Production Method 1

873-55-2

90-10-8

Reaction Conditions

1.1 Reagents: Iodine ,  Oxygen Solvents: 1,2-Dichloroethane ;  16 h, 25 °C

Reference

Metal-Free Direct Construction of Sulfonamides via Iodine-Mediated Coupling Reaction of Sodium Sulfinates and Amines at Room Temperature

Wei, Wei; Liu, Chun Li; Yang, Daoshan; Wen, Jiangwei; You, Jinmao; et al, Advanced Synthesis & Catalysis, 2015, 357(5), 987-992

Production Method 2

591-50-4

5183-78-8

90-10-8

Reaction Conditions

1.1 Reagents: Durene ,  Tripotassium phosphate Catalysts: Cuprous iodide
1.2 Reagents: N1,N2-Dimethyl-1,2-cyclohexanediamine Solvents: 1,4-Dioxane ;  240 min, 110 °C

Reference

UFU (Ullmann-Finkelstein-Ullmann): a new multicomponent reaction

Toto, Patrick; Gesquiere, Jean-Claude; Cousaert, Nicolas; Deprez, Benoit; Willand, Nicolas, Tetrahedron Letters, 2006, 47(28), 4973-4978

Production Method 3

98-80-6

5183-78-8

90-10-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Cupric acetate Solvents: Water ;  5 h, reflux

Reference

Copper-catalyzed n-arylation of sulfonamides with boronic acids in water under ligand-free and aerobic conditions

Nasrollahzadeh, Mahmoud; Ehsani, Ali; Maham, Mehdi, Synlett, 2014, 25(4), 505-508

Production Method 4

90-10-8

Reaction Conditions

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  12 h, 25 °C

Reference

Towards Uniform Iodine Catalysis: Intramolecular C-H Amination of Arenes under Visible Light

Martinez, Claudio; Bosnidou, Alexandra E.; Allmendinger, Simon; Muniz, Kilian, Chemistry - A European Journal, 2016, 22(29), 9929-9932

Production Method 5

1678-25-7

90-10-8

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Acetone ;  1 h, reflux

Reference

Synthesis of a Series of 2-Aminodiarylsulfones by Bronsted Acid Mediated Regioselective Fries Type Rearrangement of N-Alkyl-N-arylbenzenesulfonamides

Debnath, Sudarshan; Mondal, Shovan, ChemistrySelect, 2018, 3(15), 4129-4132

Production Method 6

90-10-8

Reaction Conditions

1.1 Catalysts: Cadmium sulfide (nanoparticles) Solvents: Ethanol ,  Water ;  10 min, 25 - 28 °C

Reference

Nanosized CdS as a Reusable Photocatalyst: The Study of Different Reaction Pathways between Tertiary Amines and Aryl Sulfonyl Chlorides through Visible-Light-Induced N-Dealkylation and C-H Activation Processes

Firoozi, Somayeh; Hosseini-Sarvari, Mona, Journal of Organic Chemistry, 2021, 86(3), 2117-2134

Production Method 7

1678-25-7

90-10-8

Reaction Conditions

Reference

Preparation and spectroscopic behavior of acetyl derivatives of sulfonamides

Melegari, M.; Vampa, G.; Benedetti, L.; De Benedetti, P. G., Farmaco, 1976, 31(3), 183-93

Production Method 8

90-10-8

Reaction Conditions

1.1 Catalysts: Titania Solvents: Ethanol ;  1 h, rt

Reference

Black TiO2 nanoparticles with efficient photocatalytic activity under visible light at low temperature: regioselective C-N bond cleavage toward the synthesis of thioureas, sulfonamides, and propargylamines

Koohgard, Mehdi; Hosseini-Sarvari, Mona, Catalysis Science & Technology, 2020, 10(20), 6825-6839

Production Method 9

7025-95-8

90-10-8

Reaction Conditions

1.1 Reagents: Calcium hydride Solvents: Acetonitrile ;  5 min, 90 °C; 1 h, 90 °C

Reference

Charge-Transfer Complex Promoted Regiospecific C-N Bond Cleavage of Vicinal Tertiary Diamines

Fu, Ying; Xu, Qin-Shan; Shi, Chun-Zhao; Du, Zhengyin; Xiao, Caiqin, Advanced Synthesis & Catalysis, 2018, 360(18), 3502-3506

Production Method 10

5183-78-8

90-10-8

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: N,N-Dimethylglycine ,  Cuprous iodide Solvents: Dimethylformamide ;  48 h, 100 °C; 100 °C → rt

Reference

Copper-catalyzed cross-coupling of sulfonamides with aryl iodides and bromides facilitated by amino acid ligands

Deng, Wei; Liu, Lei; Zhang, Chen; Liu, Min; Guo, Qing-Xiang, Tetrahedron Letters, 2005, 46(43), 7295-7298

Production Method 11

90-10-8

Reaction Conditions

1.1 Reagents: Pyridine Solvents: Chloroform ;  0 °C; 30 min, 0 °C
1.2 0 °C; 2 - 4 h, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  neutralized, rt

Reference

Mechanistic insight into thermal 1,3- and 1,5-sulfonyl migrations of N-arenesulfonylphenothiazines and N-arenesulfonylphenoxazines

