.png | ImageSizeL1 = 80 | ImageAltL1 = Skeletal formula of bismole | ImageFileR1 = Bismole-3D-balls.png | ImageSizeR1 = 150 | ImageAltR1 = Ball-and-stick model of the bismole molecule | PIN = 1H-Bismole | OtherNames = |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo = 89067-15-2 | ChemSpiderID_Ref = | ChemSpiderID = 24751865 | PubChem = 18969921 | SMILES = C1=C[BiH]C=C1 | StdInChI_Ref = | StdInChI=1S/C4H4.Bi.H/c1-3-4-2;;/h1-4H;; | StdInChIKey_Ref = | StdInChIKey = SUILZFJIVIXVOA-UHFFFAOYSA-N |Section2={{Chembox Properties | C=4 | H=5 | Bi=1 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} |Section8={{Chembox Related | OtherCompounds = Pyrrole, phosphole, arsole, stibole}}
Bismole is a theoretical heterocyclic organic compound, a five-membered ring with the formula C4H4BiH. It is classified as a metallole. It can be viewed as a structural analog of pyrrole, with bismuth replacing the nitrogen atom of pyrrole. The unsubstituted compound has not been isolated due to the high energy of the Bi-H bond. Substituted derivatives, which have been synthesized, are called bismoles.{{Citation | last1 = Suzuki | first1 = Hitomi | first2 = Naoki | last2 = Komatsu | first3 = Takuji | last3 = Ogawa | first4 = Toshihiro | last4 = Murafuji | first5 = Tohru | last5 = Ikegami | first6 = Yoshihiro | last6 = Matano | year = 2001 | title = Organobismuth Chemistry | publisher = Elsevier | pages = 329–344 | chapter = 4: Bismuth-Containing Heterocycle | isbn = 978-0-444-20528-5 | chapter-url = https://books.google.com/books?id=qODswAbaBmsC&pg=PA329
Reactions
2,5-Bis(trimethylsilyl)-3,4-dimethyl-1-phenyl-1H-bismole, for example, can be formed by the reaction of (1Z,3Z)-1,4-bis(trimethylsilyl)-1,4-diiodobuta-2,3-dimethyl-1,3-diene and diiodophenylbismuthine. Bismoles can be used to form ferrocene-like sandwich compounds.{{cite book | chapter = 4.22.7 – Functions Containing Arsenic, Antimony or Bismuth with a Metalloid, R12C=C(AsR22)SiR33 etc | first = John M. | last = Berge | editor1-last = Katritzky | editor1-first = Alan R. | editor-link1 = Alan R. Katritzky | editor2-last = Meth-Cohn | editor2-first = Otto | editor3-last = Rees | editor3-first = Charles W. | editor-link3 = Charles Rees | editor4-first = Gordon W. | editor4-last = Kirby | year = 1995 | title = Synthesis: Carbon with Two Heteroatoms, Each Attached by a Single Bond | series = Comprehensive Organic Functional Group Transformations | volume = 4 | publisher = Elsevier | pages = 1038–1040 | isbn = 978-0-08-042325-8 | chapter-url = https://books.google.com/books?id=0RQEsfYCuBcC&pg=PA1038
References
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