4,4'-Diacetamidodiphenylether

Strukturformel
Strukturformel von 4,4'-Diacetamidodiphenylether
Allgemeines
Name 4,4'-Diacetamidodiphenylether
Andere Namen
  • 4,4'-Oxybisacetanilid
  • Paracetamol Impurity N
  • Acetaminophen Impurity
Summenformel C16H16N2O3
Kurzbeschreibung

weißer Feststoff[1]

Externe Identifikatoren/Datenbanken
CAS-Nummer 3070-86-8
PubChem 95125
ChemSpider 85836
Wikidata Q83055664
Eigenschaften
Molare Masse 284,31 g·mol−1
Aggregatzustand

fest[1]

Schmelzpunkt

228–231 °C[1]

Löslichkeit

schwer löslich in DMSO und Methanol[1]

Sicherheitshinweise
GHS-Gefahrstoffkennzeichnung[2]
keine GHS-Piktogramme

H- und P-Sätze H: keine H-Sätze
P: keine P-Sätze[2]
Soweit möglich und gebräuchlich, werden SI-Einheiten verwendet.
Wenn nicht anders vermerkt, gelten die angegebenen Daten bei Standardbedingungen (0 °C, 1000 hPa).

4,4'-Diacetamidodiphenylether ist eine chemische Verbindung aus der Gruppe der Diphenylether und der Anilide.

Gewinnung und Darstellung

4,4'-Diacetamidodiphenylether kann durch Reaktion von 4,4'-Diaminodiphenylether mit Acetanhydrid in Eisessig hergestellt werden.[3]

Eigenschaften

4,4'-Diacetamidodiphenylether ist ein weißer Feststoff, der schwer löslich in DMSO und Methanol ist.[1] Die Verbindung kann als Verunreinigung in Paracetamol nachgewiesen werden.[4]

Verwendung

4,4'-Diacetamidodiphenylether ist ein chemisches Reagenz, das bei der Synthese lichtempfindlicher Polymerverbindungen und bei optischen Anwendungen eingesetzt wird. Es wird auch bei der Herstellung von Benzimidazol-Derivaten verwendet, die durch Apoptose Anti-Tumor-Aktivität zeigen.[1]

Einzelnachweise

  1. ↑ a b c d e f Eintrag zu Bis(p-acetylaminophenyl) Ether bei Toronto Research Chemicals, abgerufen am 12. Oktober 2023 (PDF).
  2. ↑ a b Datenblatt N-(4-(4-ACETYLAMINO-PHENOXY)-PHENYL)-ACETAMIDE bei Sigma-Aldrich, abgerufen am 1. Januar 2024 (PDF).
  3. ↑ Patent DE1768478A1: 3,3'-Dichlor-4,4'-diaminodiphenyläther. Angemeldet am 17. Mai 1968, veröffentlicht am 18. November 1971, Anmelder: Farbenfabriken Bayer AG, Erfinder: Walter Meckel. Erwin Müller.‌
  4. ↑ Cemil Caner Arıkan, Necla Kulabaş, İlkay Küçükgüzel: Synthesis and standardization of an impurity of acetaminophen, development and validation of liquid chromatographic method. In: Journal of Pharmaceutical and Biomedical Analysis. Band 223, 2023, S. 115123, doi:10.1016/j.jpba.2022.115123.

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