15448-99-4

Basic information

• Product Name: N-METHYLSACCHARIN
• Synonyms: RARECHEM AM UC 0206;N-METHYLSACCHARIN;2-methyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide;2,3-Dihydro-2-methyl-3-oxo-1,2-benzisothiazole 1,1-dioxide;1,2-Benzisothiazol-3(2H)-one, 2-methyl-, 1,1-dioxide;1,2-Benzisothiazolin-3-one, 2-methyl-, 1,1-dioxide;2-Methyl-1,2-benzisothiazole-3(2H)-one-1,1-dioxide;Nsc39120
• CAS NO: 15448-99-4
• Molecular Formula: C₈H₇NO₃S
• Molecular Weight: 197.21
• EINECS: 239-466-7
• Mol File: 15448-99-4.mol

Chemical Properties

• Melting Point: 131 °C
• Boiling Point: 366.3°Cat760mmHg
• Flash Point: 175.3°C
• Appearance: /
• Density: 1.486g/cm³
• Vapor Pressure: 1.48E-05mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -12.83±0.20(Predicted)
• CAS DataBase Reference: N-METHYLSACCHARIN(CAS DataBase Reference)
• NIST Chemistry Reference: N-METHYLSACCHARIN(15448-99-4)
• EPA Substance Registry System: N-METHYLSACCHARIN(15448-99-4)

Safety Data

• Hazardous Substances Data: 15448-99-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 16, p. 1582, 1951 DOI: 10.1021/jo50004a014

InChI:InChI=1/C8H7NO3S/c1-9-8(10)6-4-2-3-5-7(6)13(9,11)12/h2-5H,1H3

Upstream product

• 2527-58-4 2,2'-dithiobis(N-methylbenzamide) 
• 34684-21-4 2-chlorosulfonylbenzoyl chloride 
• 74-89-5 methylamine 
• 128-44-9 saccharin sodium salt 
• 74-88-4 methyl iodide 
• 19298-35-2 (2-methyl-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-ylidene)-phenyl-amine 
• 124-38-9 carbon dioxide 
• 5183-78-8 methyl(phenylsulfonyl)amide 
• 19298-37-4 2-methylsulfamoyl-N-phenyl-benzamide 
• 109-72-8 n-butyllithium 
• 4231-35-0 methyl(diethylamino)acetylene 
• 81-07-2 saccharin 
• 13440-22-7 N-methyl(o-methyl)benzenesulfonamide 
• 26638-43-7 2-methoxycarbonylbenzenesulfonyl chloride 

Downstream Products

• 35511-15-0 methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide 
• 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 
• 256222-57-8 2-Cyano-3-(2-methylsulfamoyl-phenyl)-3-oxo-propionic acid ethyl ester 
• 79672-26-7 methyl 2-<(dimethylamino)sulfonyl>benzoate 
• 111294-72-5 benzoyl-(2-benzoyloxymethyl-benzenesulfonyl)-methyl-amine 
• 36322-90-4 Piroxicam 
• 79672-25-6 3-(2-Dimethylsulfamoyl-phenyl)-N-(5-methyl-isoxazol-3-yl)-3-oxo-propionamide 
• 79672-28-9 3-(2-Dimethylsulfamoyl-phenyl)-3-oxo-propionic acid methyl ester 
• 79672-29-0 2-(2-Methanesulfinyl-acetyl)-N,N-dimethyl-benzenesulfonamide 
• 79672-27-8 2-acetyl-N,N-dimethylbenzenesulfonamide 
• 884862-80-0 methyl 2-[2-(hydroxymethyl)-N-methylphenylsulfonamido] acetate 
• 884862-81-1 methyl 2-[2-(bromomethyl)-N-methylphenylsulfonamido] acetate 
• 125372-22-7 2-methylsulfamoyl-benzoic acid 
• 40431-34-3 2-(hydroxymethyl)-N-methylbenzenesulfonamide 

Relevant articles and documents

New ring systems from 1,2-benzisothiazole-1,1-dioxides and related compounds

Ring-expansions and ring-annulations based on 3-substituted 1,2-benzisothiazole-1,1-dioxides have lead to a variety of novel heterocyclic systems. The reaction of 3-substituted (1H)-1-isoindoles with 1-diethylamino-1-propyne has also resulted in new, ring-expanded molecules in good to modest yields.

Reaction of orthto-lithiated N-methylbenzamide with 1,2-Diketones: A novel highly efficient route to N-methylisoquinolin-1-one

1,2-Diketones were found to react with ortho-lithlated N-methylbenzamide to give diols 4a-g in 59-80% yields. Reaction of diols 4a-g with the system Me3SiCl/Nal in MeCN furnished N-methylisoquinolin-1-ones in 84-92% yields.

Decarbonylative C-C bond-forming reactions of saccharins by nickel catalysis: Homocoupling and cycloaddition

Decarbonylation of saccharins by nickel catalysis enables two kinds of C-C bond-forming reactions; homocoupling of saccharins to form biaryls and cycloaddition with alkynes to form benzosultams. The former represents the first reported nickel-catalyzed decarbonylative C-C homocoupling reaction, whereas the latter constitutes a powerful method to pharmaceutically relevant benzosultams. The reactions proceed with good functional-group tolerance and excellent regioselectivity.

