• 1. Feasible energy level tuning in polymer solar cells based on broad band-gap polytriphenylamine derivatives
  Bin Zhang,Guiting Chen,Jin Xu,Liwen Hu,Wei Yang New J. Chem. 2016 40 402
• 2. Regioselective β-silylation of porphyrins via iridium-catalyzed C–H bond activation
  Noriaki Sugita,Satoshi Hayashi,Masashi Shibata,Taiga Endo,Masahiro Noji,Kazuhiko Takatori,Toshikatsu Takanami Org. Biomol. Chem. 2016 14 10189
• 3. Transition-metal-free cross-coupling of thioethers with aryl(cyano)iodonium triflates: a facile and efficient method for the one-pot synthesis of thiocyanates
  Dan Zhu,Denghu Chang,Lei Shi Chem. Commun. 2015 51 7180
• 4. The use of carboxylic acids as traceless directing groups for regioselective C–H bond functionalisation
  Marc Font,Jacob M. Quibell,Gregory J. P. Perry,Igor Larrosa Chem. Commun. 2017 53 5584
• 5. Traceless directing groups: a novel strategy in regiodivergent C–H functionalization
  Geetika Rani,Vijay Luxami,Kamaldeep Paul Chem. Commun. 2020 56 12479

• Solvents and Organic Chemicals Organic Compounds Organic Halides

1-Iodo-3,5-bis(trifluoromethyl)benzene (CAS No. 328-73-4): A Versatile Building Block in Modern Chemical Research

In the realm of organic synthesis and materials science, 1-Iodo-3,5-bis(trifluoromethyl)benzene (CAS No. 328-73-4) has emerged as a critical intermediate due to its unique structural features and reactivity profiles. This compound, characterized by its iodine atom at the para position and two trifluoromethyl groups on the meta positions, exhibits exceptional versatility in both academic research and industrial applications. Recent advancements in cross-coupling chemistry and fluorine-containing materials have further solidified its role as a cornerstone for designing novel pharmaceuticals, optoelectronic devices, and advanced polymers.

The trifluoromethyl groups (C(CF?)?) confer significant electron-withdrawing effects and lipophilicity to the aromatic ring, enhancing stability against oxidation while modulating biological activity. These properties make 1-Iodo-3,5-bis(trifluoromethyl)benzene an ideal substrate for palladium-catalyzed Suzuki-Miyaura reactions. A 2023 study published in Journal of the American Chemical Society demonstrated its use in synthesizing biaryl scaffolds with high regioselectivity for antiviral drug candidates targeting RNA-dependent RNA polymerases. The iodine moiety (I-) serves as a reactive handle for C–C bond formation under mild conditions, enabling precise functionalization without compromising the trifluoromethyl groups.

In photovoltaic research, this compound has been leveraged to construct conjugated polymers with tailored electronic properties. A collaborative effort between MIT and Max Planck Institute revealed that incorporating 1-Iodo-3,5-bis(trifluoromethyl)benzene-derived units into polymer backbones improves charge carrier mobility by up to 40% compared to non-fluorinated analogs. The trifluoromethyl substituents reduce interchain π-stacking interactions while maintaining planarity of the conjugated system—a breakthrough highlighted in Nature Energy (2024).

Beyond material science applications, this compound's role in medicinal chemistry is expanding rapidly. Researchers at Stanford University recently utilized it as a key intermediate in synthesizing novel kinase inhibitors for cancer therapy. The trifluoromethyl groups enhance metabolic stability by resisting cytochrome P450 oxidation pathways, while the iodo group allows site-specific attachment of bioactive warhead molecules via Sonogashira coupling reactions.

Recent computational studies using density functional theory (DFT) have elucidated novel reaction pathways involving CAS No. 328-73-4. A team from ETH Zurich demonstrated that under ultrasonic irradiation conditions, this compound undergoes unexpected intramolecular Friedel-Crafts-type cyclization when treated with Lewis acids like BF?·OEt?. This discovery opens new avenues for one-pot synthesis of polycyclic fluorinated heterocycles—structures highly sought after in agrochemical development.

In industrial settings, continuous-flow synthesis methods have optimized production processes for 1-Iodo-3,5-bis(trifluoromethyl)benzene. A 2024 report from Angewandte Chemie detailed a microreactor-based approach achieving >95% yield with reduced solvent usage compared to traditional batch processes. This advancement aligns with current industry trends toward greener chemical manufacturing practices while maintaining product purity standards required for pharmaceutical intermediates.

The compound's spectroscopic signatures also contribute to analytical chemistry innovations. Researchers at NIST recently validated its NMR and IR spectra as reference standards for identifying fluorinated aromatic compounds in complex mixtures—a critical tool for quality control in pharmaceutical production lines adhering to FDA guidelines.

In summary, 1-Iodo-3,5-bis(trifluoromethyl)benzene (CAS No. 328-73-4) continues to redefine boundaries across multiple disciplines through its unique combination of structural features and reactivity profiles. Its presence in cutting-edge research—from CRISPR-based gene editing tools requiring fluorinated linkers to next-generation perovskite solar cells—underscores its indispensable role in advancing modern science and technology.

• 401-81-0(3-Iodobenzotrifluoride)
• 518343-63-0(1,4-diiodo-2-(trifluoromethyl)benzene)
• 455-13-0(4-Iodobenzotrifluoride)
• 214400-67-6(1,3-diiodo-5-(trifluoromethyl)benzene)
• 13055-62-4(2-Iodo-1-methyl-4-(trifluoromethyl)benzene)
• 54978-36-8(1-iodo-2-methyl-4-(trifluoromethyl)Benzene)
• 328-92-7(2-iodo-1,4-bis(trifluoromethyl)benzene)
• 65537-83-9(BENZENE, 5-IODO-1,2,3-TRIS(TRIFLUOROMETHYL)-)
• 862265-35-8(BENZENE, 1,4-DIIODO-2,5-BIS(TRIFLUOROMETHYL)-)
• 130656-70-1(1,2-Diiodo-4-(trifluoromethyl)benzene)