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 
• 81-07-2 saccharin 
• 6155-57-3 sodium saccharinate dihydrate 
• 105-39-5 chloroacetic acid ethyl ester 
• 96-32-2 bromoacetic acid methyl ester 

Downstream Products

• 184971-38-8 methyl (2-hydrazinocarbonylbenzenesulfonylamino)acetate 
• 35511-15-0 methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide 
• 1349170-98-4 2-(2,4,5-trifluorobenzyl)-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide 
• 1349170-99-5 2-[3,5-bis(trifluoromethyl)benzyl]-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide 
• 1349171-00-1 2-[4-(trifluoromethyl)benzyl]-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide 
• 1349171-01-2 2-(4-bromo-2-fluorobenzyl)-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide 
• 1349171-02-3 2-(3-nitrobenzyl)-2H-1,2-benzothiazin-4(3H)-one 1,1-dioxide 
• 1349171-03-4 2-[2-(2,4,5-trifluorobenzyl)-1,1-dioxido-2H-1,2-benzothiazin-4(3H)-ylidene]acetic acid methyl ester 
• 1349171-04-5 2-[2-(3,5-bis(trifluoromethyl)benzyl)-1,1-dioxido-2H-1,2-benzothiazin-4(3H)-ylidene]acetic acid methyl ester 
• 1349171-05-6 2-[2-(4-(trifluoromethyl)benzyl)-1,1-dioxido-2H-1,2-benzothiazin-4(3H)-ylidene]acetic acid methyl ester 
• 1349171-06-7 2-[2-(4-bromo-2-fluorobenzyl)-1,1-dioxido-2H-1,2-benzothiazin-4(3H)-ylidene]acetic acid methyl ester 
• 1349171-09-0 2-[2-(3-nitrobenzyl)-1,1-dioxido-2H-1,2-benzothiazin-4(3H)-ylidene]acetic acid methyl ester 
• 1349171-11-4 2-[2-(2-fluorobenzyl)-1,1-dioxido-2H-1,2-benzothiazin-4(3H)-ylidene]acetic acid methyl ester 
• 1349171-19-2 2-[2-(2,4,5-trifluorobenzyl)-1,1-dioxido-2H-1,2-benzothiazin-4(3H)-ylidene]acetic acid 

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.].

Synthesis, monoamine oxidase inhibition activity and molecular docking studies of novel 4-hydroxy-N′-[benzylidene or 1-phenylethylidene]-2-H/methyl/benzyl-1,2-benzothiazine-3-carbohydrazide 1,1-dioxides

Three series of 4-hydroxy-N′-[benzylidene/1-phenylethylidene]-2-H/methyl/benzyl-1,2-benzothiazine-3-carbohydrazide 1,1-dioxides (9–11)a-l were synthesized and unraveled to be highly potent dual inhibitors of monoamine oxidases (MAO-A and MAO-B). All the examined compounds demonstrated IC50 values in lower micro-molar range for both MAO-A as well as MAO-B. The most active MAO-A inhibitor was 4-hydroxy-N′-(1-phenylethylidene)-2H-benzo[e][1,2]thiazine-3-carbohydrazide 1,1-dioxide (9i) with an IC50 value of 0.11 ± 0.005 μM, whereas, methyl 4-hydroxy-2H-benzo[e][1,2]thiazine-3-carboxylate 1,1-dioxide (3) was the most active MAO-B inhibitor with an IC50 value of 0.21 ± 0.01 μM. Enzyme kinetics studies revealed that the most potent compounds inhibited both MAO enzymes (A & B) in a competitive fashion. Molecular docking studies were also performed to obtain an intuitive picture of inhibition potential for potent inhibitors. The high potency of these compounds is optimally combined with highly favorable ADME profile with predicted good oral bioavailability.

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.