7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase ID: 53631
• Molecular Formular: C13H9ClFNO3
• Molecular Mass: 281.6668632
• Monoisotopic Mass: 281.02549905
• SMILES: c1(c(=O)c2c(n(c1)C1CC1)cc(c(c2)F)Cl)C(=O)O
• Canonical SMILES: OC(=O)c1cn(C2CC2)c2c(c1=O)cc(c(c2)Cl)F
• InChI: InChI=1S/C13H9ClFNO3/c14-9-4-11-7(3-10(9)15)12(17)8(13(18)19)5-16(11)6-1-2-6/h3-6H,1-2H2,(H,18,19)
• InChIKey: ISPVACVJFUIDPD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: 7-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
• Synonyms: 1-Cyclopropyl-1,4-dihydro-4-oxo-6-fluoro-7-chloro-3-quinolinecarboxylic Acid; 7-Chloro-1-cyclopropyl-6-fluoro-3-carboxy-1,4-dihydro-4-oxoquinoline; 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic Acid; 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid; 7-Chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid; 7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid; 7-Chloro-1-cyclopropyl-1,4-dihydro-6-fluoroquinol-4-one-3-carboxylic acid; Ciprofloxacin Related Compound A (USP); Ciprofloxacin impurity A (PhEur); 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid; Fluoroquinolonic acid; Fluoroquinolonic acid; Q-Acid; 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid; 7-氯-6-氟-1-环丙基-1,4-二氢-4-氧-3-喹啉羧酸; 氟喹诺酮酸; Q-酸; 氟喹诺酮酸; 7-氯-6-氟-1-环丙基-1,4-二氢-4-氧-3-喹啉羧酸

Database IDs

• CAS Number: 86393-33-1
• EC Number: 405-050-0
• MDL Number: MFCD00792458
• PubChem SID: 24877846; 162058394
• PubChem CID: 483180

CALCULATED PROPERTIES

• Acid pKa: 5.686229
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.3676782
• LogD (pH = 7.4): 0.86991966
• Log P: 2.5854166
• Molar Refractivity: 67.5602 cm^3
• Polarizability: 24.968056 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Light Yellow Solid
• Melting Point: 240-242°C; 242-245 °C(lit.); 242-245°C; 244 - 245°C
• Hydrophobicity(logP): 2.781

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Harmful; IRRITANT
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 22-52/53
• Safety Statements: 22-61
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H412
• GHS Precautionary statements: P273
• Storage Temperature: room temp

Product Information

• Purity: 95%; 95+%; 96%
• Grade: certified reference material
• Packaging: pkg of 500 mg
• Pharmacopeia Traceability: traceable to USP 1278302
• Empirical Formula (Hill Notation): C13H9ClFNO3

DETAILS

Sigma Aldrich - 531901

Packaging
25 g in glass bottle

Sigma Aldrich - PHR1174

General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.

Toronto Research Chemicals - C365135

A metabolite of Ciprofloxacin, a fluorinated quinolone antibacterial.

REFERENCES

• Siefert, H.M., et al.: Arzneim.-Forsch., 36, 1496 (1986)
• Zhi, C., J. Med. Chem., 49, 1455 (1986)
• Trefi, S., et al.: J. Pharm. Biomed. Anal., 44, 743 (1986)