92491-67-3

Usage

Uses

Used in Organic Synthesis:
N'-(4-NITRO-PHENYL)-HYDRAZINECARBOXYLIC ACID TERT-BUTYL ESTER is used as a key intermediate in organic synthesis for the preparation of various complex organic molecules. Its unique structure allows for versatile chemical reactions, facilitating the synthesis of a wide range of compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, N'-(4-NITRO-PHENYL)-HYDRAZINECARBOXYLIC ACID TERT-BUTYL ESTER is utilized as a starting material or building block in the development of new drugs. Its chemical properties make it a valuable component in the design and synthesis of pharmaceutical agents with potential therapeutic applications.
Used in Agrochemical Development:
N'-(4-NITRO-PHENYL)-HYDRAZINECARBOXYLIC ACID TERT-BUTYL ESTER may also find applications in the agrochemical sector, where it can be used as a precursor in the synthesis of novel agrochemicals. Its potential use in this industry highlights its versatility and the broad scope of its applications.

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

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 100-16-3 4-nitrophenylhydrazone 
• 92722-14-0 tert-butyl 2-(4-nitrophenyl)diazenecarboxylate 
• 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 

Downstream Products

• 92722-14-0 tert-butyl 2-(4-nitrophenyl)diazenecarboxylate 
• 636-98-6 p-nitrobenzene iodide 
• 1262991-69-4 tert-butyl 2-(4-(4’-fluorophenoxy)phenyl)azocarboxylate 
• 1262991-74-1 methyl (S)-2-amino-3-[4-(4-tert-butyl-azocarboxylatephenoxy)phenyl]propionate 
• 1262991-78-5 C₂₈H₃₁N₃O₅ 
• 1262991-80-9 C₂₉H₃₆N₂O₄ 
• 1262991-88-7 4-(tert-butyloxycarbonylazophenyl)-(4-methoxyphenyl)amine 
• 1262991-89-8 4-(tert-butyloxycarbonylazophenyl)-(4-chlorophenyl)amine 
• 886762-45-4 1-fluoro-4-(4-iodophenoxy)benzene 
• 1262991-93-4 3-phenylmorphine 
• 100-02-7 4-nitro-phenol 
• 1354828-53-7 tert-butyl 2-(4-sec-butylaminophenyl)azocarboxylate 
• 1354828-59-3 N-butyl 2-(4-nitrophenyl)azocarboxamide 
• 1354828-60-6 N-butyl 2-(4-(4-fluorophenoxy)phenyl)azocarboxamide 

Relevant academic research and scientific papers

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.

Selective Functionalization of Graphene at Defect-Activated Sites by Arylazocarboxylic tert-Butyl Esters

The development of versatile functionalization concepts for graphene is currently in the focus of research. Upon oxo-functionalization of graphite, the full surface of graphene becomes accessible for C?C bond formation to introduce out-of-plane functional

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.

Palladium/copper-catalyzed arylation of alkenes with N′-acyl arylhydrazines

A novel ligand-free palladium/copper-catalyzed Heck-type coupling reaction of alkenes and N′-acyl arylhydrazines has been developed by using air as the terminal oxidant. This protocol features wide functional group tolerance and produces highly chemoselective and regioselective products with good to excellent yields.

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.

N-Boc-O-tosyl hydroxylamine as a safe and efficient nitrogen source for the N-amination of aryl and alkyl amines: Electrophylic amination

β-Boc-protected aryl and alkyl hydrazines, useful intermediates for azapeptides and N-substituted pyrazoles, were synthesized by electrophylic amination methodology, using less energetic N-Boc-O-tosyl hydroxylamine as an efficient nitrogen source. Also we have demonstrated a two-step, chromatography-free synthesis of N-Boc-O-tosyl hydroxylamine. Georg Thieme Verlag Stuttgart - New York.

4-substituted tert-butyl phenylazocarboxylates-synthetic equivalents for the para-phenyl radical cation

First electrophile, then radical: 4-Substituted tert-butyl phenylazocarboxylates 1 are versatile synthetic equivalents of the para-phenyl radical cation 2. The tert-butyloxycarbonylazo group enables nucleophilic substitutions to proceed under mild conditions and can later be employed for the generation of aryl radicals. Copyright

Addition of arylboronic acids to symmetrical and unsymmetrical azo compounds

(Chemical Equation Presented) The addition of aryl- and heteroarylboronic acids to azo compounds is described. Copper salt catalysis was necessary to perform the reaction under mild conditions and high yields. Excellent regioselectivity was observed in addition to unsymmetrical azo compounds.