74401-81-3

Basic information

• Product Name: N-(4-nitrophenyl)carbamate ion
• Synonyms: N-(4-nitrophenyl)carbamate ion
• CAS NO: 74401-81-3
• Molecular Weight: 181.128
• Mol File: 74401-81-3.mol

Chemical Properties

• CAS DataBase Reference: N-(4-nitrophenyl)carbamate ion(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-nitrophenyl)carbamate ion(74401-81-3)
• EPA Substance Registry System: N-(4-nitrophenyl)carbamate ion(74401-81-3)

Safety Data

• Hazardous Substances Data: 74401-81-3(Hazardous Substances Data)

Upstream product

• 50882-33-2 (4-nitro-phenyl)-carbamic acid-(2-methoxy-ethyl ester) 
• 124-38-9 carbon dioxide 
• 100-01-6 4-nitro-aniline 
• 405-59-4 (4-nitro-phenyl)-carbamic acid-(2,2,2-trifluoro-ethyl ester) 
• 1943-87-9 methyl N-(4-nitrophenyl)carbamate 

Downstream Products

• 100-01-6 4-nitro-aniline 

Relevant articles and documents

Unlocking the potential of phenacyl protecting groups: CO2-based formation and photocatalytic release of caged amines

Orthogonal protection and deprotection of amines remain important tools in synthetic design as well as in chemical biology and material research applications. A robust, highly efficient, and sustainable method for the formation of phenacyl-based carbamate esters was developed using CO2 for the in situ preparation of the intermediate carbamates. Our mild and broadly applicable protocol allows for the formation of phenacyl urethanes of anilines, primary amines, including amino acids, and secondary amines in high to excellent yields. Moreover, we demonstrate the utility by a mild and convenient photocatalytic deprotection protocol using visible light. A key feature of the [Ru(bpy)3](PF6)2-catalyzed method is the use of ascorbic acid as reductive quencher in a neutral, buffered, two-phase acetonitrile/water mixture, granting fast and highly selective deprotection for all presented examples.

Micellar Catalysis of Organic Reactions. XII. Basic Hydrolysis of Some Alkyl and Aryl N-(4-Nitrophenyl)carbamates

The basic hydrolysis of a number of alkyl and aryl N-(4-nitrophenyl)carbamates in the presence and absence of micelles of cetyltrimethylammonium bromide (ctab) are reported.In water the stable product at 26 deg C was N-(4-nitrophenyl)carbamate ion (3).At higher temperatures this carbamate ion slowly decomposed to 4-nitroaniline.In ctab the decarboxylation of the N-(4-nitrophenyl)carbamate ion was strongly catalysed (x 45) and thus the observed final product even at 26 deg C was 4-nitroaniline.Kinetic studies in water end in ctab were consistent with decomposition of the methyl carbamate (1a) by a BAC2 mechanism and the 2,2,2-trifluoroethyl carbamate (1c) by an E1cB mechanism.The extent of ionization of the substrate carbamates to nitranion (4) was enhanced in ctab as was the rate of spontaneous decomposition of the nitranion.This is in contrast to other E1cB reactions reported in the literature, for which the rate of spontaneous decomposition of the carbanion was inhibited by ctab.For compounds reacting by the BAC2 mechanism, the tetrahedral intermediate (2) partitioned in favour of C-OR bond breaking rather than C-N bond breaking observed previously for some N-methyl derivatives.