92491-67-3

Basic information

• Product Name: N'-(4-NITRO-PHENYL)-HYDRAZINECARBOXYLIC ACID TERT-BUTYL ESTER
• Synonyms: N'-(4-NITRO-PHENYL)-HYDRAZINECARBOXYLIC ACID TERT-BUTYL ESTER;O-TERT-BUTYL-N-4-NITROPHENYL CARBAZATE;tert-butyl N-(4-nitroanilino)carbamate;TERT-BUTYL 2-(4-NITROPHENYL)HYDRAZINECARBOXYLATE
• CAS NO: 92491-67-3
• Molecular Formula: C₁₁H₁₅N₃O₄
• Molecular Weight: 253.25
• Mol File: 92491-67-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.271g/cm³
• Refractive Index: 1.58
• CAS DataBase Reference: N'-(4-NITRO-PHENYL)-HYDRAZINECARBOXYLIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: N'-(4-NITRO-PHENYL)-HYDRAZINECARBOXYLIC ACID TERT-BUTYL ESTER(92491-67-3)
• EPA Substance Registry System: N'-(4-NITRO-PHENYL)-HYDRAZINECARBOXYLIC ACID TERT-BUTYL ESTER(92491-67-3)

Safety Data

• Hazardous Substances Data: 92491-67-3(Hazardous Substances Data)

Usage

General Description

N'-(4-NITRO-PHENYL)-HYDRAZINECARBOXYLIC ACID TERT-BUTYL ESTER is a chemical compound with the molecular formula C13H15N3O5. It is a tert-butyl ester derivative of N'-carboxyphenylhydrazine, with a nitro group attached to the phenyl ring. N'-(4-NITRO-PHENYL)-HYDRAZINECARBOXYLIC ACID TERT-BUTYL ESTER is used in organic synthesis and pharmaceutical research, and it may have potential applications in the development of new drugs and agrochemicals. However, it is important to handle this chemical with care, as it may be hazardous if not handled properly.

InChI:InChI=1/C11H15N3O4/c1-11(2,3)18-10(15)13-12-8-4-6-9(7-5-8)14(16)17/h4-7,12H,1-3H3,(H,13,15)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 636-99-7 4-nitrophenylhydrazine hydrochloride 
• 105838-14-0 tert-butyl N-tosyloxycarbamate 
• 100-01-6 4-nitro-aniline 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 92722-14-0 tert-butyl 2-(4-nitrophenyl)diazenecarboxylate 
• 100-16-3 4-nitrophenylhydrazone 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 

Downstream Products

• 1694-20-8 trans-4-nitrostilbene 
• 787-64-4 2-(4-nitrophenyl)-1-benzofurane 
• 1262991-69-4 tert-butyl 2-(4-(4’-fluorophenoxy)phenyl)azocarboxylate 
• 586-78-7 para-nitrophenyl bromide 
• 13677-42-4 4-bromo-N-(4-methoxyphenyl)aniline 
• 2765-22-2 2'.5'-Dichlor-4-nitro-biphenyl 
• 17849-31-9 2-chloro-3-(4-nitrophenyl)propionitrile 
• 5332-96-7 1-(4-nitrophenyl)propan-2-one 
• 92-93-3 1-phenyl-4-nitrobenzene 
• 13444-01-4 methyl 2-(4-nitrophenyl)azocarboxylate 
• 1354828-51-5 tert-butyl 2-(4-(4-(2-(ethylamino)ethyl)phenoxy)phenyl)azocarboxylate 
• 1354828-75-3 tert-butyl 2-(4-(4-fluorophenoxy)phenyl)azoxycarboxylate 
• 1354828-74-2 4'-nitro-2-phenoxy-1,1'-biphenyl 
• 128924-06-1 4'-phenoxy-4-nitrobiphenyl 

Relevant articles and documents

Hydrogen peroxide based oxidation of hydrazines using HBr catalyst

Azo compounds (RN = NR′) are an important class of organic molecules that find wide application in organic synthesis. Herein, we report an efficient, practical and metal-free oxidation of hydrazines (RNH-NHR’) to azo compounds using 5 mol% HBr and hydrogen peroxide as terminal oxidant. This new method has been demonstrated by 40 examples with excellent yields. In addition, we showcased two examples of the one-pot sequential reactions involving our hydrazine oxidation/hydrolysis/Heck reaction or Cu-catalyzed N-arylation with aryl boronic acid. The distinct advantages of this protocol include metal-free catalysis, waste prevention, and easy operation.

Aerobic Oxidation of Alkyl 2-Phenylhydrazinecarboxylates Catalyzed by CuCl and DMAP

Recently, various fruitful organic reactions such as a catalytic Mitsunobu reaction were reported by virtue of alkyl 2-phenylazocarboxylates, however, the synthesis of alkyl 2-phenylazocarboxylates largely depended on the stoichiometric use of toxic oxidants. In this manuscript, an environment-friendly aerobic oxidative transformation of alkyl 2-phenylhydrazinecarboxylates to alkyl 2-phenylazocarboxylates is disclosed. The use of CuCl and DMAP system efficiently catalyzed the aerobic oxidation of alkyl 2-phenylhydrazinecarboxylates under mild conditions. The reaction rate of the present Cu-catalysis was much faster than that of the previously reported Fe-catalysis, and a variety of azo products were synthesized within 3 h. The present protocol was effective on larger scale. It was observed that the produced azo compound could undergo various reactions without isolation through one-pot sequential protocols.

Nucleophilic substitutions and radical reactions of phenylazocarboxylates

tert-Butyl phenylazocarboxylates are versatile building blocks for synthetic organic chemistry. Nucleophilic substitutions of the benzene ring proceed with aromatic amines and alcohols under mild conditions. The attack of aliphatic amines may be directed to the aromatic core as well as to the carbonyl unit leading to azocarboxamides. The benzene ring can further be modified through radical reactions, in which the tert-butyloxycarbonylazo group enables the generation of aryl radicals at either elevated temperatures or under acidic conditions. Radical reactions include oxygenation, halogenation, carbohalogenation, carbohydroxylation, and aryl-aryl coupling.