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(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate

(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate Struktur
173604-87-0
CAS-Nr.
173604-87-0
Englisch Name:
(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate
Synonyma:
(5-Methyl-2-oxo-1,3-dioxol-4-yl)methylp-nitrophenyl carbonate;(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate;(5-methyl-2-oxo-1,3-dioxopentene-4-yl) methyl 4-nitrophenyl carbonate;Carbonic acid, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl -ester;carbonic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester 4-nitro-phenyl ester
CBNumber:
CB01876499
Summenformel:
C12H9NO8
Molgewicht:
295.2
MOL-Datei:
173604-87-0.mol

(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate Eigenschaften

Siedepunkt:
434.8±55.0 °C(Predicted)
Dichte
1.491
InChI
InChI=1S/C12H9NO8/c1-7-10(21-12(15)19-7)6-18-11(14)20-9-4-2-8(3-5-9)13(16)17/h2-5H,6H2,1H3
InChIKey
MZGIKNSLLFWGKL-UHFFFAOYSA-N
SMILES
C(OC1=CC=C([N+]([O-])=O)C=C1)(=O)OCC1=C(C)OC(=O)O1
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Bildanzeige (GHS) Flame Over Circle (GHS03)Environment (GHS09)
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H272 Kann Brand verst?rken; Oxidationsmittel. Oxidierende Flüssigkeiten (Kapitel 2.13), Kategorie 2 (Ox. Liq. 2), H272 Oxidierende Flüssigkeiten (Kapitel 2.13), Kategorie 2 Achtung
Warnung
P210, P220, P221P280, P370+P378,P501
H411 Giftig für Wasserorganismen, mit langfristiger Wirkung. Langfristig (chronisch) gew?ssergef?hrdend Kategorie 2
Sicherheit
P210 Von Hitze, hei?en Oberfl?chen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.
P220 Von Kleidung und anderen brennbaren Materialien fernhalten.
P370+P378 Bei Brand: zum L?schen verwenden.
P501 Inhalt/Beh?lter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate Chemische Eigenschaften,Einsatz,Produktion Methoden

Verwenden

(5-Methyl-2-oxo-1,3-dioxol-4-YL)methyl 4-nitrophenyl carbonate is a pharmaceutical intermediate compound for the preparation of Ceftobiprole medocaril, a broad-spectrum, 5th generation cephalosporin with activity against gram-positive bacteria (e.g. methicillin-resistant).

Synthese

(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate is prepared by the reaction of 4-Nitrophenyl chloroformate and Bis(4-nitrophenyl) carbonate. The specific synthesis steps are as follows:
4-Hydroxymethyl-5-methyl-1,3-doxolene-2-one (5.59 g) and pyridine (3.74 g) were dissolved in 50 mL of chloroform and cooled in an ice bath. 4-Nitrophenylchloroformate (9.46 g) dissolvedin chloroform (50 mL) was added dropwise to the above solution. The mixture was stirred for 16 hours at room temperature. The reaction mixture was cooled in ice and washed with ice cold 1percent sodium hydroxide, 1N hydrochloric acid, water and brine and dried over sodium sulfate. Evaporation of the organic layer resulted in 11.2 g of crude product, which was crystallized from chloroform/hexane. The crystals formed were filtered and washed with ice cold hexane/chloroform (1:1), to obtain the pure 4-nitrophenyl carbonate (9.11 g, 81percent); mp 116°-117°; 1 H NMR (CDCl3) δ2.23 (s, 3H), 5.05 (s,2H), 7.41 (d, 2H), 8.3 (s, 2H); 13 C NMR (CDCl3), δ9.43, 58.07, 121.69, 121.35, 132.15, 141.42, 145.57, 151.66, 152.19, 155.05; IR (KBr) 1779, 1811, 1525, 1247, 1221, 1207 cm-1.
(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate synthesis

(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

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173604-87-0()Verwandte Suche:


  • (5-Methyl-2-oxo-1,3-dioxol-4-yl)methylp-nitrophenyl carbonate
  • (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate
  • Carbonic acid, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl -ester
  • carbonic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester 4-nitro-phenyl ester
  • (5-methyl-2-oxo-1,3-dioxopentene-4-yl) methyl 4-nitrophenyl carbonate
  • 173604-87-0
  • C12H9NO8
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