(2S)-6,7-difluoro-2-methyl-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

• ChemBase ID: 151724
• Molecular Formular: C13H9F2NO4
• Molecular Mass: 281.2116664
• Monoisotopic Mass: 281.04996421
• SMILES: C[C@H]1COc2c3n1cc(c(=O)c3cc(c2F)F)C(=O)O
• Canonical SMILES: OC(=O)c1cn2[C@@H](C)COc3c2c(c1=O)cc(c3F)F
• InChI: InChI=1S/C13H9F2NO4/c1-5-4-20-12-9(15)8(14)2-6-10(12)16(5)3-7(11(6)17)13(18)19/h2-3,5H,4H2,1H3,(H,18,19)/t5-/m0/s1
• InChIKey: NVKWWNNJFKZNJO-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6,7-difluoro-2-methyl-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^5,^1^3]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
• IUPAC Traditional name: (2S)-6,7-difluoro-2-methyl-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^5,^1^3]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
• Synonyms: (3S)-9,10-Difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid; Levofloxacin Q-Acid; Levofloxacin Carboxylic Acid (Levofloxacin Difluoro Impurity); (S)-(-)-9,10-Difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido-[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid; (S)-(-)-9,10-Difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid; 左旋氧氟沙星羧酸

Database IDs

• CAS Number: 100986-89-8
• MDL Number: MFCD04039905
• PubChem SID: 24880598; 162245874
• PubChem CID: 688333

CALCULATED PROPERTIES

• Acid pKa: 5.5150814
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.4524573
• LogD (pH = 7.4): -0.13491902
• Log P: 1.7458881
• Molar Refractivity: 64.6736 cm^3
• Polarizability: 23.55114 Å^3
• Polar Surface Area: 66.84 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (sparingly)
• Apperance: White Solid
• Melting Point: >300 °C(lit.); >300°C; 301-310°C
• Optical Rotation: [α]20/D -64°, c = 1% in DMSO; -64 (c=1 in DMSO)

Safety Information

• Storage Condition: Refrigerator
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%; 97+%
• Empirical Formula (Hill Notation): C13H9F2NO4

DETAILS

Sigma Aldrich - 570877

Packaging
1, 5 g in glass bottle

Toronto Research Chemicals - L360250

Levofloxacin intermediate.

REFERENCES

• Liu, Bo; Y., et al.: Bioorg. Med. Chem., 13, 2451 (2005)
• Lalitha D., et al.: J. Pharm. Biomed. Anal., 50, 710 (2005)