• 1. Synthesis of novel N-9 substituted 6-(4-(4-propoxyphenyl)piperazin-1-yl)-9H-purine derivatives as inducers of apoptosis in MCF-7 breast cancer cells
  Manjunath G. Sunagar,Supreet Gaonkar,Santosh G. Sunagar,Narahari Deshapande,Ningaraddi S. Belavagi,Imtiyaz Ahmed M. Khazi RSC Adv. 2016 6 15286

• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Ketones
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Ketones

Exploring the Synthesis and Applications of 2-Bromo-1-[4-(Trifluoromethoxy)phenyl]Ethan-1-One (CAS No. 103962-10-3)

The compound 2-bromo-1-[4-(trifluoromethoxy)phenyl]ethan-1-one, identified by CAS Registry Number CAS No. 103962-10-3, represents a structurally unique organobromine-containing aryl ketone with significant potential in pharmaceutical and synthetic chemistry applications. Its molecular architecture combines a bromine atom at the ethanone α-position, a trifluoromethoxy-substituted phenyl ring, and a ketone functional group, creating a versatile scaffold for further derivatization. Recent advancements in synthetic methodologies have enabled precise control over its synthesis, particularly through optimized transition-metal-catalyzed cross-coupling strategies reported in Angewandte Chemie International Edition (2023).

A critical feature of this compound lies in its trifluoromethoxy (p-TfO) substituent, which imparts enhanced metabolic stability and lipophilicity compared to unsubstituted analogs. Researchers at Stanford University demonstrated in a 2024 study that the trifluoromethoxy group significantly improves blood-brain barrier permeability when incorporated into CNS drug candidates, making this compound an ideal precursor for neuroactive agent development. The bromine atom further facilitates late-stage functionalization via nucleophilic aromatic substitution pathways, as evidenced by its successful use in Suzuki-Miyaura cross-couplings reported in Nature Chemistry.

In medicinal chemistry contexts, this compound serves as a privileged scaffold for developing kinase inhibitors targeting cancer pathways. A 2024 collaborative study between Genentech and MIT revealed that derivatives synthesized from this core exhibited sub-nanomolar IC?? values against mutant EGFR tyrosine kinases, outperforming clinically used osimertinib in cellular assays under hypoxic conditions mimicking tumor microenvironments. The ketone functionality allows for bioisosteric replacements with imine or oxime groups to modulate pharmacokinetic properties without sacrificing binding affinity.

Synthetic chemists have recently leveraged its structure to create novel macrocyclic frameworks through intramolecular Ullmann-type coupling reactions under microwave-assisted conditions (reported in JACS Au, 2023). This approach enabled the formation of rigid bicyclic systems with unprecedented conformational constraints, demonstrating utility in peptide mimetic design for GPCR modulation studies at Harvard Medical School's Drug Discovery Center.

Economic analysis from Frost & Sullivan's 2024 market report highlights growing demand for this compound as an intermediate in fluorinated drug development pipelines, with projected annual growth exceeding 8% through 2030 driven by oncology and neurology therapeutic areas. Its commercial availability from specialty chemical manufacturers now includes kilogram-scale production under cGMP conditions compliant with ICH Q7 guidelines.

Ongoing research focuses on stereoselective synthesis using chiral Br?nsted acid catalysts to access enantiopure forms for chiral ligand applications in asymmetric hydrogenation processes (highlighted in Nature Catalysis, 2024). Computational studies using DFT modeling have identified key steric interactions between the trifluoromethoxy group and transition metal centers that could revolutionize catalyst design strategies.

This compound's multifaceted utility stems from its balanced combination of functional groups offering orthogonal reactivity sites while maintaining structural stability during multi-step syntheses. Recent advances have validated its role as both a standalone therapeutic entity candidate and an indispensable building block across diverse chemical disciplines, cementing its position at the forefront of modern medicinal chemistry innovation.

• 887575-25-9(Ethanone,1-[4-[4-(trifluoromethoxy)phenoxy]phenyl]-)
• 651054-55-6(Methanone, (4-hydroxyphenyl)[4-(trifluoromethoxy)phenyl]-)
• 141134-24-9(2-Bromo-1-(4-(difluoromethoxy)phenyl)ethanone)
• 405921-09-7(2-Bromo-1-(2-(difluoromethoxy)phenyl)ethanone)
• 887575-19-1(Ethanone,1-[4-[3-(trifluoromethoxy)phenoxy]phenyl]-)
• 170141-63-6(3'-(Trifluoromethoxy)acetophenone)
• 85013-98-5(4'-(Trifluoromethoxy)acetophenone)
• 443914-96-3(3-(Difluoromethoxy)phenacyl bromide)
• 530141-40-3(2-(Trifluoromethoxy)phenacyl bromide)
• 237386-01-5(2-Bromo-3'-trifluoromethoxyacetophenone)