6639-62-9

Basic information

• Product Name: methyl 3-oxo1,2-benzisothiazole-2(3H)-acetate 1,1-dioxide
• Synonyms: methyl 3-oxo1,2-benzisothiazole-2(3H)-acetate 1,1-dioxide;2,3-DIHYDRO-3-OXO-1,2-BENZOISOTHIAZOLE-2-ACETIC ACID METHYL ESTER 1,1-DIOXIDE;3-Oxo-1,2-benzoisothiazole-2(3H)acetic acid methyl ester,1-dioxide;3-Oxo-1,2-benzoisothiazoline-2-acetic Acid Methyl Ester 1,1-Dioxide (Piroxicam Impurity D);Einecs 229-646-3;NSC 49216;PiroxicaM IMpurity D;Saccharin N-(2-Acetic Acid Methyl Ester)
• CAS NO: 6639-62-9
• Molecular Formula: C₁₀H₉NO₅S
• Molecular Weight: 255.24716
• EINECS: 229-646-3
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 6639-62-9.mol
• Article Data: 22

Chemical Properties

• Melting Point: 121-123℃
• Boiling Point: 434.5°C at 760 mmHg
• Flash Point: 216.6°C
• Appearance: /
• Density: 1.499g/cm³
• Vapor Pressure: 9.45E-08mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: Refrigerator
• CAS DataBase Reference: methyl 3-oxo1,2-benzisothiazole-2(3H)-acetate 1,1-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-oxo1,2-benzisothiazole-2(3H)-acetate 1,1-dioxide(6639-62-9)
• EPA Substance Registry System: methyl 3-oxo1,2-benzisothiazole-2(3H)-acetate 1,1-dioxide(6639-62-9)

Safety Data

• Hazardous Substances Data: 6639-62-9(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Piroxicam impurity D.

InChI:InChI=1/C10H9NO5S/c1-16-9(12)6-11-10(13)7-4-2-3-5-8(7)17(11,14)15/h2-5H,6H2,1H3

Upstream product

• 128-44-9 saccharin sodium salt 
• 96-34-4 methyl chloroacetate 
• 96-32-2 bromoacetic acid methyl ester 
• 81-07-2 saccharin 
• 6155-57-3 sodium saccharinate dihydrate 
• 105-39-5 chloroacetic acid ethyl ester 

Downstream Products

• 1205-08-9 methyl hippurate 
• 35511-14-9 methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide 
• 107124-71-0 4-Hydroxy-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazine-3-carboxylic acid 2-ethoxy-ethyl ester 
• 80201-73-6 2-methoxyethyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide 
• 76508-33-3 methyl 2- benzoate 
• 35511-15-0 methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide 
• 24683-21-4 4-hydroxy-2H-1,2-benzothiazine-3-carboxylic acid ethyl ester 1,1-dioxide 
• 76508-35-5 isopropyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide 
• 76508-36-6 4-Hydroxy-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[e][1,2]thiazine-3-carboxylic acid tert-butyl ester 
• 128328-83-6 3,3-Bis-benzylsulfanyl-2-(1,1,3-trioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-acrylic acid methyl ester 
• 113412-07-0 methyl 2-(N-methyl-N-(methoxycarbonylmethyl)sulfamoyl)benzoate 
• 52188-11-1 2-(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)acetic acid 
• 220223-03-0 N-(2-carboxyphenylsulfonyl)glycine 
• 184971-38-8 methyl (2-hydrazinocarbonylbenzenesulfonylamino)acetate 

Relevant articles and documents

Synthesis, cytotoxic and antioxidant activities of azolyl benzothiazine carboxamides

Abstract: Azolyl benzothiazine carboxamides were prepared from benzothiazine carboxylate and azolyl amines in the presence of NaOMe under ultrasonication. 4-Bromothiophenylimidazolyl benzothiazine carboxamide (19b) and 4-bromopyrrolylimidazolyl benzothiazine carboxamide (22b) showed cytotoxic activity on HeLa cell lines (IC50 33.75, 47.52?μM) and MCF-7 cell lines (IC5031.75, 34.35?μM). Furthermore, methyl-substituted furanyloxazolyl benzothiazine carboxamide (14a), furanylimidazolyl benzothiazine carboxamide (16a), thiophenyloxazolyl benzothiazine carboxamide (17a) and pyrrolyloxazolyl benzothiazine carboxamide (20a) exhibited antioxidant activity greater than ascorbic acid. Graphical abstract: Azolyl benzothiazine carboxamides are prepared from benzothiazine carboxylate and azolyl amines. Optimization of reaction conditions is established using different molar concentrations of NaOMe. Compounds 19b and 22b showed cytotoxic activity on HeLa cell lines and MCF-7 cell lines. Compounds 14a, 16a, 17a and 20a exhibited prominent antioxidant activity.[Figure not available: see fulltext.].

Hybrid compounds from chalcone and 1,2-benzothiazine pharmacophores as selective inhibitors of alkaline phosphatase isozymes

Chalcones and 1,2-benzothiazines are two important classes of bioactive compounds, each scaffold endowed with diverse pharmacological activities. Combining both of these pharmacophores in a single molecule was aimed to yield multi-modal agents. Herein, we report a series of hybrid compounds 3a–3o derived from chalcones and 1,2-benzothiazine cores. They were synthesized from commercially available sodium saccharin, and the resulting 1,2-benzothiazine-derived ketone was then condensed with aromatic aldehydes in an aldol condensation to obtain the respective chalcones. The compounds were characterized using different analytical techniques including FT-IR, NMR spectroscopy, mass spectrometry and X-ray crystallography. Some synthesized chalcones revealed potent and/or selective inhibitory properties towards alkaline phosphatase isozymes transiently expressed in COS-7 cells. A detailed structure-activity and selectivity study was carried out with regard to the effect of different substituents at ortho-, meta- and para-positions of the phenyl residue. Compound 3c was the most effective human intestinal alkaline phosphatase (h-IAP) inhibitor (IC50 value of 1.04 μM), while it was not active against human tissue non-specific alkaline phosphatase (h-TNAP) isozyme. In contrast, 3i was a selective inhibitor of h-TNAP with IC50 values of 0.25 ± 0.01 μM. The possible binding interactions of the most effective inhibitors of h-TNAP and h-IAP were obtained from molecular docking studies.

Stereopure Functionalized Benzosultams via Ruthenium(II)-Catalyzed Dynamic Kinetic Resolution-Asymmetric Transfer Hydrogenation

A highly diastereo- and enantioselective Ru(II)-catalyzed dynamic kinetic resolution-asymmetric transfer hydrogenation (DKR-ATH) of α-(N-sulfonylimino) and α-(N-sulfonylamino) aryl ketones to 4-hydroxy-benzo-δ- and 3-(α-hydroxy-arylmethyl)-benzo-γ-sultams is presented. By employing enantiopure ansa-Ru[PipSO2DPEN(CH2)4Ph] cat. II with S/C = 10 000 in a HCO2H/Et3N binary mix, up to >99.9% ee and dr >99:1 are obtained with 100% conversion under mild conditions. Application to access the stereopure "structurally simplified TsDPEN" N,N-ligand syn-3-(α-aminobenzyl)-benzo-γ-sultam ("syn-ULTAM") and its structural isomer trans-4-amino-3-phenyl-benzo-δ-sultam (trans-4) is demonstrated.