35511-15-0

Basic information

• Product Name: 2-METHYL-4-HYDROXY-2H-1,2-BENZOTHIAZINE-3-CARBOXYLIC METHYL ESTER-1,1-DIOXIDE
• Synonyms: Methyl4-hydroxy-2-methyl-2H-1,2-benzothiazine3-carboxylate1,1-dioxide;2-METHYL-4-HYDROXY-2H-1,2-BENZOTHIAZINE-3-CARBOXYLIC METHYL ESTER-1,1-DIOXIDE;2-METHYL-4-HYDROXY-2H-1,2-BENZOTHIAZINE-3-CARBOXYLIC ACID METHYL ESTER 1,1-DIOXIDE;2-Methyl-4-hydroxy-2H-1,2-benzisothiazine-3-carboxylic acid ethyl ester-1,1-diox;2-Methyl-4-Hydroxy-2H-1,2-Benzotiazine-3-CarboxylicAicdEthylEster-1,1-Dioxide;Methyl 4-hydroxy-2-methyl-1,1-dioxo-2H-1,2-benzothiazine-3-carboxylate;4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid methyl ester 1,1-;2-METHYL-4-HYDROXY-2H-1,2-BENZOTHIAZINE-3-CARBOXYLIC METHYL ESTER-1,1-DIOXIDE 98% MIN
• CAS NO: 35511-15-0
• Molecular Formula: C₁₁H₁₁NO₅S
• Molecular Weight: 269.27
• EINECS: 252-601-4
• Product Categories: (intermediate of piroxicam);Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Aromatics;Heterocycles
• Mol File: 35511-15-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: 163-165°C
• Boiling Point: 439.9 °C at 760 mmHg
• Flash Point: 219.8 °C
• Appearance: Off-white to pale yellow solid
• Density: 1.515 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: -20?C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 2-METHYL-4-HYDROXY-2H-1,2-BENZOTHIAZINE-3-CARBOXYLIC METHYL ESTER-1,1-DIOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-4-HYDROXY-2H-1,2-BENZOTHIAZINE-3-CARBOXYLIC METHYL ESTER-1,1-DIOXIDE(35511-15-0)
• EPA Substance Registry System: 2-METHYL-4-HYDROXY-2H-1,2-BENZOTHIAZINE-3-CARBOXYLIC METHYL ESTER-1,1-DIOXIDE(35511-15-0)

Safety Data

• Hazardous Substances Data: 35511-15-0(Hazardous Substances Data)

Usage

Description

2-METHYL-4-HYDROXY-2H-1,2-BENZOTHIAZINE-3-CARBOXYLIC METHYL ESTER-1,1-DIOXIDE, also known as Methyl 4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide, is an organic compound that serves as an impurity in certain pharmaceutical products. It is characterized by its unique chemical structure, which includes a benzothiazine ring, a methyl ester group, and a hydroxyl group.

Uses

Used in Pharmaceutical Industry:
2-METHYL-4-HYDROXY-2H-1,2-BENZOTHIAZINE-3-CARBOXYLIC METHYL ESTER-1,1-DIOXIDE is used as an impurity in the production of Meloxicam (M216100), a nonsteroidal anti-inflammatory drug (NSAID) used for the treatment of various conditions such as osteoarthritis, rheumatoid arthritis, and ankylosing spondylitis. Its presence as an impurity is monitored and controlled to ensure the safety and efficacy of the final pharmaceutical product.

InChI:InChI=1/C11H11NO5S/c1-12-9(11(14)17-2)10(13)7-5-3-4-6-8(7)18(12,15)16/h3-6,13H,1-2H3

