Phthalazine
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Names | |
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Preferred IUPAC name
Phthalazine[2] | |
Other names
Benzo-orthodiazine
2,3-Benzodiazine Benzo[d]pyridazine | |
Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.005.422 |
PubChemCID
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UNII | |
CompTox Dashboard(EPA)
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Properties | |
C8H6N2 | |
Molar mass | 130.150g·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) |
Miscible | |
Acidity(pKa) | 3.39[3] |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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Phthalazine,also called benzo-orthodiazine or benzopyridazine, is aheterocyclicorganic compoundwith the molecular formula C8H6N2.It isisomericwith othernaphthyridinesincludingquinoxaline,cinnolineandquinazoline.
Synthesis
[edit]Phthalazine can be obtained by thecondensationof w-tetrabromorthoxylene withhydrazine,or by thereductionof chlorphthalazine withphosphorusandhydroiodic acid.[4]
Properties
[edit]It possessesbasicproperties and forms addition products withalkyl iodides.[4]
Reactions
[edit]Upon oxidation withalkalinepotassium permanganateit yieldspyridazine dicarboxylic acid.Zincandhydrochloric aciddecompose it with formation of orthoxylylene diamine. The keto-hydro derivativephthalazone(C8H6ON2), is obtained by condensing hydrazine with orthophthalaldehydoacid[citation needed].On treatment withphosphorus oxychloride,it yields a chlorphthalazine, which withzincandhydrochloric acidgives isoindole (C8H7N), and withtinand hydrochloric acid, phthalimidine (C8H7ON), the secondnitrogenatombeing eliminated asammonia.[4]
References
[edit]- ^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.ISBN978-0-85404-182-4.
- ^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.
- ^abcpublic domain:Chisholm, Hugh,ed. (1911). "Phthalazines".Encyclopædia Britannica.Vol. 21 (11th ed.). Cambridge University Press. p. 545. One or more of the preceding sentences incorporates text from a publication now in the