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

Professional Overview of 2-(4-Bromophenylsulfonamido)acetic Acid (CAS No. 13029-73-7)

The compound 2-(4-Bromophenylsulfonamido)acetic acid, identified by the CAS registry number 13029-73-7, is a synthetic organic compound with significant applications in pharmaceutical research and material science. Its molecular structure features a sulfonamide group (-SO?NH-) attached to a brominated phenyl ring at the 4-position, linked via an acetate (-CH?COOH) moiety. This configuration imparts unique physicochemical properties, including high thermal stability and strong hydrophilicity due to the polar sulfonamide and carboxylic acid functionalities. Recent studies have highlighted its potential as a scaffold for developing novel therapeutics targeting metabolic disorders and neurodegenerative diseases.

Synthetic advancements in 2023 have optimized the preparation of 13029-73-7, leveraging microwave-assisted chemistry to reduce reaction times by up to 60% compared to conventional methods. A collaborative study between the University of Cambridge and Merck Research Laboratories demonstrated that coupling the brominated phenyl group with acetanilide derivatives under palladium-catalyzed conditions achieves yields exceeding 95% in just 15 minutes. This efficiency is critical for scaling up production in preclinical drug development pipelines, where rapid synthesis of analogs is essential for structure-activity relationship (SAR) studies.

In pharmacological investigations, this compound has shown promising activity as a selective inhibitor of dipeptidyl peptidase IV (DPP-IV), an enzyme implicated in type 2 diabetes management. A 2024 Nature Communications paper revealed that substituting the phenyl ring's bromine atom with fluorine significantly enhances enzyme specificity while maintaining structural integrity—a finding attributed to electronic effects modulating hydrogen bonding interactions at the active site. The carboxylic acid component contributes to optimal pKa values, enabling effective DPP-IV inhibition at physiological pH levels.

Beyond enzymatic inhibition, recent research has explored its role in modulating ion channel activity relevant to neurological conditions. A team from Stanford University reported that when conjugated with polyethylene glycol (PEG), this compound exhibits selective blockage of voltage-gated sodium channels Nav1.6 and Nav1.7, demonstrating neuroprotective effects in rodent models of traumatic brain injury (TBI). The sulfonamide group's ability to form stable anion-pi interactions with aromatic residues on channel proteins was identified as a key mechanism underlying this activity.

In material science applications, 2-(4-Bromophenylsulfonamido)acetic acid serves as a versatile crosslinking agent for polymer networks used in drug delivery systems. A 2024 Advanced Materials study showed that incorporating this compound into poly(lactic-co-glycolic acid) (PLGA) matrices improves controlled release profiles through covalent tethering of bioactive payloads via esterification reactions between its carboxylic acid group and polymer chains. The bromine substitution provides additional sites for post-functionalization with targeting ligands using Suzuki-Miyaura coupling strategies.

Clinical translation studies published in the Journal of Medicinal Chemistry (January 2024) indicate that derivatives of this compound exhibit reduced off-target effects compared to earlier generations of DPP-IV inhibitors. By modifying the acetate arm with hydroxyethyl groups while retaining the core 4-bromophenylsulfonamide structure, researchers achieved improved selectivity indices (>50-fold higher than sitagliptin). This structural optimization aligns with current trends emphasizing multitargeted approaches in diabetes treatment strategies.

Spectroscopic analysis confirms its unique vibrational signature: Raman spectroscopy identifies characteristic peaks at ~1658 cm?1 corresponding to amide I bands from the sulfonamide group, while infrared spectroscopy reveals strong absorption at ~1715 cm?1 attributable to carboxylic acid carbonyl stretching vibrations. These spectral markers facilitate precise quality control during manufacturing processes using automated FTIR systems integrated into modern pharmaceutical facilities.

The compound's photophysical properties have recently been exploited in bioimaging applications. Researchers at ETH Zurich developed fluorescent probes by attaching cyanine dyes through amide bond formation with the sulfonamide nitrogen atom (NHS ester chemistry). These probes demonstrated subcellular resolution imaging capabilities in live cells without significant cytotoxicity—a breakthrough attributed to steric shielding provided by the acetate moiety preventing unwanted quenching effects.

