351186-42-0

Basic information

• Product Name: N‐morpholinobenzenesulfonamide
• Synonyms: N‐morpholinobenzenesulfonamide
• CAS NO: 351186-42-0
• Molecular Weight: 242.299
• Mol File: 351186-42-0.mol

Chemical Properties

• CAS DataBase Reference: N‐morpholinobenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N‐morpholinobenzenesulfonamide(351186-42-0)
• EPA Substance Registry System: N‐morpholinobenzenesulfonamide(351186-42-0)

Safety Data

• Hazardous Substances Data: 351186-42-0(Hazardous Substances Data)

Upstream product

• 4319-49-7 1-aminomorpholine 
• 25628-11-9 phenyl 1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonate 
• 144930-50-7 mesityl(phenyl)iodonium triflouromethanesulfonate 
• 312727-69-8 phenyl(2,4,6-triisopropylphenyl)iodonium trifluoromethanesulfonate 
• 115298-63-0 phenyl(4-methoxyphenyl)iodonium triflate 
• 1449510-54-6 2,4-dimethoxyphenyl(phenyl)iodonium triflate 
• 936326-60-2 phenyl(2,4,6-trimethoxyphenyl)iodonium 4-methylbenzenesulfonate 
• 66003-76-7 Diphenyliodonium triflate 
• 1483-72-3 diphenyliodonium chloride 
• 58109-40-3 diphenyliodonium hexafluorophosphate 
• 98-09-9 benzenesulfonyl chloride 
• 2553-19-7 diethoxydiphenylsilane 
• 780-69-8 triethoxyphenylsilane 
• 16978-76-0 1-phenyl-2-(piperidin-1-yl)diazene 

Downstream Products

• 3112-88-7 Benzyl phenyl sulfone 
• 1225327-16-1 5-(2-(phenylsulfonyl)ethyl)-1H-indole 

Relevant articles and documents

Structure–activity relationships (SARs) of α- ketothioamides as inhibitors of phosphoglycerate dehydrogenase (PHGDH)

For many years now, targeting deregulation within cancer cells’ metabolism has appeared as a promising strategy for the development of more specific and efficient cancer treatments. Recently, numerous reports highlighted the crucial role of the serine synthetic pathway, and particularly of the phosphoglycerate dehydrogenase (PHGDH), the first enzyme of the pathway, to sustain cancer progression. Yet, because of very weak potencies usually in cell-based settings, the inhibitors reported so far failed to lay ground on the potential of this approach. In this paper, we report a structure–activity relationship study of a series of α-ketothioamides that we have recently identified. Interestingly, this study led to a deeper understanding of the structure–activity relationship (SAR) in this series and to the identification of new PHGDH inhibitors. The activity of the more potent compounds was confirmed by cellular thermal shift assays and in cell-based experiments. We hope that this research will eventually provide a new entry point, based on this promising chemical scaffold, for the development of therapeutic agents targeting PHGDH.

Visible-Light Photoredox-Catalyzed Aminosulfonylation of Diaryliodonium Salts with Sulfur Dioxide and Hydrazines

A photoredox-catalyzed three-component synthesis of N-aminosulfonamides starting from diaryliodonium salts, hydrazines and sulfur dioxide is reported. This reaction proceeds under mild conditions at room temperature and is driven by visible light. A simple bisulfite salt can be used as a readily available and easy-to-handle sulfur dioxide source. Mechanistic studies support a catalytic photoredox pathway with the diaryliodonium salt as convenient source for aryl radicals. (Figure presented.).

The Design of an In-Ex Tube for Gas Related Organic Reactions

Here, an interesting in-ex tube was designed for gas-related organic reactions. By using this specially designed reaction tube, several gas-reliant organic reactions are applicable, including CO, SO2, and H2. Moderate to good yields of the desired products were produced easily.

