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

• ChemBase ID: 150723
• Molecular Formular: C12H13NO5S
• Molecular Mass: 283.30032
• Monoisotopic Mass: 283.05144352
• SMILES: CCOC(=O)C1=C(c2ccccc2S(=O)(=O)N1C)O
• Canonical SMILES: CCOC(=O)C1=C(O)c2ccccc2S(=O)(=O)N1C
• InChI: InChI=1S/C12H13NO5S/c1-3-18-12(15)10-11(14)8-6-4-5-7-9(8)19(16,17)13(10)2/h4-7,14H,3H2,1-2H3
• InChIKey: QWTNANUGXZEPFQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-hydroxy-2-methyl-1,1-dioxo-2H-1λ^6,2-benzothiazine-3-carboxylate
• IUPAC Traditional name: ethyl 4-hydroxy-2-methyl-1,1-dioxo-1λ^6,2-benzothiazine-3-carboxylate
• Synonyms: Ethyl 4-hydroxy-2-methyl-1,1-dioxo-2H-1,2-benzothiazine-3-carboxylate; 4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic Acid Ethyl Ester 1,1-Dioxide; Piroxicam Impurity K; Ethyl 4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide(Piroxicam Impurity K); 4-羟基-2-甲基-2H-1,2-苯并噻嗪-3-甲酸乙酯 1,1-二氧化物

Database IDs

• CAS Number: 24683-26-9
• EC Number: 246-403-7
• MDL Number: MFCD00190168
• PubChem SID: 24879268; 162244884
• PubChem CID: 54679348

CALCULATED PROPERTIES

• Acid pKa: 4.421373
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.1923804
• LogD (pH = 7.4): -1.6836898
• Log P: 0.9134112
• Molar Refractivity: 70.1273 cm^3
• Polarizability: 27.2213 Å^3
• Polar Surface Area: 83.91 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 140-143°C; 140-144 °C(lit.)

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: DL0710425
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 23
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H331
• GHS Precautionary statements: P261-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C12H13NO5S

DETAILS

Sigma Aldrich - 552429

Packaging
25 g in glass bottle

Toronto Research Chemicals - E918980

Piroxicam impurity K. Also an impurity found in meloxicam (M216100).

REFERENCES

• Meng, L., et al.: Biochemistry, 41, 7199 (1989)
• Luo, Q., et al.: J. Med. Chem., 2631 (1989)
• Chang, S., et al.: J. Bacteriol., 71, 4071 (1989)
• Tahirov, T., et al.: J. Mol. Biol., 284, 101 (1989)