53440-57-6

Basic information

• Product Name: 3-phenyl-1,2-benzisothiazole 1,1-dioxide
• Synonyms: 3-phenyl-1,2-benzisothiazole 1,1-dioxide
• CAS NO: 53440-57-6
• Molecular Formula: C₁₃H₉NO₂S
• Molecular Weight: 243.28106
• Mol File: 53440-57-6.mol
• Article Data: 27

Chemical Properties

• Melting Point: 315 °C
• Boiling Point: 438.6±28.0 °C(Predicted)
• Appearance: /
• Density: 1.34±0.1 g/cm3(Predicted)
• PKA: -4.09±0.20(Predicted)
• CAS DataBase Reference: 3-phenyl-1,2-benzisothiazole 1,1-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyl-1,2-benzisothiazole 1,1-dioxide(53440-57-6)
• EPA Substance Registry System: 3-phenyl-1,2-benzisothiazole 1,1-dioxide(53440-57-6)

Safety Data

• Hazardous Substances Data: 53440-57-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 57, p. 5328, 1992 DOI: 10.1021/jo00046a012

Upstream product

• 54075-06-8 2-benzoyl-benzenesulfonyl chloride 
• 1709-51-9 N,N-diphenylbenzenesulfonamide 
• 100-47-0 benzonitrile 
• 7446-70-0 aluminium trichloride 
• 71-43-2 benzene 
• 57683-71-3 methyl 2-(aminosulfonyl)benzoate 
• 591-51-5 phenyllithium 
• 98-10-2 benzenesulfonamide 
• 100-52-7 benzaldehyde 
• 136701-86-5 (±)-3-phenyl-1,2-benzisothiazoline 1,1-dioxide 
• 81-07-2 saccharin 
• 106380-99-8 1,1-dioxo-3-phenyl-2,3-dihydro-1λ⁶-benz[d]isothiazol-3-ol 
• 124401-11-2 7b-phenyl-7bH-oxazirino<2,3-b><1,2>benzisothiazole 3,3-dioxide 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 124401-11-2 7b-phenyl-7bH-oxazirino<2,3-b><1,2>benzisothiazole 3,3-dioxide 
• 61766-87-8 2-((Z)-3-Diethylamino-2-methyl-1-phenyl-propenyl)-benzenesulfonamide 
• 1269473-37-1 1,9b-diphenyl-1,2-dihydrobenzo[d]pyrrolo[1,2-b]isothiazol-3-one 5,5-dioxide 
• 1093168-66-1 rac-9b-phenyl-1,2-dihydrobenzo[d]pyrrolo[1,2-b]isothiazol-3-one 5,5-dioxide 
• 1365284-18-9 C₂₂H₂₁NO₅S 
• 1365284-16-7 C₂₀H₁₅NO₄S 
• 1365284-12-3 (R)-3-(4-methoxyphenyl)-3-phenyl-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide 
• 1365284-06-5 C₂₀H₁₇NO₂S 
• 1365284-28-1 (S)-3-phenyl-3-(p-tolyl)-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide 
• 1365284-10-1 C₂₀H₁₇NO₂S 
• 1365284-08-7 (R)-3-phenyl-3-(m-tolyl)-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide 
• 1365284-22-5 C₁₉H₁₄FNO₂S 
• 1365284-24-7 C₁₉H₁₄ClNO₂S 
• 1365284-14-5 C₂₀H₁₇NO₃S 

Relevant articles and documents

The Preparation of 3-Substituted 1,2-Benzisothiazole 1,1-Dioxides from Lithiated Intermediates or Grignard Reagents and Methyl 2-(Aminosulfonyl)benzoate

A polylithiated β-ketoester, β-diketone, or β-ketoamide was condensed-cyclized with lithiated methyl 2-(Aminosulfonyl)benzoate, to afford new 3-substituted 1,2-benzisothiazole 1,1-dioxides. Some Grignard or organolithium reagents were also condensed-cyclized with methyl 2-(aminosulfonyl)benzoate to give 3-substituted 1,2-benzisothiazole 1,1-dioxides.

Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures

We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.

Palladium-Catalyzed ortho-Benzoylation of Sulfonamides through C?H Activation: Expedient Synthesis of Cyclic N-Sulfonyl Ketimines

The ortho-carbonylation of sulfonylarenes by non-hazardous aryl aldehydes as a carbonyl precursor was reported. In this method, the sulfonamide group serves as a directing group for C?H activation in the presence of a Pd catalyst under ligand-free conditions. The scope of this strategy has been extended to the one-pot two-step synthesis of cyclic N-sulfonyl ketimines under mild reaction conditions. Our approach could be considered as an alternative by circumventing the use of highly reactive organolithium or Grignard reagents to access a wide range of biologically potent cyclic N-sulfonyl ketimines. (Figure presented.).