23197-23-1

Basic information

• Product Name: 4-hydrazinylphenol
• Synonyms: 4-hydrazinylphenol
• CAS NO: 23197-23-1
• Molecular Formula: C₆H₈N₂O
• Molecular Weight: 124.14052
• Mol File: 23197-23-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-hydrazinylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydrazinylphenol(23197-23-1)
• EPA Substance Registry System: 4-hydrazinylphenol(23197-23-1)

Safety Data

• Hazardous Substances Data: 23197-23-1(Hazardous Substances Data)

Usage

Description

4-Hydroxyphenylhydrazine, also known as 4-hydrazinylphenol, is an organic compound with the molecular formula C6H8N2O. It is a derivative of phenol, featuring a hydroxyl group and a hydrazine group attached to the benzene ring. 4-hydrazinylphenol is known for its reactivity and is commonly used as a synthetic intermediate in the pharmaceutical and chemical industries.

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

• 106-41-2 4-bromo-phenol 
• 123-30-8 4-amino-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 
• 780806-23-7 2-(4-hydroxy-phenyl)-5-methyl-1,2-dihydro-pyrazol-3-one 
• 73264-04-7 4'-Hydroxy-antipyrine 
• 340811-91-8 8-trifluoromethoxy-2-(4-hydroxy-3-nitrophenyl)pyrazolo[4,3-c]quinolin-3(5H)-one 
• 101496-46-2 2-(4-isobutoxy-phenyl)-1,5-dimethyl-1,2-dihydro-pyrazol-3-one 
• 53157-46-3 N,N-phthalimido-2-(5-hydroxy-1H-indole-3-yl)ethylamine 
• 1416983-51-1 C₁₃H₁₄N₂O₃S 
• 92-69-3 4-Phenylphenol 

Relevant articles and documents

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

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.

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.