5351-17-7

Basic information

• Product Name: 4-Aminobenzohydrazide
• Synonyms: 4-amino-benzoicacihydrazide;4-Aminobenzoylhydrazine;Amben hydrazide;ambenhydrazide;aminostimil;Benzoic acid, p-amino-, hydrazide;p-Amino benzoyl hydrazine;p-Aminobenzoic hydrazide
• CAS NO: 5351-17-7
• Molecular Formula: C₇H₉N₃O
• Molecular Weight: 151.17
• EINECS: 226-324-4
• Product Categories: Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes;Amines;Carbonyl Compounds;Hydrazides;Organic Building Blocks
• Mol File: 5351-17-7.mol
• Article Data: 79

Chemical Properties

• Melting Point: 225-227 °C(lit.)
• Boiling Point: 273.17°C (rough estimate)
• Flash Point: °C
• Appearance: White or beige/Crystals or Powder
• Density: 1.2100 (rough estimate)
• Refractive Index: 1.5860 (estimate)
• Storage Temp.: -20C
• PKA: 13.05±0.10(Predicted)
• Water Solubility: Soluble in DMSO (10 mg/ml), dilute acids, and water (partly miscible).
• BRN: 639053
• CAS DataBase Reference: 4-Aminobenzohydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Aminobenzohydrazide(5351-17-7)
• EPA Substance Registry System: 4-Aminobenzohydrazide(5351-17-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: DG2580000
• HazardClass: IRRITANT
• Hazardous Substances Data: 5351-17-7(Hazardous Substances Data)

Usage

Description

4-Aminobenzoic acid hydrazide (4-ABAH) is a white or beige crystalline compound with significant biological and chemical properties. It acts as an irreversible inhibitor of myeloperoxidase (MPO), a key enzyme involved in the immune response and various pathological conditions. With its ability to reduce the production of hypochlorous acid (HOCl) and inhibit the formation of neutrophil extracellular traps (NETs), 4-ABAH has demonstrated potential therapeutic effects in conditions like cerebral ischemia.

Uses

Used in Pharmaceutical Industry:
4-Aminobenzohydrazide is used as a pharmaceutical compound for its role in inhibiting myeloperoxidase (MPO), which can help reduce the severity of neurological deficits and infarct volume in a mouse model of cerebral ischemia induced by transient middle cerebral artery occlusion (MCAO).
Used in Enzyme Preparations:
In the field of biochemistry, 4-Aminobenzohydrazide is used as a reactant in enzyme preparations, where it can help study the peroxidation activity of MPO and its effects on various biological processes.
Used in Cell Cultures:
4-Aminobenzohydrazide is utilized in cell cultures to investigate the effects of MPO inhibition on cellular processes, particularly in the context of immune response and inflammation.
Used in Chemical Synthesis:
4-Aminobenzohydrazide is used as a reactant to synthesize various compounds, such as Acylhydrazone Schiff base ligand by condensation reaction with 2-acetylpyridine, oligomeric transition metal complexes for organic-inorganic hybrid devices with efficient electrical and photoelectrical properties, and oxovanadium(IV)-hydrazide complex as a potential radical scavenger.
These applications highlight the versatility of 4-Aminobenzohydrazide in different industries, from pharmaceuticals to materials science, where it contributes to the development of novel therapeutics, enzyme studies, and advanced materials with improved properties.

InChI:InChI=1/C7H9N3O/c8-6-3-1-5(2-4-6)7(11)10-9/h1-4H,8-9H2,(H,10,11)

Upstream product

• 636-97-5 N-amino-(4-nitrophenyl)carboxamide 
• 64-17-5 ethanol 
• 555-16-8 4-nitrobenzaldehdye 
• 79785-97-0 hydrazine hydrate 
• 94-09-7 p-aminoethylbenzoate 
• 150-13-0 4-amino-benzoic acid 
• 62-23-7 4-nitro-benzoic acid 
• 16106-38-0 4-aminobenzoyl chloride 
• 4005-02-1 ethyl 4-(2-methyl-4-oxoquinazolin-3(4H)-yl)benzoate 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 10073-94-6 4-(2-methyl-4-oxoquinazoline-3-yl)benzoic acid hydrazide 
• 110925-32-1 4-Amino-benzoic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride 
• 99-77-4 ethyl 4-nitrobenzoate 
• 619-45-4 4-methoxycarbonyl aniline 

