Phthalazine

Phthalazine[1]
Names
	Preferred IUPAC name Phthalazine[2]
	Other names Benzo-orthodiazine; 2,3-Benzodiazine; Benzo[d]pyridazine
Identifiers
CAS Number	253-52-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	8852 ;
ECHA InfoCard	100.005.422
PubChem CID	9207;
UNII	91Y28DM24N ;
CompTox Dashboard (EPA)	DTXSID9049407 ;
	InChI InChI=1S/C8H6N2/c1-2-4-8-6-10-9-5-7(8)3-1/h1-6H Key: LFSXCDWNBUNEEM-UHFFFAOYSA-N ; InChI=1/C8H6N2/c1-2-4-8-6-10-9-5-7(8)3-1/h1-6H Key: LFSXCDWNBUNEEM-UHFFFAOYAE;
	SMILES C1=CC=C2C=NN=CC2=C1;
Properties
Chemical formula	C8H6N2
Molar mass	130.150 g·mol−1
Appearance	Pale yellow needles
Melting point	90 to 91 °C (194 to 196 °F; 363 to 364 K)
Boiling point	315 to 317 °C (599 to 603 °F; 588 to 590 K) (decomposition)
Solubility in water	Miscible
Acidity (pKa)	3.39[3]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

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 w-tetrabromorthoxylene with hydrazine, or by the reduction of chlorphthalazine with phosphorus and hydroiodic acid.[4]

Properties

It possesses basic properties and forms addition products with alkyl iodides.[4]

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.[4]

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References

Merck Index, 11th Edition, 7344.
Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 212. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
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.
One or more of the preceding sentences incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). "Phthalazines". Encyclopædia Britannica. 21 (11th ed.). Cambridge University Press. p. 545.

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[1] Merck Index, 11th Edition, 7344.

[iupac2013-2] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 212. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[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.

[EB1911-4] One or more of the preceding sentences incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). "Phthalazines". Encyclopædia Britannica. 21 (11th ed.). Cambridge University Press. p. 545.