2,2-dichloro-N-[(1R,2S)-3-fluoro-1-hydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide

• ChemBase ID: 157740
• Molecular Formular: C12H14Cl2FNO4S
• Molecular Mass: 358.2132632
• Monoisotopic Mass: 357.00046251
• SMILES: CS(=O)(=O)c1ccc(cc1)[C@H]([C@@H](CF)NC(=O)C(Cl)Cl)O
• Canonical SMILES: FC[C@H]([C@@H](c1ccc(cc1)S(=O)(=O)C)O)NC(=O)C(Cl)Cl
• InChI: InChI=1S/C12H14Cl2FNO4S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-15)16-12(18)11(13)14/h2-5,9-11,17H,6H2,1H3,(H,16,18)/t9-,10-/m1/s1
• InChIKey: AYIRNRDRBQJXIF-NXEZZACHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-dichloro-N-[(1R,2S)-3-fluoro-1-hydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide
• IUPAC Traditional name: florfenicol
• Synonyms: Florfenicol; SCH-25298; Aquafen; Nuflor; [R-(R*,S*)]-2,2-Dichloro-N-[1-(fluoromethyl)-2-hydroxy-2-[4-(methylsulfonyl)phenyl]ethyl]acetamide; 2,2-Dichloro-N-[(1S,2R)-1-(fluoromethyl)-2-hydroxy-2-[4-(methylsulfonyl)phenyl]ethyl]acetamide; (-)-Florfenicol; Aquaflor; Florfenicol; Sch 25298; Florfenicol; [R-(R*,S*)]-2,2-二氯-N-[1-(氟代甲基)-2-羟基-2-[4-(甲磺酰基)苯基]乙基]乙酰胺; 氟洛芬; 氟苯尼考; 氟苯尼考

Database IDs

• CAS Number: 73231-34-2
• MDL Number: MFCD00864834
• PubChem SID: 162251877
• PubChem CID: 114811

CALCULATED PROPERTIES

• Acid pKa: 6.8353424
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.65278643
• LogD (pH = 7.4): 0.15264378
• Log P: 0.67011964
• Molar Refractivity: 78.1875 cm^3
• Polarizability: 31.014837 Å^3
• Polar Surface Area: 83.47 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: solid; White Crystalline Powder
• Melting Point: 152-154°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Grade: analytical standard, for drug analysis
• Empirical Formula (Hill Notation): C12H14Cl2FNO4S

DETAILS

Sigma Aldrich - F1427

Application
Antibacterial.

Toronto Research Chemicals - F405750

Florfenicol is a fluorinated derivative of thiamphenicol. Florfenicol inhibits bacterial protein synthesis by binding to ribosome 50S and 70S subunits. Florfenicol is used as an antibacterial.

REFERENCES

• Kim, E and Aoki, T.: Microbiol. Immunol., 40, 665, (1996)
• Keyes, K.: Antimicrob. Agents Chemother., 44, 421 (2000)