CAS 5070-13-3: Bis(4-nitrophenyl) carbonate

Bis(4-nitrophenyl) carbonate

This Thermo Scientific Chemicals brand product was originally part of the Acros Organics product portfolio. Some documentation and label information may refer to the legacy brand. The original Acros Organics product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Bis(4-nitrophenyl) carbonate is used as a reagent for preparation of symmetrical and unsymmetrical urea and 4-nitrophenyl esters of N-protected amino acids. It acts as a peptide coupling reagent. It finds application as a reagent for the preparation of carbamate linked cytosines. This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications Bis(4-nitrophenyl) Carbonate, is used for synthesis of 4-nitrophenyl active esters of amino acids. It can also be used in the preparation of symmetrical and unsymmetrical ureas. References Turoczi, M., et al.: Molecules, 13(12), 3192-3197 (2008); Cavallaro, G., et al.: Nanomedicine, 4(3), 291-303 (2009);

4-Nitrophenyl carbonate is an activated form of the 4-nitrophenol molecule. It is a reactive compound that has been shown to react with hydroxyl groups on lysine residues in proteins and amino acids, as well as carbonate groups on fatty acids. The reaction mechanism of 4-nitrophenyl carbonate is not fully understood, but it is thought to involve a nucleophilic attack by the hydroxyl group on the carbonyl carbon atom. This reaction causes an addition of water and formation of a new bond, which can be hydrolyzed back to the starting material. The synthesis methods for 4-nitrophenyl carbonate include amines and the activation of phenols with sodium or potassium hydroxide. The reactivity of this molecule can be enhanced using fatty acid esters such as methyl oleate or glycosides such as glucosamine hydrochloride.