Phthalazine

chembox
Reference= ["Merck Index", 11th Edition, 7344.]
ImageFile=Phthalazin - Phthalazine.svg
ImageSize=180px
IUPACName=Phthalazine
OtherNames=Benzo-orthodiazine
2,3-Benzodiazine
Benzo ["d"] pyridazine
Section1=Chembox Identifiers
CASNo=253-52-1
PubChem=9207
SMILES=C1=CC=C2C=NN=CC2=C1
Section2=Chembox Properties
Formula=C₈H₆N₂
MolarMass=130.15 g/mol
Appearance=Pale yellow needles
Density=
MeltingPt=90-91 °C
BoilingPt=315-317 °C (decomposition)
Solubility=Miscible
Section3=Chembox Hazards
MainHazards=
FlashPt=
Autoignition=

Phthalazine, also called benzo-orthodiazine or benzopyridazine, is a heterocyclic organic compound with the molecular formula C₈H₆N₂. It is isomeric with the cinnoline. Phthalazine can be obtained by the condensation of w-tetrabromorthoxylene with hydrazine, or by the reduction of chlorphthalazine with phosphorus and hydroiodic acid. It possesses basic properties and forms addition products with alkyl iodides. 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.

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