Upstream product

• 15448-99-4 N-methylsaccharin 
• 96-34-4 methyl chloroacetate 
• 6639-62-9 methyl 3-oxo-2,3-dihydrobenzo[d][1,2]thiazol-2-acetate 1,1-dioxide 
• 124-41-4 sodium methylate 
• 113412-07-0 methyl 2-(N-methyl-N-(methoxycarbonylmethyl)sulfamoyl)benzoate 
• 85727-15-7 Chloro-(3-hydroxy-2-methyl-1,1-dioxo-2,3-dihydro-1H-1λ⁶-benzo[d]isothiazol-3-yl)-acetic acid methyl ester 
• 35511-14-9 methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide 
• 77-78-1 dimethyl sulfate 
• 76508-33-3 methyl 2- benzoate 
• 74-88-4 methyl iodide 
• 128-44-9 saccharin sodium salt 
• 81-07-2 saccharin 
• 111-84-2 nonane 

Downstream Products

• 5510-10-1 2-methyl-2H-1,2-benzothiazine-4-(3H)-one-1,1-dioxyde 
• 34042-85-8 sudoxicam 
• 34552-84-6 isoxicam 
• 71125-38-7 meloxicam 
• 34258-79-2 4-hydroxy-2-methyl-N-phenyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide 
• 36322-90-4 Piroxicam 
• 914782-21-1 N-(2-carbamoylphenyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide 
• 208051-74-5 N-(2-methyl-4-methoxy-2H-1,2-benzothiazine-3-carbonyl)-L-phenylalaninol 1,1-dioxide 
• 67-56-1 methanol 
• 892395-41-4 4-hydroxy-2-methyl-N-methyl-(5-methyl-2-thiazolyl)-2H-l,2-benzothiazine-3-carboxamide-1,1-dioxide 
• 35511-63-8 N-(4'-chlorophenyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide 
• 35511-70-7 N-(2-chlorophenyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide 
• 1145656-36-5 N-[3,5-dimethyl-1,3-thiazol-2(3H)-ylidene]-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide 
• 1221971-36-3 C₂₂H₁₆Cl₂N₂O₄S 

Relevant articles and documents

A facile one-pot synthesis of 4-hydroxy-3-methoxycarbonyl-2-methyl-2H-1,2-benzothiazine 1,1-dioxide, a key intermediate in the synthesis of oxicam anti-inflammatory agents

4-Hydroxy-3-methoxycarbonyl-2-methyl-2H-1,2-benzothiazine 1,1-dioxide (8) was synthesized by a one-pot procedure, starting from the readily available saccharine. The synthesis involves 4 transformations with an overall yield equivalent to that from the stepwise process.

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.

Microwave assisted synthesis and structure-activity relationship of 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl-1,2-benzothiazine-3- carbohydrazide 1,1-dioxides as anti-microbial agents

A series of 4-hydroxy-N′-[1-phenylethylidene]-2H/2-methyl, 1,2-benzothiazine-3-carbohydrazide 1,1-dioxides was synthesized from commercially available sodium saccharin. Base catalyzed ring expansion of methyl (1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)acetate followed by ultrasound mediated hydrazinolysis and subsequent reaction with 1-phenylethanones under the influence of microwaves yielded the title compounds. Besides, microwave assisted synthesis of 1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide and 4-methyl-1,4-dihydropyrazolo[4,3-c][1,2]benzothiazin-3-ol 5,5-dioxide is also discussed. Most of the synthesized compounds were found to possess moderate to significant anti-microbial (anti-bacterial and anti-fungal) activities. It is found that compounds with greater lipophilicity (N-methyl analogues) possessed higher anti-bacterial activities.

Synthesis of potential biologically active 1,2-benzothiazin-3-yl- quinazolin-4(3H)-ones

A series of potential biologically active 2-(4-hydroxy-1,1-dioxido-2H-1,2- benzothiazin-3-yl)quinazolin-4(3H)-ones was synthesized in a straight forward manner by condensation of respective 4-hydroxy-1,2-benzothiazine-1,1-dioxides with anthranilamide followed by simple and high throughput cyclization of N-[2-(aminocarbonyl) phenyl]-4-hydroxy-1,2-benzothiazine-3-carboxamide-1,1- dioxides. All the synthesized compounds were subjected to preliminary evaluation for their biological activity against Gram positive and Gram negative bacteria. Some of the assayed compounds showed marked activity against Bacillus subtilis.