Phthalazin

Strukturformel
Strukturformel von Phthalazin
Allgemeines
Name Phthalazin
Andere Namen
  • 2,3-Benzodiazin
  • 2,3-Diazanaphthalin
  • Benzo[d]pyridazin
  • Benzo-orthodiazin
Summenformel C8H6N2
Kurzbeschreibung

blassgelber Feststoff[1]

Externe Identifikatoren/Datenbanken
CAS-Nummer 253-52-1
EG-Nummer 205-963-2
ECHA-InfoCard 100.005.422
PubChem 9207
ChemSpider 8852
Wikidata Q6593919
Eigenschaften
Molare Masse 130,15 g·mol−1
Aggregatzustand

fest[1]

Schmelzpunkt

89–92 °C[1]

Siedepunkt

317 °C[1]

Löslichkeit
  • löslich in Wasser[1]
  • löslich in organischen Lösungsmitteln[2]
Sicherheitshinweise
GHS-Gefahrstoffkennzeichnung[3]
Gefahrensymbol

Achtung

H- und P-Sätze H: 341
P: 280[3]
Soweit möglich und gebräuchlich, werden SI-Einheiten verwendet.
Wenn nicht anders vermerkt, gelten die angegebenen Daten bei Standardbedingungen (0 °C, 1000 hPa).

Phthalazin ist eine organische Verbindung, die zu den Heterocyclen (genauer: Heteroaromaten und Diazanaphthalinen) zählt. Die Verbindung besteht aus einem Benzolring, an dem ein Pyridazinring anelliert ist. Phthalazin ist isomer zu Chinazolin, Chinoxalin und Cinnolin.

Gewinnung und Darstellung

Phthalazin kann durch Kondensation von ω-Tetrabromorthoxylol mit Hydrazin oder durch Reduktion von Chlorphthalazin mit Phosphor und Iodwasserstoff gewonnen werden.[4] Ebenfalls möglich ist die Darstellung durch Oxidation von 1-Hydrazinophthalazin.[2]

Eigenschaften

Phthalazin ist ein blassgelber Feststoff, der löslich in Wasser ist.[1] Es besitzt basische Eigenschaften und bildet Additionsprodukte mit Alkyliodiden.[4] Phthalazin und seine Derivate kommen nicht in der Natur vor.[2]

Verwendung

Phthalazin wird als Ausgangsprodukt für verschiedene organischen Synthesen verwendet.[5]

Einzelnachweise

  1. ↑ a b c d e f Datenblatt Phthalazine, 98% bei Alfa Aesar, abgerufen am 12. Juni 2013 (Seite nicht mehr abrufbar).
  2. ↑ a b c Raymond N. Castle: The Chemistry of Heterocyclic Compounds, Condensed Pyridazines Including … John Wiley & Sons, 2009, ISBN 0-470-18848-0, S. 324 ff. (eingeschränkte Vorschau in der Google-Buchsuche).
  3. ↑ a b Datenblatt Phthalazine, 98% bei Sigma-Aldrich, abgerufen am 10. November 2021 (PDF).
  4. ↑ a b Phthalazines. In: Encyclopædia Britannica. 11. Auflage. Band 21: Payn – Polka. London 1911, S. 545 (englisch, Volltext [Wikisource]).
  5. ↑ Desmond J. Brown, Jonathan A. Ellman, Edward C. Taylor: Cinnolines and Phthalazines: Chemistry of Heterocyclic Compounds, Supplement II. John Wiley & Sons, 2005, ISBN 0-471-74411-5, S. 175 (eingeschränkte Vorschau in der Google-Buchsuche).

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