methyl 4-hydroxy-1,1-dioxo-2H-1λ6,2-benzothiazine-3-carboxylate

• ChemBase ID: 173789
• Molecular Formular: C10H9NO5S
• Molecular Mass: 255.24716
• Monoisotopic Mass: 255.02014339
• SMILES: c1cccc2c1C(=C(NS2(=O)=O)C(=O)OC)O
• Canonical SMILES: COC(=O)C1=C(O)c2c(S(=O)(=O)N1)cccc2
• InChI: InChI=1S/C10H9NO5S/c1-16-10(13)8-9(12)6-4-2-3-5-7(6)17(14,15)11-8/h2-5,11-12H,1H3
• InChIKey: GEUURTZIEGFZAG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 4-hydroxy-1,1-dioxo-2H-1λ^6,2-benzothiazine-3-carboxylate
• IUPAC Traditional name: methyl 4-hydroxy-1,1-dioxo-2H-1λ^6,2-benzothiazine-3-carboxylate
• Synonyms: 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylic Acid Methyl Ester 1,1-Dioxide; Piroxicam Impurity G; Methyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide(Piroxicam Impurity G)

Database IDs

• CAS Number: 35511-14-9
• PubChem SID: 164229699
• PubChem CID: 54676531

CALCULATED PROPERTIES

• Acid pKa: 4.3026986
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.8820352
• LogD (pH = 7.4): -2.3900526
• Log P: 0.3329272
• Molar Refractivity: 60.482 cm^3
• Polarizability: 23.575228 Å^3
• Polar Surface Area: 92.7 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Off-White to Grey Solid
• Melting Point: 168-170°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M312590

Piroxicam impurity G.

REFERENCES

• Lombardino, J., et al.: J. Med. Chem., 14, 1171 (1971)
• Turck, D., et al.: Clin. Pharmacol., 36, 79 (1971)
• Bihovsky, R., et al.: Bioorg. Med. Chem. Lett., 14, 1035 (1971)