BIS(2,4-DINITROPHENYL) CARBONATE Property

Melting point:

148 °C(Solv: benzene (71-43-2))

Boiling point:

583.5±50.0 °C(Predicted)

Density 

1.741±0.06 g/cm3(Predicted)

solubility 

sol EtOAc, pyridine, DMF, CHCl3; moderately sol benzene; insol hexane; dec hot H2O, EtOH

color 

yellow solid

Hazard and Precautionary Statements (GHS)

BIS(2,4-DINITROPHENYL) CARBONATE Chemical Properties,Usage,Production

Description

Bis(2,4-dinitrophenyl)carbonate is used in the preparation of azapeptides.

Uses

Peptide and azapeptide coupling reagent that functions by activating amines, forming derivatives suitable for condensation with N-protected amino acids; converts carboxylic acids to activated esters.

Synthesis

Diphenyl carbonate (20 g) is added to a stirred mixture of conc HNO3 (100 mL) and conc H2SO4 (120 mL) at 50-55 °C over 1 h. The resulting suspension is stirred at 50 °C for 3 h, left at rt for 90 h and poured onto ice. The precipitate is washed with iced water and dried in vacuo over P2O5. This affords bis(2,4-dinitrophenyl) carbonate (31.2 g, 85%) which recrystallizes from hexane/benzene giving crystals, mp 144-146 °C.

Precautions

Store in a cool dry place to preclude contact with moisture; the hazardous and toxicological properties have not been investigated; may explode if heated rapidly