Phthalazine

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

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 440002476 | Reference = | ImageFile = Phthalazin - Phthalazine.svg | ImageSize = 180 | ImageAlt = Skeletal formula of phthalazine | ImageFile1 = Phthalazine-3D-balls.png | ImageSize1 = 180 | ImageAlt1 = Ball-and-stick model of the phthalazine molecule | PIN = Phthalazine | OtherNames = Benzo-orthodiazine 2,3-Benzodiazine Benzo[d]pyridazine |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo=253-52-1 | UNII_Ref = | UNII = 91Y28DM24N | PubChem = 9207 | ChemSpiderID_Ref = | ChemSpiderID = 8852 | SMILES = C1=CC=C2C=NN=CC2=C1 | InChI = 1/C8H6N2/c1-2-4-8-6-10-9-5-7(8)3-1/h1-6H | InChIKey = LFSXCDWNBUNEEM-UHFFFAOYAE | StdInChI_Ref = | StdInChI = 1S/C8H6N2/c1-2-4-8-6-10-9-5-7(8)3-1/h1-6H | StdInChIKey_Ref = | StdInChIKey = LFSXCDWNBUNEEM-UHFFFAOYSA-N |Section2={{Chembox Properties | C=8|H=6|N=2 | Appearance = Pale yellow needles | Density= | MeltingPtC = 90 to 91 | BoilingPtC = 315 to 317 | BoilingPt_notes= (decomposition) | Solubility = Miscible | pKa=3.39 |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt =

Phthalazine, also called benzo-orthodiazine or benzopyridazine, is a heterocyclic organic compound with the molecular formula C8H6N2. It is isomeric with other naphthyridines including quinoxaline, cinnoline and quinazoline.

Synthesis

Phthalazine can be obtained by the condensation of ω-tetrabromorthoxylene with hydrazine, or by the reduction of chlorphthalazine with phosphorus and hydroiodic acid.

Properties

It possesses basic properties and forms addition products with alkyl iodides.

Reactions

Upon oxidation with alkaline potassium permanganate it yields pyridazine dicarboxylic acid. Zinc and hydrochloric acid decompose it with formation of orthoxylylene diamine. The keto-hydro derivative phthalazone (C8H6ON2), is obtained by condensing hydrazine with orthophthalaldehydoacid. On treatment with phosphorus oxychloride, it yields a chlorphthalazine, which with zinc and hydrochloric acid gives isoindole (C8H7N), and with tin and hydrochloric acid, phthalimidine (C8H7ON), the second nitrogen atom being eliminated as ammonia.

References

References

  1. ''[[Merck Index]]'', 11th Edition, '''7344'''.
  2. (2014). "Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
  3. Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., ''Determination of Organic Structures by Physical Methods'', Academic Press, New York, 1955.
  4. {{EB1911

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phthalazinessimple-aromatic-rings