5-fluoro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

• ChemBase ID: 41927
• Molecular Formular: C8H4FNO3
• Molecular Mass: 181.1206632
• Monoisotopic Mass: 181.01752121
• SMILES: c1(=O)oc(=O)[nH]c2c1c(F)ccc2
• Canonical SMILES: O=c1oc(=O)c2c([nH]1)cccc2F
• InChI: InChI=1S/C8H4FNO3/c9-4-2-1-3-5-6(4)7(11)13-8(12)10-5/h1-3H,(H,10,12)
• InChIKey: VAAIGNBVENPUEI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-fluoro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione
• IUPAC Traditional name: 5-fluoro-1H-3,1-benzoxazine-2,4-dione
• Synonyms: 5-Fluoro-2H-3,1-benzoxazine-2,4(1H)-dione; 5-Fluoro-2H-3,1-benzoxazine-2,4(1H)-dione; 5-Fluoro-1H-benzo[d][1,3]oxazine-2,4-dione; 5-Fluoroisatoic anhydride; 6-Fluoro-1H-benzo[d][1,3]oxazine-2,4-dione; 6-Fluoro-2H-3,1-benzoxazine-2,4(1H)-dione; 6-Fluorobenzo[d][1,3]oxazine-2,4-dione; NSC 149815

Database IDs

• CAS Number: 78755-94-9; 321-69-7
• MDL Number: MFCD00112979
• PubChem SID: 162046690
• PubChem CID: 2783057

CALCULATED PROPERTIES

• Acid pKa: 9.270099
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.6187401
• LogD (pH = 7.4): 1.6132839
• Log P: 1.6188102
• Molar Refractivity: 42.0427 cm^3
• Polarizability: 15.087874 Å^3
• Polar Surface Area: 55.4 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Dark yellow Solid
• Melting Point: >200°C (dec.); 230 °C; 230°C
• Density: 1.502

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• Storage Warning: IRRITANT; Irritant
• TSCA Listed: false

Product Information

• Purity: >95%

DETAILS

Toronto Research Chemicals - F592025

5-Fluoroisatoic Anhydride is a versatile pharmaceutical intermediate used in the preparation of insulin secretagogues, HCV polymerase inhibitors, anxiolytic agents and other bioactive compounds.

REFERENCES

• Wright, W.B. et al.: J. Med. Chem., 21, 1087 (1978)
• Cantin, L.D. et al.: Bioorg. Med. Chem. Lett., 17, 2869 (1978)
• Tedesco, R. et al.: J. Med. Chem., 49, 471 (1978)