Irloxacin

Base Information

• Chemical Name: Irloxacin
• CAS No.: 91524-15-1
• Molecular Formula: C₁₆H₁₃FN₂O₃
• Molecular Weight: 300.289
• NSC Number: 610496
• UNII: 36SG77D21B
• DSSTox Substance ID: DTXSID10238610
• Nikkaji Number: J33.148A
• Wikidata: Q27256595
• NCI Thesaurus Code: C65961
• ChEMBL ID: CHEMBL68262
• Mol file: 91524-15-1.mol

Synonyms:1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1H-pyrrol-1-yl)quinoline-3-carboxylic acid;E 3432;E-3432;irloxacin;pirfloxacin

Chemical Property of Irloxacin

Chemical Property:

• Vapor Pressure: 1.18E-10mmHg at 25°C
• Boiling Point: 495.9°Cat760mmHg
• Flash Point: 253.7°C
• PSA: 64.23000
• Density: 1.36g/cm³
• LogP: 2.64940
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 300.09102044
• Heavy Atom Count: 22
• Complexity: 502

Purity/Quality:

95-99% ^*data from raw suppliers

IRLOXACIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Low toxicity by ingestion.
• Hazard Codes: Low toxicity by ingestion.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1C=C(C(=O)C2=CC(=C(C=C21)N3C=CC=C3)F)C(=O)O

Technology Process of Irloxacin

There total 16 articles about Irloxacin 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: 73.3%

ethyl 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1H-pyrrol-1-yl)quinoline-3-carboxylic acid (96623-79-9) → Irloxacin (91524-15-1)

Guidance literature:

With sodium hydroxide; In ethanol; water; for 1h; Heating;

Reference yield: 67.7%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 6-fluoro-7-amino-1-ethyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (75001-63-7) → Irloxacin (91524-15-1)

Guidance literature:

at 180 ℃; for 0.666667h;

DOI:10.1021/jm00395a001

Reference yield:

dimethoxytetrahydrofuran (73510-05-1) + 6-fluoro-7-amino-1-ethyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (75001-63-7) → Irloxacin (91524-15-1)

Guidance literature:

In acetic acid;

upstream raw materials:

cis,trans-2,5-dimethoxytetrahydrofuran

6-fluoro-7-amino-1-ethyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

ethyl 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1H-pyrrol-1-yl)quinoline-3-carboxylic acid

N-(2-fluoro-5-nitrophenyl)acetamide

Refernces

• 1、 Uno, Toshio,Takamatsu, Masanori,Inoue, Yoshimasa,Kawahata, Yoshihiro,Iuchi, Koji,Tsukamoto, Goro. "Synthesis of Antimicrobial Agents. 1. Syntheses and Antibacterial Activities of 7-(Azole substituted)quinolones". . p. 2163 - 2169. Retrieved 2007/10/02.
• 2、 Stefancich,Artico,Corelli,Massa,Panico,Simonetti. "1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1H-pyrrol-1-yl)-quinoline-3-carboxylic acid, a new fluorinated compound of oxacin family with high broad-spectrum antibacterial activities". . p. 237 - 248. Retrieved 2007/10/02.