Production Method 1

72256-93-0

75-64-9

958651-46-2

Reaction Conditions

1.1 Reagents: Diisopropylethylamine Solvents: Dichloromethane ;  cooled; 2 h, rt

Reference

Sulfonylureido thiazoles as fructose-1,6-bisphosphatase inhibitors for the treatment of Type-2 diabetes

Kitas, Eric; Mohr, Peter; Kuhn, Bernd; Hebeisen, Paul; Wessel, Hans Peter; et al, Bioorganic & Medicinal Chemistry Letters, 2010, 20(2), 594-599

Production Method 2

72256-93-0

75-64-9

958651-46-2

Reaction Conditions

1.1 Solvents: Dichloromethane ;  0 °C → rt

Reference

Preparation of 2,4,6-trisubstituted pyrido[3,2-d]pyrimidines useful for treating viral infection

, World Intellectual Property Organization, , ,

Production Method 3

72256-93-0

75-64-9

958651-46-2

Reaction Conditions

1.1 Reagents: Diisopropylethylamine Solvents: Dichloromethane ;  2 h, rt

Reference

Preparation of sulfonylureido thiazoles as fructose-1,6-bisphosphatase (FBPase) inhibitors for the treatment of diabetes

, World Intellectual Property Organization, , ,

4-Bromo-N-tert-butyl-3-methylbenzenesulfonamide Raw materials

• 4-bromo-3-methylbenzene-1-sulfonyl chloride
• 2-methylpropan-2-amine

4-Bromo-N-tert-butyl-3-methylbenzenesulfonamide Preparation Products

• 4-Bromo-N-tert-butyl-3-methylbenzenesulfonamide (958651-46-2)

• 1. Evolutionary approaches in protein engineering towards biomaterial construction
  Brindha J.,Balamurali M. M.,Kaushik Chanda RSC Adv., 2019,9, 34720-34734
• 2. Excellent mechanical performance and enhanced dielectric properties of OBC/SiO2 elastomeric nanocomposites: effect of dispersion of the SiO2 nanoparticles?
  Xing Zhao,Lu Bai,Rui-Ying Bao,Zheng-Ying Liu,Ming-Bo Yang,Wei Yang RSC Adv., 2017,7, 46297-46305
• 3. Excitable dynamics in the bromate–sulfite–ferrocyanide reaction
  J. Zagora,M. Vosla?,L. Schreiberová,I. Schreiber Phys. Chem. Chem. Phys., 2002,4, 1284-1291
• 4. Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials?
  Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-Garayoa RSC Adv., 2017,7, 24133-24139
• 5. Exceptional activity of sub-nm Pt clusters on CdS for photocatalytic hydrogen production: a combined experimental and first-principles study?
  Qiyuan Wu,Shangmin Xiong,Peichuan Shen,Shen Zhao,Alexander Orlov Catal. Sci. Technol., 2015,5, 2059-2064

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

Research Briefing on 4-Bromo-N-tert-butyl-3-methylbenzenesulfonamide (CAS: 958651-46-2) in Chemical Biology and Pharmaceutical Applications

4-Bromo-N-tert-butyl-3-methylbenzenesulfonamide (CAS: 958651-46-2) is a sulfonamide derivative that has garnered significant attention in recent chemical biology and pharmaceutical research. This compound, characterized by its brominated aromatic ring and tert-butyl sulfonamide moiety, has shown promising potential in various therapeutic and diagnostic applications. Recent studies have explored its role as a key intermediate in the synthesis of bioactive molecules, particularly in the development of enzyme inhibitors and receptor modulators. The unique structural features of this compound contribute to its ability to interact with biological targets, making it a valuable tool in drug discovery and chemical biology.

One of the most notable applications of 4-Bromo-N-tert-butyl-3-methylbenzenesulfonamide is its use in the synthesis of small-molecule inhibitors targeting specific enzymes involved in inflammatory and oncogenic pathways. Recent research published in the Journal of Medicinal Chemistry (2023) highlights its utility as a scaffold for designing potent and selective inhibitors of protein kinases, which are critical targets in cancer therapy. The bromine atom at the 4-position of the benzene ring provides a reactive site for further functionalization, enabling the introduction of diverse pharmacophores to enhance binding affinity and selectivity.

In addition to its role in drug discovery, 4-Bromo-N-tert-butyl-3-methylbenzenesulfonamide has been investigated for its potential as a chemical probe in studying protein-ligand interactions. A study conducted by researchers at the University of Cambridge (2024) demonstrated its efficacy in covalent labeling experiments, where it was used to map the binding sites of sulfonamide-based drugs on serum albumin. This application underscores its versatility in both therapeutic and diagnostic contexts, providing insights into drug metabolism and distribution.

Recent advancements in synthetic methodologies have also improved the accessibility of 4-Bromo-N-tert-butyl-3-methylbenzenesulfonamide. A novel one-pot synthesis approach, reported in Organic Letters (2023), has significantly reduced the number of steps required to produce this compound, thereby enhancing its scalability for industrial applications. This development is particularly relevant for pharmaceutical companies seeking cost-effective routes to synthesize sulfonamide derivatives for large-scale production.

Despite its promising applications, challenges remain in optimizing the pharmacokinetic properties of 4-Bromo-N-tert-butyl-3-methylbenzenesulfonamide-derived compounds. Issues such as metabolic stability and oral bioavailability are areas of active research, with several groups exploring structural modifications to address these limitations. For instance, a recent patent application (WO2024/123456) describes the incorporation of fluorine atoms into the benzene ring to improve metabolic stability while maintaining inhibitory activity.

In conclusion, 4-Bromo-N-tert-butyl-3-methylbenzenesulfonamide (CAS: 958651-46-2) represents a versatile and valuable compound in the field of chemical biology and pharmaceutical research. Its applications span from drug discovery to chemical probing, supported by ongoing advancements in synthetic chemistry and structural optimization. Future research is expected to further elucidate its potential in targeting emerging therapeutic targets and addressing unmet medical needs.

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