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4-Nitrophenyl chloroformate is used in the synthesis of poly(oxyethylene) modified dextrans. It is also used to prepare a cleavable, heterobifunctional cross-linker for reversible conjugation of amines to thiol-modified DNA. Further, it is used in the synthesis of mixed, activated carbonates, thiocarbonates and activated urethanes. In addition to this, it is used in the preparation of 4-nitrophenyl diazoacetate with diazomethane.
Reagent for protection of nucleoside alcohols. The carbonate derivatives readily undergo aqueous hydrolysis in the presence of imidazole: J. Org. Chem., 33, 3699 (1967). For use in the formation of a carbonate linker in an efficient N-terminal attachment methodology for solid phase peptide synthesis, see: Synlett, 1609 (2000).
Sarma, B. K.; Liu, X.; Wu, H.; Gao, Y.; Kodadek, T. Solid phase synthesis of 1,3,4-oxadiazin-5 (6R)-one and 1,3,4-oxadiazol-2-one scaffolds from acyl hydrazides. Org. Biomol. Chem. 2015, 13 (1), 59-63.
Lee, N. R.; Zhang, X.; Darna, M.; Dwoskin, L. P.; Zheng, G. Muscarinic acetylcholine receptor binding affinities of pethidine analogs. Bioorg. Med. Chem. Lett. 2015, 25 (22), 5032-5035.
Hazard Statements: H302-H314-H318-H335
Harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage. May cause respiratory irritation.
Precautionary Statements: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a
IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.