ChemicalBook > CAS DataBase List > (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

Product Name
(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate
CAS No.
173604-87-0
Chemical Name
(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate
Synonyms
(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
Molecular Formula
C12H9NO8
Formula Weight
295.2
MOL File
173604-87-0.mol
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(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate Property

Boiling point:
434.8±55.0 °C(Predicted)
Density 
1.491
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H272May intensify fire; oxidizer

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P220Keep/Store away from clothing/…/combustible materials.

P370+P378In case of fire: Use … for extinction.

P501Dispose of contents/container to..…

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

Uses

(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).

Synthesis

(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 Preparation Products And Raw materials

Raw materials

Preparation Products

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

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173604-87-0, (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonateRelated Search:

1,4-Dioxane Barium carbonate DIOXOPROMETHAZINE HCL Ammonium carbonate Selenium dioxide TRIS(4-NITROPHENYL) PHOSPHATE Calcium carbonate Sodium carbonate Dimethyl carbonate dimethylsilanediol Methyl cyclopentenolone Methyl Cyclopentene Methyl bromide Carbonate POLY(BISPHENOL A CARBONATE) (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate

  • (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