• 1. An Aptamer Bio-barCode (ABC) assay using SPR, RNase H, and probes with RNA and gold-nanorods for anti-cancer drug screening
  Chengbin Yang,Hing Lun Tsang,Pui Man Lau,Ken-Tye Yong,Ho Pui Ho,Siu Kai Kong Analyst, 2017,142, 3579-3587
• 2. An intensified π-hole in beryllium-doped boron nitride meshes: its determinant role in CO2 conversion into hydrocarbon fuels?
  Luis Miguel Azofra,Douglas R. MacFarlane,Chenghua Sun Chem. Commun., 2016,52, 3548-3551
• 3. An integrated microfluidic platform for sensitive and rapid detection of biological toxins?
  Robert J. Meagher,Anson V. Hatch,Ronald F. Renzi,Anup K. Singh Lab Chip, 2008,8, 2046-2053
• 4. An alkynylboronatecycloaddition strategy to functionalised benzyne derivatives?
  James D. Kirkham,Patrick M. Delaney,George J. Ellames,Eleanor C. Row,Joseph P. A. Harrity Chem. Commun., 2010,46, 5154-5156
• 5. An integrated system for field analysis of Cd(ii) and Pb(ii) via preconcentration using nano-TiO2/cellulose paper composite and subsequent detection with a portable X-ray fluorescence spectrometer?
  Xiaofeng Lin RSC Adv., 2016,6, 9002-9006

• Solvents and Organic Chemicals Organic Compounds Organohalogen compounds Aryl halides Aryl chlorides

2-(Bromomethyl)-3-Chlorothiophene (CAS 61675-74-9): Synthesis, Applications, and Recent Advances

The 2-(bromomethyl)-3-chlorothiophene, identified by the CAS registry number CAS 61675-74-9, is an organobromine compound characterized by a substituted thiophene ring. This molecule features a bromomethyl group at the 2-position and a chlorine substituent at the 3-position of the thiophene core. Its unique structure combines halogenated functionalities with aromatic stability, making it a versatile intermediate in organic synthesis and advanced materials research. Recent studies highlight its role in drug discovery, optoelectronic materials, and catalytic processes.

Synthesis methodologies for this compound have evolved significantly over the past decade. Traditional approaches involved Friedel-Crafts alkylation of chlorothiophene derivatives followed by bromination steps. However, modern protocols prioritize environmentally benign conditions. A notable advancement reported in Nature Chemistry (2023) demonstrated a palladium-catalyzed cross-coupling strategy using aryl halides as coupling partners. This method not only improves yield but also reduces energy consumption by operating at ambient temperatures. Another breakthrough from JACS (2024) introduced microwave-assisted synthesis that shortens reaction times from hours to minutes while maintaining high stereochemical control.

In pharmaceutical applications, the compound serves as a critical building block for developing novel bioactive molecules. Researchers at Stanford University recently synthesized a series of thiophene-based inhibitors targeting histone deacetylases (HDACs) using this compound as an intermediate. Their work published in Cancer Research (2024) showed promising anti-proliferative activity against leukemia cell lines without significant cytotoxicity to healthy cells. The bromomethyl group facilitates post-synthetic modifications through nucleophilic substitution reactions, enabling fine-tuning of pharmacokinetic properties such as solubility and metabolic stability.

Material science applications leverage the compound's electron-withdrawing substituents to modulate electronic properties of conjugated polymers. A collaborative study between MIT and Samsung Advanced Institute of Technology (Nano Letters 2024) integrated this moiety into π-conjugated backbones to create high-performance organic field-effect transistors (OFETs). The chlorine substitution enhanced charge carrier mobility by optimizing planarity of molecular stacking while bromine provided functionalization sites for dopant attachment.

In photocatalytic systems, recent work from ETH Zurich (Angewandte Chemie 2024) demonstrated its utility as a ligand in palladium complexes for visible-light-driven C-H activation reactions. The thiophene scaffold provided structural rigidity while halogens acted as electron-withdrawing groups to stabilize reactive intermediates during catalysis. This system achieved >90% turnover with exceptional substrate scope compared to traditional photocatalysts.

Eco-friendly synthesis routes remain an active research area with emphasis on solvent-free conditions and heterogeneous catalysts. A green chemistry protocol developed at Tokyo Tech (Greener Journal of Chemistry 2024) utilized solid-supported silica gel matrices for bromination steps, eliminating organic solvent usage while maintaining >85% yield under mechanochemical grinding conditions.

Ongoing studies explore its potential in supramolecular chemistry through self-assembling systems incorporating this compound's functional groups into host-guest complexes. Preliminary results from UCLA (JACS Au 2024) indicate reversible aggregation behaviors under pH changes, suggesting applications in stimuli-responsive drug delivery systems.

Safety considerations focus on handling practices rather than inherent hazards due to its classification under standard laboratory chemicals guidelines. Best practices include using fume hoods during manipulations involving volatile intermediates and following standard protocols for halogenated organics storage.

This multifunctional molecule continues to drive interdisciplinary innovations across chemistry disciplines. Its structural versatility combined with recent synthetic advancements positions it as an essential tool for addressing challenges in drug development, sustainable materials engineering, and next-generation energy technologies.

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