Direct preparation of saccharin skeletons from N-methyl(o-methyl)arenesulfonamides with (diacetoxyiodo)arenes

Various N-methylsaccharins were easily prepared in moderate to good yields by the reaction of N-methyl(o-methyl)arenesulfonamides with (diacetoxyiodo)arene in the presence of iodine under irradiation with a tungsten lamp. The present method is very useful for the direct preparation of saccharins with N-methyl(o-methyl)arenesulfonamides containing various substituents on the aromatic ring.

The Chapman-type rearrangement in pseudosaccharins: The case of 3-(methoxy)-1,2-benzisothiazole 1,1-dioxide

The thermal Chapman-type rearrangement of the pseudosaccharin 3-(methoxy)-1,2-benzisothiazole 1,1-dioxide (MBID) into 2-methyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (MBIOD) was investigated on the basis of computational models and knowledge of the structure of the reactant and product in the isolated and solid phases. X-ray diffraction was used to obtain the structure of the substrate in the crystalline phase, providing fundamental structural data for the development of the theoretical models used to investigate the reaction mechanism in the condensed phase. The intra- and different intermolecular mechanisms were compared on energetic grounds, based on the various developed theoretical models of the rearrangement reactions. The energetic preference (ca. 3.2 kJ mol-1, B3LYP/6-31+G(d,p)) of inter- over intramolecular transfer of the methyl group is predicted for the quasi-simultaneous transfer of the methyl groups model, explaining the potential of MBID towards [1,3′]-isomerization to MBIOD in the condensed phases. The predicted lower energy of MBIOD relative to MBID (ca. 60 kJ mol-1), due to the lower steric hindrance in the MBIOD molecule, acts as a molecular motor for the observed thermal rearrangement.

First observation of Chapman rearrangement of a pseudosaccharyl ether in the solid state: the thermal isomerization of 3-(methoxy)-1,2-benzisothiazole 1,1-dioxide revisited

3-(Methoxy)-1,2-benzisothiazole 1,1-dioxide, a pseudosaccharyl ether, was long ago known to undergo a thermal Chapman-like [1,3′]-isomerization to the corresponding N-methyl pseudosaccharin at temperatures above its melting point (ca. 184 °C) [Hettler H., Tetrahedron Lett. 1968, 15, 1793]. In the present study, it is shown that this rearrangement can also take place in the solid state, at temperatures as low as 150 °C. This was the first observation of a Chapman-like [1,3′]-isomerization in pseudosaccharyl ethers in the solid state. The study has been carried out by a multidisciplinary approach using temperature dependent infrared spectroscopy, differential scanning calorimetry (DSC), and polarized light thermomicroscopy, complemented by theoretical methods.

MODIFIED PROTEINS AND PROTEIN DEGRADERS

Provided herein are compounds, pharmaceutical compositions, and methods for binding or degrading target proteins. Further provided herein are compounds having a DNA damage-binding protein 1 (DDB1) binding moiety. Some such embodiments include a linker. Some such embodiments include a target protein binding moiety. Further provided herein are ligand-DDB1 complexes. Further provided herein are in vivo modified DDB1 proteins.

Synthetic method for preparing saccharin (by machine translation)

1,2 - Benzisothiazol -3 - ketone compounds are subjected to an oxidation reaction with an oxidizing agent, and an oxidizing agent oxidizes thioether of 1,2 - benzisothiazol -3 -one compound to thioamide to obtain the O-benzoyl sulfamide compound. Compared with the traditional production technology of saccharin, the saccharin synthesis method has the advantages of simple process, low cost, high separation efficiency, low pollution and the like, and accords with the green chemistry. (by machine translation)

Bu4NI-Catalyzed, Radical-Induced Regioselective N-Alkylations and Arylations of Tetrazoles Using Organic Peroxides/Peresters

Bu4NI-catalyzed regioselective N2-methylation, N2-Alkylation, and N2-Arylation of tetrazoles have been achieved using tert-butyl hydroperoxide (TBHP) as the methyl source, alkyl diacyl peroxides as the primary alkyl source, alkyl peresters as the secondary and tertiary alkyl sources, and aryl diacyl peroxides as the arylating source. These reactions proceed without pre-functionalization of tetrazole and in the absence of any metal catalysts. Here, peroxides serve the dual role of oxidants as well as alkylating or arylating agents. Based on DFT calculations, it was found that spin density, transition-state barriers (kinetic control), and thermodynamic stability of the products (thermodynamic control) play essential roles in the observed regioselectivity during N-Alkylation. This radical-mediated process is amenable to a broad range of substrates and provides products in moderate to good yields.

Synthesis of (e)-n-substituted 1,2-benzothiazol-3(2h)-imine 1,1-dioxide derivatives from secondary benzenesulfonamides and isothiocyanates

A new and simple method for the preparation of (E)-N-substituted 1,2-benzothiazol-3(2H)-imine 1,1-dioxide derivatives has been developed. 2,N-Dilithiobenzenesulfonamides, generated by the treatment of secondary benzenesulfonamides with two equivalents of butyllithium, react with isothiocyanates to afford the corresponding 2-(aminosulfonyl)benzothioamides, which undergo ring closure with a formal elimination of hydrogen sulfide on treatment with thionyl chloride in the presence of two equivalents of pyridine to provide the desired products. Acid hydrolysis of some of these products leads to the formation of N-substituted saccharins.