A palladium-catalyzed coupling reaction of aryl nonaflates, sulfur dioxide, and hydrazines

A facile route to synthesise N-aminosulfonamides through a palladium-catalyzed coupling reaction of aryl nonaflates, sulfur dioxide, and hydrazines is reported. This transformation proceeds in the presence of Pd(OAc)2/XantPhos, and TBAB in 1,4-dioxane at 80°C, leading to the corresponding N-aminosulfonamides in moderate to good yields. The reaction scope has been demonstrated, and good functional tolerance is observed. A plausible mechanism is proposed through the insertion of sulfur dioxide.

A copper-catalyzed three-component reaction of triethoxysilanes, sulfur dioxide, and hydrazines

A three-component reaction of triethoxysilanes, sulfur dioxide, and hydrazines catalyzed by copper(II) acetate is reported, leading to N-aminosulfonamides in good yields. Not only triethoxy(aryl)silanes but also triethoxy(alkyl)silanes are compatible during the process of insertion of sulfur dioxide. Additionally, diethoxydiarylsilanes are suitable under the conditions as well.

Catalytic conversion of aryl triazenes into aryl sulfonamides using sulfur dioxide as the sulfonyl source

Various sulfonamides have been synthesized from triazenes and sulfur dioxide. In the presence of just a catalytic amount of BF3· OEt2, a series of 1-aryl-triazenes were converted into sulfonyl hydrazines in good to excellent yields. When using CuCl2 as the catalyst, the corresponding sulfonamides can be produced from the 1-aryl triazenes in good yields. This journal is the Partner Organisations 2014.

Aminosulfonylation of aromatic amines, sulfur dioxide and hydrazines

A facile route to aryl N-aminosulfonamides under mild conditions is provided. The reaction of aromatic amines (including heteroaromatic amines), sulfur dioxide, and hydrazines proceeds efficiently with good functional group tolerance. The in situ generated diazonium ion is involved in the aminosulfonylation process. This journal is the Partner Organisations 2014.

Metal-free aminosulfonylation of aryldiazonium tetrafluoroborates with DABCO×(SO2)2 and hydrazines

The coupling of aryldiazonium tetrafluoroborates, DABCO×(SO 2)2, and hydrazines under metal-free conditions leads to the formation of aryl N-aminosulfonamides. The reaction proceeds smoothly at room temperature and shows broad functional-group tolerance. A radical process is proposed for this transformation. The coupling of aryldiazonium tetrafluoroborates, DABCO×(SO2)2, and hydrazines under metal-free conditions leads to the formation of aryl N-aminosulfonamides. The reaction proceeds under mild reaction conditions, is fast, has a broad substrate scope, and gives the products in high yiels (21 examples). A plausible mechanism that involves a radical process is also proposed. Copyright

One-pot three-component sulfone synthesis exploiting palladium-catalysed aryl halide aminosulfonylation

A palladium-catalysed aminosulfonylation process is used as the key-step in a one-pot, three-component sulfone synthesis. The process combines aryl-, heteroaryl- and alkenyl iodides with a sulfonyl unit and an electrophilic coupling fragment. The sulfonyl unit is delivered in the form of an aminosulfonamide, which then serves as a masked sulfinate. The sulfinate is combined, in situ, with an electrophilic coupling partner, such as a benzylic, allylic or alkyl halide, an electron-poor arene, or a cyclic epoxide, to provide the corresponding sulfone products in good to excellent yields. The mild reaction conditions and use of commercially available reaction components allows the easy preparation of a broad range of sulfones featuring a variety of functional groups. The process obviates the need to employ thiol starting materials, and oxidative operations.

A palladium-catalyzed three-component coupling of arylboronic acids, sulfur dioxide and hydrazines

A novel and efficient route to aryl N-aminosulfonamides via a palladium-catalyzed three-component coupling of arylboronic acids, sulfur dioxide and hydrazines in the presence of a balloon of dioxygen is reported. The reaction proceeded smoothly under mild conditions and DABCO·(SO 2)2 was used as the source of sulfur dioxide.