Wang, Jiandong; Son, Kwon-Il; Xu, Jiaxi, Monatshefte fuer Chemie, 2016, 147(9), 1637-1649

N-Methyl-N-phenylbenzenesulfonamide Raw materials

• Phenylboronic acid
• Iodobenzene
• N-methylbenzenesulfonamide
• Benzenesulfinic acid, sodium salt
• N-Phenylbenzenesulfonamide
• 1,2-Ethanediamine, N,N'-dimethyl-N,N'-diphenyl-

N-Methyl-N-phenylbenzenesulfonamide Preparation Products

• N-Methyl-N-phenylbenzenesulfonamide (90-10-8)

• 1. Excellent energy storage performance in NaNbO3-based relaxor antiferroeic ceramics under a low electric field
  XuxinCheng,XiaomingChen,PengyuanFan
• 2. Emergence of microfluidic wearable technologies
  Joo Chuan Yeo,Kenry Lab Chip, 2016,16, 4082-4090
• 3. Exchangeability of amino acid residues with similar physicochemical properties in coiled-coil interactions?
  Guiying Zhang,Maosheng Cheng,Yanni Li,Keliang Liu,Lifeng Cai Chem. Commun., 2013,49, 11086-11088
• 4. Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries?
  Zhiyan Chen,Nan Wu,Yaobing Wang,Bing Wang,Yingde Wang J. Mater. Chem. A, 2018,6, 516-526
• 5. Excellent lithium ion storage property of porous MnCo2O4 nanorods?
  Peiyuan Zeng,Xiaoxiao Wang,Ming Ye,Qiuyang Ma,Jianwen Li,Wanwan Wang,Baoyou Geng,Zhen Fang RSC Adv., 2016,6, 23074-23084

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Sulfanilides

Introduction to N-Methyl-N-phenylbenzenesulfonamide (CAS No. 90-10-8)

N-Methyl-N-phenylbenzenesulfonamide, with the chemical formula C₁₃H₁₃NO₂S and a CAS number of 90-10-8, is a significant compound in the field of organic chemistry and pharmaceutical research. This compound belongs to the class of sulfonamides, which are widely recognized for their diverse biological activities and applications in medicinal chemistry. The structural integrity of N-Methyl-N-phenylbenzenesulfonamide, featuring a benzene ring substituted with a sulfonyl group and amine functionalities, makes it a versatile intermediate in synthetic chemistry.

The synthesis of N-Methyl-N-phenylbenzenesulfonamide typically involves the reaction between methylamine and phenyl benzenesulfonyl chloride, followed by purification processes to achieve high yield and purity. This synthetic route is well-documented in the literature and has been optimized for industrial-scale production. The compound's stability under various conditions makes it suitable for further functionalization, enabling the development of more complex derivatives.

In recent years, N-Methyl-N-phenylbenzenesulfonamide has garnered attention due to its potential applications in drug discovery. Research has highlighted its role as a precursor in the synthesis of bioactive molecules targeting various therapeutic areas. For instance, sulfonamides have been extensively studied for their antimicrobial properties, and derivatives of N-Methyl-N-phenylbenzenesulfonamide have shown promising results in preliminary screenings.

One of the most intriguing aspects of N-Methyl-N-phenylbenzenesulfonamide is its ability to act as a scaffold for designing novel pharmacophores. The presence of both hydrophobic and hydrophilic regions in its structure allows for interactions with biological targets such as enzymes and receptors. This characteristic has led to investigations into its potential as an anti-inflammatory agent, with some studies suggesting that certain derivatives exhibit significant inhibitory activity against inflammatory cytokines.

The pharmaceutical industry has been particularly interested in exploring the therapeutic potential of sulfonamides due to their favorable pharmacokinetic properties. N-Methyl-N-phenylbenzenesulfonamide, being a structurally simple yet potent sulfonamide derivative, serves as an excellent starting point for developing new drugs. Researchers are currently investigating its efficacy in treating conditions such as autoimmune disorders and neurodegenerative diseases, where sulfonamides have demonstrated therapeutic promise.

Moreover, the compound's role in material science cannot be overlooked. The unique electronic properties of N-Methyl-N-phenylbenzenesulfonamide make it a candidate for use in organic semiconductors and conductive polymers. These materials are essential components in the development of flexible electronics and advanced sensors, where sulfonamides contribute to improved performance due to their electron-withdrawing capabilities.

The environmental impact of N-Methyl-N-phenylbenzenesulfonamide is another area of concern that warrants discussion. While the compound itself is not classified as hazardous, its derivatives may exhibit different environmental behaviors. Therefore, it is crucial to conduct thorough environmental risk assessments before large-scale applications are considered. Efforts are ongoing to develop greener synthetic routes that minimize waste and reduce environmental footprint.

In conclusion, N-Methyl-N-phenylbenzenesulfonamide (CAS No. 90-10-8) is a multifaceted compound with significant implications in pharmaceuticals, materials science, and environmental chemistry. Its structural features enable diverse applications, from drug development to advanced materials. As research continues to uncover new possibilities, this compound will undoubtedly remain a subject of interest for scientists and industry professionals alike.

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