CAS 5351-17-7 4-Aminobenzoic acid hydrazide (HCID 21450)

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Basic information

CAS: 5351-17-7
Standard SMILES: NNC(=O)c1ccc(N)cc1
InChIKey: WPBZMCGPFHZRHJ-UHFFFAOYSA-N
Molecular formula: C7H9N3O
Average molar mass: 151.17 g/mol
Monoisotopic mass: 151.07456191

Overview

4-aminobenzohydrazide is an aminobenzoic acid. It has a role as an EC 1.11.2.2 (myeloperoxidase) inhibitor.

Names & identifiers

Preferred name: 4-Aminobenzoic acid hydrazide
IUPAC: 4-aminobenzohydrazide
English name: 4-Aminobenzohydrazide
Molecular formula: C7H9N3O
Molecular weight: 151.17

Names & synonyms

5351-17-74-Aminobenzhydrazide4-Aminobenzoic acid hydrazideAminostimilp-Aminobenzoic acid hydrazidepara-AminobenzhydrazideDTXSID302017204-aminobenzoic acid-hydrazideRefChem:97833DTXCID60124211226-324-44-Aminobenzohydrazide

Show more names

4-POBN4NPhCON2WLN: ZNUYQR DZambenhydrazideTIMTEC-BB SBB007555N,4-Diaminobenzamide

Amben hydrazidep-Aminobenzhydrazide4-Aminobenzoylhydrazinep-Aminobenzoyl hydrazideBenzoic acid, 4-amino-, hydrazidep-Aminobenzoic hydrazidep-Aminobenzoylhydrazine4-Aminobenzoic hydrazide

Database identifiers

CAS: 5351-17-7
PubChem CID: 21450
DTXSID: DTXSID30201720
ChEMBL: CHEMBL2170241
ChEBI: CHEBI:233355
EC Number: 226-324-4

Properties

Computed structural properties

XLogP: -0.7
Topological polar surface area: 81.1 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 3
Rotatable bonds: 1
Heavy atoms: 11
Formal charge: 0
Complexity: 141

Experimental & physicochemical properties

LogP-0.75

Physicochemical properties

Melting point: 225 · 225-227 °C (lit.)
Boiling point: 273.17 °C · 273.17°C (rough estimate)
Density: 1.21 · 1.2100 (rough estimate)
refractive index: 1.586 · 1.5860 (estimate)
storage temp.: Keep in dark place,Inert atmosphere,Room temperature
solubility: 10 mg/ml; · DMF: 10 mg/ml; DMSO: 14 mg/ml; DMSO:PBS(pH7.2) (1:1): 0.5 mg/ml
pka: 13.05 · 13.05±0.10(Predicted)
form: Crystals or Powder
color: White or beige
Water Solubility: Soluble in DMSO (10 mg/ml), dilute acids, and water (partly miscible).
BRN: 639053 · 639053
InChI: 1S/C7H9N3O/c8-6-3-1-5(2-4-6)7(11)10-9/h1-4H,8-9H2,(H,10,11)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
rtecs: DG2580000
hs_code: 29280000
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
hazard_class: IRRITANT
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
Precautionary statements: P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a

Chemistry & industry

Applications · 3 items

Description4-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.

Uses4-Aminobenzhydrazide has an important role in the peroxidation activity of MPO. It is also used in enzyme preparations and in cell cultures.

Uses4-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.