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% min ^*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
• Description: 4-Aminobenzoic acid hydrazide (4-ABAH) is an irreversible inhibitor of myeloperoxidase (MPO; IC50 = 0.3 μM). It reduces the production of hypochlorous acid (HOCl) induced by opsonized zymosan or phorbol 12-myristate 13-acetate (PMA; ) in isolated human neutrophils with IC50 values of 16 and 2.2 μM, respectively. 4-ABAH inhibits PMA-induced formation of neutrophil extracellular traps (NETs) in the same cells. It reduces infarct volume and the severity of neurological deficits, as well as increases survival, in a mouse model of cerebral ischemia induced by transient middle cerebral artery occlusion (MCAO) when administered at a dose of 40 mg/kg twice per day.
• Uses: 4-Aminobenzhydrazide has an important role in the peroxidation activity of MPO. It is also used in enzyme preparations and in cell cultures. 4-Aminobenzoic hydrazide can be used as a reactant to synthesize:Acylhydrazone Schiff base ligand by condensation reaction with 2-acetylpyridine. Oligomeric transition metal complexes applicable in the fabrication of organic-inorganic hybrid devices with efficient electrical and photoelectrical properties. Oxovanadium(IV)-hydrazide complex as a potential radical scavenger.

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:

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}

4-(4-ethoxy-phenyl)-1-(4-amino-benzoyl)-thiosemicarbazide

Refernces

• 1、 Arafa, Reem K.,El-Zahabi, Heba S. A.,Hassan, Heba,Mousa, Safya M.,Nossier, Eman S.,Shalaby, AL Shimaa G.. "Antibacterial and anticancer profiling of new benzocaine derivatives: Design, synthesis, and molecular mechanism of action". . . Retrieved 2022/02/07.
• 2、 Bai, Hangyu,Jiang, Weiqi,Li, Qi,Li, Tian,Ma, Shichuang,Shi, Baojun,Wu, Wenjun. "Design, Synthesis, and Study of the Insecticidal Activity of Novel Steroidal 1,3,4-Oxadiazoles". . p. 11572 - 11581. Retrieved 2021/10/12.