Difloxacin

Base Information

• Chemical Name: Difloxacin
• CAS No.: 98106-17-3
• Molecular Formula: C21H19F2N3O3
• Molecular Weight: 399.397
• Hs Code.: 2933990090
• UNII: 5Z7OO9FNFD
• DSSTox Substance ID: DTXSID5048348
• Nikkaji Number: J22.039F
• Wikipedia: Difloxacin
• Wikidata: Q5275450
• NCI Thesaurus Code: C65382
• Metabolomics Workbench ID: 67777
• ChEMBL ID: CHEMBL6259
• Mol file: 98106-17-3.mol

Synonyms:1-(4-fluorophenyl)-6-fluoro-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid;1-FFMPOC;6-fluoro-1-(4-fluorophenyl)-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-quinolone-3-carboxylic acid;A 56619;A-56619;Dicural;difloxacin;difloxacin hydrochloride

Chemical Property of Difloxacin

Chemical Property:

• Appearance/Colour: whtie-cream to yellowish crystalline powder
• Melting Point: 279-282 °C(Solv: chloroform (67-66-3); ethanol (64-17-5))
• Boiling Point: 595.5 °C at 760 mmHg
• PKA: 6.17±0.41(Predicted)
• Flash Point: 313.9 °C
• PSA: 65.78000
• Density: 1.409 g/cm³
• LogP: 2.72180
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 399.13944780
• Heavy Atom Count: 29
• Complexity: 672

Purity/Quality:

Difloxacin hydrochloride salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCN(CC1)C2=C(C=C3C(=C2)N(C=C(C3=O)C(=O)O)C4=CC=C(C=C4)F)F
• Description: Difloxacin (INN) is a second-generation, synthetic fluoroquinolone antibiotic used in veterinary medicine,it has broad-spectrum, concentration dependent, bactericidal activity; however, its efficacy is not as good as enrofloxacin or pradofloxacin.
• Physical properties: Whtie-Cream to Yellowish Crystalline Powder
• Uses: Difloxacin is a fluoroquinolone antibacterial structurally related to norfloxacin.

Technology Process of Difloxacin

There total 15 articles about Difloxacin 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: 94.0%

→ difloxacin (98106-17-3)

Guidance literature:

at 130 ℃; for 24h;

In acetonitrile; for 3h; Reflux;

With sodium hydroxide; In acetonitrile; at 100 ℃; for 4h;

Reference yield:

2,4-dichloro-5-fluoroacetophenone (704-10-9) → difloxacin (98106-17-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / NaH / 1.5 h / 80 °C

2: Ac₂O / 2 h / 130 °C

3: CH₂Cl₂ / 0.5 h / Ambient temperature

4: NaH / 1,2-dimethoxy-ethane / 3 h / 80 °C

5: aq. NaOH / tetrahydrofuran / 1.5 h / 80 °C

6: 21.3 g / various solvent(s) / 24 h / 110 °C

With sodium hydroxide; acetic anhydride; sodium hydride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1021/jm00149a003

Reference yield:

ethyl 2,4-dichloro-5-fluoro-benzoyl-acetate (86483-51-4) → difloxacin (98106-17-3)

Guidance literature:

Multi-step reaction with 5 steps

1: Ac₂O / 2 h / 130 °C

2: CH₂Cl₂ / 0.5 h / Ambient temperature

3: NaH / 1,2-dimethoxy-ethane / 3 h / 80 °C

4: aq. NaOH / tetrahydrofuran / 1.5 h / 80 °C

5: 21.3 g / various solvent(s) / 24 h / 110 °C

With sodium hydroxide; acetic anhydride; sodium hydride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1021/jm00149a003

upstream raw materials:

1-methyl-piperazine

7-Chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

ethyl 2,4,5-trifluorobenzoylacetate

N,N-dimethyl-formamide dimethyl acetal

Refernces

• 1、 -. "NOVEL METHOD OF SYNTHESIS OF FLUOROQUINOLONES". Page/Page column 6; 9. . Retrieved 2009/04/24.
• 2、 Hermecz, Istvan,Vasvari-Debreczy, Lelle,Podanyi, Benjamin,Kereszturi, Geza,Balogh, Maria,Horvath, Agnes,Varkonyi, Peter. "Regioselective nucleophilic substitution of halogen derivatives of 1-substituted 4-oxo-1,4-dihydroquinoline-3-carboxylic acids". . p. 1111 - 1116. Retrieved 2007/10/03.