23197-23-1

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxyphenylhydrazine is used as a reagent for the synthesis of pyrazolone derivatives, which are known for their antibacterial properties. These derivatives are effective against a wide range of microorganisms, making them valuable in the development of new antibiotics and antimicrobial agents.
Used in Chemical Synthesis:
In the chemical industry, 4-hydrazinylphenol serves as an important intermediate for the synthesis of various organic compounds. Its unique structure allows for further functionalization and modification, leading to the creation of a diverse array of products with different applications.

Upstream product

• 123-30-8 4-amino-phenol 
• 106-41-2 4-bromo-phenol 

Downstream Products

• 207231-08-1 2-(4-Hydroxy-phenyl)-8-trifluoromethoxy-2,5-dihydro-pyrazolo[4,3-c]quinolin-3-one 
• 77779-51-2 CGS 11361 
• 54840-15-2 4-N-tert-butoxycarbonylaminophenol 
• 1416983-51-1 C₁₃H₁₄N₂O₃S 
• 780806-23-7 2-(4-hydroxy-phenyl)-5-methyl-1,2-dihydro-pyrazol-3-one 
• 340811-91-8 8-trifluoromethoxy-2-(4-hydroxy-3-nitrophenyl)pyrazolo[4,3-c]quinolin-3(5H)-one 
• 73264-04-7 4'-Hydroxy-antipyrine 

Relevant academic research and scientific papers

Synthesis of substituted 3-[(4-oxocyclohexa-2,5-dien-1-ylidene)-hydrazinylidene]-1,3-dihydro-2H-indol-2-ones and their reactions with hydrogen chloride

4-Hydroxyphenylhydrazones of isatin derivatives were synthesized and oxidized with lead compounds to the corresponding azines. The introduction of isatin fragment in a quinoid system increases the redox potential of the system compared with 1,4-benzoquino

Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine

In this work, we developed a ligand- and base-free visible-light-mediated protocol for the photoredox syntheses of arylphosphonates and, for the first time, alkyl phosphonates. Zinc phthalocyanine-photocatalyzed Csp2-P and Csp3-P bond formations were efficiently achieved by reacting aryl/alkylhydrazines with trialkylphosphites in the presence of air serving as an abundant oxidant. The reaction conditions tolerated a wide variety of functional groups.

Hydrazo coupling: The efficient transition-metal-free C-H functionalization of 8-hydroxyquinoline and phenol through base catalysis

Azodicarboxylate esters are common reagents in organic synthesis laboratories due to their utility in the Mitsunobu reaction. They can also be regarded as possible starting compounds for C-H functionalization, which up until now has been mainly achieved by transition-metal-catalyzed reactions. We have developed a novel reaction involving the quantitative coupling of 8-hydroxyquinoline or phenol with azodicarboxylate esters. The functionalization proceeds under mild base-catalyzed conditions selectively, and either the ortho-position of 8-hydroxyquinoline or para-position of the phenol/naphthol is involved in the reaction. This type of transformation can be considered as "hydrazo coupling" (by analogy with azo coupling). Herein, we discuss a plausible mechanism for this catalyzed substitution, backing up our findings with deuterium NMR experiments and by varying the starting compounds and bases. Using Boc-NN-Boc as a substrate, we have developed the convenient and efficient synthesis of (8-hydroxyquinolin-7-yl)hydrazines, as well as demonstrating a new stereoselective route for the synthesis of medicinally important 4-hydroxyphenylhydrazine for laboratory use, which almost doubles the yield of the common industrial process and reduces the number of synthetic steps. A new "one-pot" procedure for the synthesis of aromatic 8-hydroxyquinolin-7-yl hydrazones was applied.

Efficient synthesis of aryl hydrazines using copper-catalyzed cross-coupling of aryl halides with hydrazine in PEG-400

An efficient and convenient method for the synthesis of aryl hydrazines is described via copper-catalyzed cross-coupling of aryl halides with aqueous hydrazine in PEG-400. This protocol is applicable to both electron-deficient and electron-rich aryl iodides and bromides, and even to sterically hindered substrates, giving aryl hydrazines in good to excellent yields.

Carbazole methyl malonates

A process for the preparation of α-methyl-carbazole-2-acetic acids, which comprises reacting an α-methyl-3-oxocyclohexane malonic acid di-lower alkyl ester with a substituted phenylhydrazine, and thereafter sequentially oxidizing and hydrolyzing the reaction product to obtain the desired acid, is described.