Downstream Products

• 105402-22-0 5-hydroxymethyl-furan-2-carbaldehyd-(4-amino-benzoylhydrazone) 
• 35219-13-7 4-(1,3,4-oxadiazol-2-yl)aniline 
• 109403-79-4 N²,N⁴-bis-(4-amino-benzoyl)-formohydrazidine 
• 88844-07-9 4-(5,6-diphenyl-[1,2,4]triazin-3-yl)-aniline 
• 97742-08-0 4-amino-benzoic acid-(4-nitro-benzylidenehydrazide) 
• 22443-81-8 <2,5-Methylen-1,2,5,6-tetrahydro-benzaldehyd>-p-amino-benzoylhydrazon 
• 62830-46-0 4-Amino-benzoic acid [2-hydroxy-3-methyl-4-oxo-4H-naphthalen-(1Z)-ylidene]-hydrazide 
• 62830-51-7 4-Amino-benzoic acid [3-methyl-4-oxo-4H-naphthalen-(1E)-ylidene]-hydrazide 
• 22518-82-7 <2,5-Methylen-hexahydro-benzaldehyd>-p-amino-benzoylhydrazon 
• 556-18-3 4-aminobenzaldehyde 
• 127786-25-8 C₂₈H₂₁N₇O₄ 
• 127786-19-0 C₃₀H₂₃N₇O₃ 
• 127786-23-6 C₃₀H₂₃N₇O₃ 
• 127786-20-3 C₂₈H₂₁N₇O₃ 

Relevant articles and documents

Crystal and molecular structure of 4-aminobenzohydrazide

The molecule of 4-aminobenzohydrazide is essentially planar and geometric parameters conform to literature precedents. Supramolecular N- H???O and N-H???N interactions combine to link molecules of 4-aminobenzohydrazide into a three-dimensional network. Weaker N-H???N and N-H???π interactions consolidate the structure. The compound crystallizes in the monoclinic space group P2 1/n with a = 5.411(2) A, b = 14.000(6) A, c = 9.894(4) A, β = 103.917(7)°, and Z = 4.

Design, synthesis, in vitro and in vivo evaluation against MRSA and molecular docking studies of novel pleuromutilin derivatives bearing 1, 3, 4-oxadiazole linker

A class of pleuromutilin derivatives containing 1, 3, 4-oxadiazole were designed and synthesized as potential antibacterial agents against Methicillin-resistant staphylococcus aureus (MRSA). The ultrasound-assisted reaction was proposed as a green chemistry method to synthesize 1, 3, 4-oxadiazole derivatives (intermediates 85–110). Among these pleuromutilin derivatives, compound 133 was found to be the strongest antibacterial derivative against MRSA (MIC = 0.125 μg/mL). Furthermore, the result of the time-kill curves displayed that compound 133 could inhibit the growth of MRSA in vitro quickly (- 4.36 log10 CFU/mL reduction). Then, compound 133 (- 1.82 log10 CFU/mL) displayed superior in vivo antibacterial efficacy than tiamulin (- 0.82 log10 CFU/mL) in reducing MRSA load in mice thigh model. Besides, compound 133 exhibited low cytotoxicity to RAW 264.7 cells. Molecular docking studies revealed that compound 133 was successfully localized in the binding pocket of 50S ribosomal subunit (ΔGb = -10.50 kcal/mol). The results indicated that these pleuromutilin derivatives containing 1, 3, 4-oxadiazole might be further developed into novel antibiotics against MRSA.

Aqueous Zn2+ analysis: Specific recognition and instant imaging by Schiff base fluorescent probes

Two Schiff base fluorescence probes for aqueous Zn2+ were synthesized by introducing salicylaldehyde benzoyl hydrazine as the recognition group and C=N as the characteristic fluorescence chromophore. Spectroscopic analyses, mainly FS, illuminated the probes’ highly specific recognition towards Zn2+ over other metal ions, accompanied by steady optical properties at a wide pH range of 6.0 to 9.0. Moreover, cytotoxicity and fluorescence imaging in living ECV304 cells identified the probes’ instant response and membrane permeability. These results predicted the probes’ future applications for instant Zn2+ detection in a clinical diagnosis and dynamic analysis of Zn2+ in biological systems.