Piretanide

Base Information

• Chemical Name: Piretanide
• CAS No.: 55837-27-9
• Molecular Formula: C17H18N2O5S
• Molecular Weight: 362.406
• Hs Code.: 2935009090
• European Community (EC) Number: 259-852-9
• UNII: DQ6KK6GV93
• DSSTox Substance ID: DTXSID2023488
• Nikkaji Number: J3.520C
• Wikipedia: Piretanide
• Wikidata: Q3905617
• NCI Thesaurus Code: C66419
• Pharos Ligand ID: NU8D1QVCGWGS
• Metabolomics Workbench ID: 147474
• ChEMBL ID: CHEMBL349803
• Mol file: 55837-27-9.mol

Synonyms:4-phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid;HOE 118;piretanide

Chemical Property of Piretanide

Chemical Property:

• Appearance/Colour: Pale yellow powder.
• Vapor Pressure: 3.92E-15mmHg at 25°C
• Melting Point: 225-227°
• Refractive Index: 1.64
• Boiling Point: 597.676 °C at 760 mmHg
• PKA: 10.22±0.60(Predicted)
• Flash Point: 315.263 °C
• PSA: 118.31000
• Density: 1.415 g/cm³
• LogP: 4.27080
• Storage Temp.: 2-8°C
• Solubility.: Very slightly soluble in water, sparingly soluble in anhydrous ethanol. It shows polymorphism (5.9).
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 362.09364285
• Heavy Atom Count: 25
• Complexity: 564

Purity/Quality:

99% ^*data from raw suppliers

Piretanide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(C1)C2=C(C(=CC(=C2)C(=O)O)S(=O)(=O)N)OC3=CC=CC=C3
• Uses: High-ceiling loop diuretic; structurally related to Bumetanide (B689550). Diuretic.
• Therapeutic Function: Diuretic

Technology Process of Piretanide

There total 5 articles about Piretanide 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:

1,4-dibromo-butane (110-52-1) + 3-amino-4-phenoxy-5-sulphamoylbenzoic acid methyl ester (56106-57-1) → piretanide (55837-27-9)

Guidance literature:

With sodium iodide; In N,N-dimethyl-formamide; acetone;

Reference yield:

1,4-dibromo-butane (110-52-1) + 5-amino-3-(dimethylaminomethylenesulfamoyl)-4-phenoxybenzoic acid methyl ester (60376-74-1) → piretanide (55837-27-9)

Guidance literature:

In N-methyl-acetamide;

Reference yield:

→ piretanide (55837-27-9)

Guidance literature:

upstream raw materials:

1,4-dibromo-butane

3-amino-4-phenoxy-5-sulphamoylbenzoic acid methyl ester

5-amino-3-(dimethylaminomethylenesulfamoyl)-4-phenoxybenzoic acid methyl ester

Downstream raw materials:

3-(1-Pyrrolidinyl)-4-phenoxy-5-sulphamyl-benzoic acid methyl ester

4-phenoxy-3-(1-pyrrolidinyl)-5-dimethylsulphamoylbenzoic acid

Refernces

• 1、 -. "Novel 4-phenoxy-5-sulfamylbenzoic acid derivatives". . . Retrieved 2008/06/13.