4-Aminobenzohydrazide

Base Information

• Chemical Name: 4-Aminobenzohydrazide
• CAS No.: 5351-17-7
• Molecular Formula: C7H9 N3 O
• Molecular Weight: 151.168
• Hs Code.: 29280000
• European Community (EC) Number: 226-324-4
• NSC Number: 640
• DSSTox Substance ID: DTXSID30201720
• Nikkaji Number: J20.610E
• Wikidata: Q72438042
• Pharos Ligand ID: ANY7PPV84UG4
• ChEMBL ID: CHEMBL2170241
• Mol file: 5351-17-7.mol

Synonyms:4-aminobenzhydrazide;4-aminobenzoic acid-hydrazide;aminostimil;p-aminobenzoic acid hydrazide;para-aminobenzhydrazide

Chemical Property of 4-Aminobenzohydrazide

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 224-228 ºC
• Refractive Index: 1.641
• Boiling Point: °Cat760mmHg
• PKA: 13.05±0.10(Predicted)
• Flash Point: °C
• PSA: 81.14000
• Density: 1.267 g/cm³
• LogP: 1.54470
• Storage Temp.: -20C
• Water Solubility.: Soluble in DMSO (10 mg/ml), dilute acids, and water (partly miscible).
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 151.074561919
• Heavy Atom Count: 11
• Complexity: 141

Purity/Quality:

99% ^*data from raw suppliers

4-Aminobenzhydrazide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)NN)N
• General Description: 4-Aminobenzohydrazide serves as a key precursor in the synthesis of hydrazone derivatives with demonstrated antimicrobial potential. Derived hydrazones exhibit structure-dependent bioactivity, where electron-donating substitutions enhance antibacterial effects, while electron-withdrawing groups favor antifungal properties. Notably, certain derivatives show promise as inhibitors of Mycobacterium tuberculosis InhA protein, highlighting their relevance in antitubercular drug development. The compound’s versatility in forming bioactive hydrazones underscores its utility in medicinal chemistry. (Returned paragraph focuses on the compound’s role and implications, excluding literature-specific details.)

Technology Process of 4-Aminobenzohydrazide

There total 18 articles about 4-Aminobenzohydrazide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

p-aminoethylbenzoate (94-09-7) → 4-aminobenzohydrazide (5351-17-7)

Guidance literature:

With hydrazine hydrate; In ethanol; water; Reflux;

DOI:10.1016/j.bmc.2015.06.051

Reference yield: 99.0%

4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → 4-aminobenzohydrazide (5351-17-7)

Guidance literature:

4-amino-benzoic acid; With sulfuric acid; In ethanol; for 6h; Reflux;

With hydrazine hydrate; sodium hydrogencarbonate; acetic acid; Reflux;

DOI:10.1016/j.ejmech.2017.06.036

Reference yield: 95.0%

hydrazine hydrate (79785-97-0) + p-aminoethylbenzoate (94-09-7) → 4-aminobenzohydrazide (5351-17-7)

Guidance literature:

In ethanol; for 4h; Reflux;

DOI:10.1002/ardp.202100451

upstream raw materials:

ethanol

5-hydroxymethyl-furan-2-carbaldehyd-(4-amino-benzoylhydrazone)

phenylhydrazine

p-aminoethylbenzoate

Downstream raw materials:

furfural-(4-amino-benzoylhydrazone)

4-amino-benzoic acid-(1-methyl-[4]piperidylidenehydrazide)

5-hydroxymethyl-furan-2-carbaldehyd-(4-amino-benzoylhydrazone)

4-amino-benzoic acid-{4-[bis-(2-chloro-ethyl)-amino]-benzylidenehydrazide}

Refernces

Synthesis, structure analysis, biological activity and molecular docking studies of some hydrazones derived from 4-aminobenzohydrazide

10.1016/j.molstruc.2020.129354

This research presents the synthesis, structural analysis, biological activity, and molecular docking studies of eight hydrazones derived from 4-aminobenzohydrazide. The purpose of the study was to explore the potential of these compounds as antimicrobial agents, specifically against bacteria and fungi, and to understand their molecular interactions through docking studies. The researchers synthesized (E)-4-amino-N′-(substituted benzylidene) benzohydrazides (1-8) by condensing 4-aminobenzohydrazide with appropriate aldehydes in methanol. The synthesized compounds were characterized using various spectroscopic techniques, including FT-IR, 1H, and 13C NMR. The study concluded that compounds with electron-donating groups showed good antibacterial activity, while those with electron-withdrawing groups exhibited good antifungal activities. Molecular docking studies indicated that compounds 6 and 8 had excellent glide score values, suggesting their potential as inhibitors for Mycobacterium tuberculosis InhA protein, which plays a crucial role in the biosynthesis of mycolic acids in the mycobacterial cell wall.