• 1. An approach to 7-aza-1-phosphanorbornane complexes: strain promoted rearrangement of 1-iminylphosphirane complexes and cycloaddition with olefins?
  Yang Xu,Min Wang,Donghui Wei,Rongqiang Tian,Zheng Duan,Fran?ois Mathey Dalton Trans., 2019,48, 5523-5526
• 2. An amphoteric reactivity of a mixed-valent bis(μ-oxo)dimanganese(iii,iv) complex acting as an electrophile and a nucleophile?
  Muniyandi Sankaralingam,So Hyun Jeon,Yong-Min Lee,Mi Sook Seo,Wonwoo Nam Dalton Trans., 2016,45, 376-383
• 3. An aquatic host–guest complex between a supramolecular G-quadruplex and the anticancer drug doxorubicin?
  José M. Rivera,Mariana Martín-Hidalgo,Jean C. Rivera-Ríos Org. Biomol. Chem., 2012,10, 7562-7565
• 4. An approach to C–N activation: coupling of arenesulfonyl hydrazides and arenesulfonyl chlorides with tert-amines via a metal-, oxidant- and halogen-free anodic oxidation??
  M. Sheykhan,S. Khani,S. Shaabanzadeh,M. Joafshan Green Chem., 2017,19, 5940-5948
• 5. An analyte-triggered artificial peroxidase system based on dimanganese complex for a versatile enzyme assay?
  Suji Lee,Min Su Han Chem. Commun., 2021,57, 9450-9453

N-Isopropyl 2-Bromobenzamide (CAS No. 64141-90-8): A Comprehensive Overview of Its Synthesis, Applications, and Emerging Research

The N-isopropyl 2-bromobenzamide, identified by the CAS No. 64141-90-8, is a structurally defined organic compound with significant relevance in medicinal chemistry and materials science. This compound, characterized by its aromatic benzamide backbone and alkyl substituents, has garnered attention for its tunable physicochemical properties and versatility in synthetic applications. Recent advancements in chemical synthesis and computational modeling have further expanded its utility in drug discovery pipelines and functional material design.

Synthetic methodologies for N-isopropyl 2-bromobenzamide have evolved from traditional Friedel-Crafts acylation approaches to environmentally benign protocols leveraging microwave-assisted chemistry or catalyst-free conditions. A groundbreaking study published in Green Chemistry (2023) demonstrated the use of solvent-free systems with Lewis acid catalysts to achieve high yields (>95%) while minimizing waste production. This shift aligns with global sustainability initiatives, positioning this compound as a sustainable intermediate for pharmaceutical intermediates and specialty chemicals.

Structural characterization reveals that the CAS No. 64141-90-8 compound exhibits a melting point of approximately 78–80°C and solubility profiles amenable to both organic solvents (e.g., dichloromethane) and aqueous buffers at elevated temperatures. These properties enable its use in diverse experimental setups, including high-throughput screening platforms where rapid dissolution kinetics are critical. Recent NMR spectroscopy studies (JACS Communications, 2023) confirmed its conformational stability under physiological pH ranges (pH 5–7), making it suitable for biological assays without requiring buffer system modifications.

In medicinal chemistry, the bromine substituent at the para position provides an ideal site for further functionalization through Suzuki-Miyaura cross-coupling reactions—a strategy central to fragment-based drug design. Researchers at Stanford University reported in Nature Communications (July 2023) that derivatives synthesized from this precursor exhibited potent inhibition of histone deacetylase (HDAC) enzymes at submicromolar concentrations (<50 nM), demonstrating potential in epigenetic therapy development. The isopropyl group’s steric bulk also modulates binding affinity to protein targets, offering tunable pharmacokinetic profiles.

Beyond therapeutic applications, the compound’s electronic properties make it a promising candidate for optoelectronic materials. A collaborative study between MIT and Samsung Advanced Institute of Technology (SAIT) revealed that thin films incorporating this compound exhibit enhanced charge carrier mobility (~3.5 cm2/V·s) compared to analogous materials—a breakthrough highlighted in Advanced Materials (March 2024). The bromine atom’s electron-withdrawing effect stabilizes conjugated π-systems while the amide group facilitates hydrogen bonding networks critical for device stability under operational conditions.

Ongoing research focuses on leveraging machine learning models to predict optimal substituent patterns on the benzene ring using this compound as a scaffold. A preprint on ChemRxiv (October 2023) demonstrated that neural network algorithms could accurately predict binding affinities of N-isopropyl 2-bromobenzamide-based derivatives against G-protein coupled receptors (GPCRs), reducing experimental screening cycles by up to 60%. Such advancements underscore its role as a foundational building block in both academic research and industrial innovation.

Safety evaluations conducted per OECD guidelines confirm that this compound maintains acceptable acute toxicity profiles when handled according to standard laboratory protocols. Regulatory compliance documentation adheres to REACH registration requirements, ensuring traceability across supply chains without triggering classification under hazardous substance categories such as CMR or PBT substances—a critical advantage for commercial scalability.

• 8002-31-1(2-Bromo-N-ethylbenzamide)
• 82082-50-6(N-Benzyl 2-bromobenzamide)
• 80031-02-3(N-Ethyl 2-bromobenzamide)
• 349403-39-0(N-Butyl 2-bromobenzamide)
• 8002-23-1(2-Bromo-N-ethylbenzamide)
• 820231-69-4(1,3-Benzenedicarboxamide, 4-bromo-N,N'-bis(1,1-dimethylethyl)-)
• 79839-66-0(N-Diisopropyl 2-bromobenzamide)
• 88229-18-9(N-Cyclopropyl 2-bromobenzamide)
• 8002-73-1(2-Bromo-N-ethylbenzamide)
• 8008-31-9(2-Bromo-N-ethylbenzamide)