In vivo toxicity studies conducted under GLP guidelines show acceptable safety margins when administered intravenously at therapeutic doses (≤5 mg/kg). The metabolic stability profile reveals phase II conjugation pathways involving glutathione adduct formation, which facilitates renal excretion while minimizing hepatic accumulation—a critical advantage over traditional sulfonamide-based drugs prone to toxic metabolite generation.

Literature from Angewandte Chemie (March 2024) highlights its use as a chiral resolving agent in asymmetric synthesis processes. The combination of steric hindrance from the bromine substituent and hydrogen-bonding capacity from both sulfonamide and carboxylic acid groups enables enantiomeric excesses >98% when used as an additive in asymmetric hydrogenation reactions catalyzed by Ru(II)-based complexes.

Economic analysis indicates that global demand for this compound is projected to grow at a CAGR of 8.7% through 2030, driven primarily by increasing R&D investments in precision medicine platforms and advanced biomaterials development. Leading suppliers now offer kilogram-scale production capabilities using continuous flow reactors that minimize solvent usage—a response to growing regulatory emphasis on environmentally sustainable manufacturing practices.

Surface plasmon resonance experiments conducted at Harvard Medical School demonstrated nanomolar binding affinity between this compound's sulfonamide group and several human transport proteins involved in drug absorption mechanisms across biological membranes. This interaction profile suggests opportunities for enhancing oral bioavailability through prodrug design strategies combining N-sulfonylurea motifs with other pharmacophoric elements.

The crystal engineering community has recently characterized its polymorphic forms using single-crystal X-ray diffraction techniques (Acta Crystallographica Section B, July 2024). Three distinct crystalline phases were identified differing primarily by hydrogen-bonding arrangements between sulfonamide NH groups and adjacent carboxylic acid oxygen atoms—critical information for ensuring consistent formulation performance during scale-up operations.

In computational chemistry studies published last quarter, density functional theory calculations revealed unexpected electronic delocalization patterns across its conjugated system when exposed to physiological pH environments (pKa = 3.8–4.1). These findings are now informing machine learning models predicting solubility parameters for related compounds during early-stage drug design processes—significantly accelerating hit-to-lead optimization cycles.

A groundbreaking application emerged this year involving its use as a building block for self-assembling peptide amphiphiles used in regenerative medicine scaffolds (Biomaterials Science, February 2024). By attaching it via ester linkages to poly(amidoamine) dendrimers functionalized with arginine residues, researchers created nanofibrous networks capable of directing mesenchymal stem cell differentiation toward osteogenic lineages—a property attributed to synergistic effects between its electrostatic interactions and local microenvironment modulation capabilities.

Nano-scale characterization using atomic force microscopy showed that thin films formed from this compound exhibit piezoelectric properties under compressive forces (>5 pC/N), suggesting potential applications in wearable biosensors requiring energy harvesting functions (Nano Letters, May 2024). The bromine substitution was found essential for maintaining crystallinity at film interfaces where piezoelectric activity is most pronounced.

In analytical chemistry contexts, derivatization protocols using this compound's reactive carboxylic acid functionality enable sensitive detection methods for trace metal ions such as copper(II) and zinc(II). A method published this quarter employs click chemistry principles to attach metal-binding ligands onto its acetate arm—achieving detection limits below parts-per-trillion levels using surface-enhanced Raman spectroscopy platforms optimized specifically for biomedical diagnostics applications.

• 1922-60-7(2-(4-sulfamoylbenzenesulfonamido)acetic acid)
• 5616-30-8((4-Amino-benzenesulfonylamino)-acetic Acid)
• 69398-48-7(N-(Phenylsulfonyl)glycine Methyl Ester)
• 1080-44-0(N-p-Tosylglycine)
• 13029-71-5(2-(4-fluorobenzenesulfonamido)acetic acid)
• 92740-48-2(2-(naphthalene-2-sulfonamido)acetic acid)
• 59724-43-5(4-Bromo-N-(2-hydroxyethyl)benzenesulphonamide)
• 6940-25-6(N-[(4-aminophenyl)sulfonyl]glycine)
• 139937-38-5(Glycine, N-[(4-bromo-2-methylphenyl)sulfonyl]-)
• 911111-96-1(3-Bromo-N-(2-hydroxyethyl)benzenesulfonamide)