1,4,7,10,13-Pentaoxa-16-azacyclooctadecan

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H315：Verursacht Hautreizungen.

  H319：Verursacht schwere Augenreizung.

  H335：Kann die Atemwege reizen.

• Sicherheit

  P261：Einatmen von Staub vermeiden.

  P264：Nach Gebrauch gründlich waschen.

  P264：Nach Gebrauch gründlich waschen.

  P271：Nur im Freien oder in gut belüfteten Räumen verwenden.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P302+P352：BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.

  P305+P351+P338：BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

1,4,7,10,13-Pentaoxa-16-azacyclooctadecane Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

• S-Sätze Betriebsanweisung:

  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
  S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

• Chemische Eigenschaften

  white to light yellow crystals or crystalline mass

• Verwenden

  1-Aza-18-crown-6 is used as building block for the synthesis of bis-crown ethers, lariat ethers and other monofunctionalized macrocycles. It is also used as pharmaceutical intermediate.

• Synthese

  

  37860-51-8

  

  111-42-2

  

  33941-15-0

  To a 3L three-necked round-bottomed flask was sequentially added a magnetic stirrer, 1.50 L of tert-butanol (tBuOH) and potassium tert-butanol (KOtBu, 30.7 g, 274 mmol). The mixture was heated to 40 °C with continuous stirring for 30 min to ensure complete dissolution of KOtBu. Subsequently, tetraethylene glycol di-p-toluenesulfonate (46 g, 91.5 mmol, dissolved in 100 mL of dioxane) and diethanolamine (9.6 g, 91.3 mmol, dissolved in 100 mL of tBuOH), respectively, were slowly added dropwise to the reaction system over a period of 2 hours through two different dropping funnels. Note: The rate of titration has a significant effect on the reaction yield, and slow titration helps to increase the yield. After dropwise addition, the reaction mixture was continued to be stirred for 1 hour and subsequently cooled to room temperature. The reaction mixture was filtered through a Brinell funnel and the solvent was removed by rotary evaporator. To the residual brown viscous mass was added 100 mL of deionized water and extracted first with hexane (1 x 60 mL, discarding the hexane phase) and then with dichloromethane (CH2Cl2, 5 x 60 mL). The dichloromethane phases were combined, dried with anhydrous magnesium sulfate (MgSO4) and the solvent was again removed by rotary evaporator. The resulting dark brown residue was distilled under high vacuum through a ball-bulb distillation apparatus using a hot air gun for assisted heating, resulting in the colorless liquid-like product az-18-crown ether-6 (8.4 g, 35% yield). The nuclear magnetic resonance (NMR) spectrum of the product was consistent with the data reported in the literature. It was found that the tBuOH used in the reaction could be recovered by distillation and used in the subsequent synthesis of aza-crown ether even though it contained a small amount of dioxane (<5%).

• Einzelnachweise

  [1] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 1, p. 212 - 218
  [2] Polyhedron, 2018, vol. 141, p. 385 - 392
  [3] Phosphorus, Sulfur and Silicon and the Related Elements, 2006, vol. 181, # 1, p. 219 - 225
  [4] Journal of the Chemical Society, Chemical Communications, 1981, # 10, p. 471 - 472

1,4,7,10,13-Pentaoxa-16-azacyclooctadecane Upstream-Materialien And Downstream Produkte

1,4,7,10,13-Pentaoxa-16-azacyclooctadecan Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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