A halogenated pyridine building block

As an intermediate for ligands and catalysts synthesis

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2-Bromo-4-fluoropyridine (CAS number 357927-50-5) is a dihalogenated pyridine with a bromine and a fluorine at 2- and 4-positions. 2,2'-Bipyridine ligands can be easily synthesized from 2-bromo-4-fluoropyridine reacting with bis(tributyltin) through Stille coupling. The fluoro substituents originated from 2-bromo-4-fluoropyridine enable the as synthesized 2,2'-bipyridine ligands for further functionalization. A Janus-type organoiridium complex is prepared with such method, bearing both hole- and electron-transporting moieties. 2-Bromo-4-fluoropyridine is also used to synthesize a bis(pyridine) ligands with 1,2-ethynylbenzene via Sonogashira coupling. The bis(pyridine) stabilizes iodine cation through [N−I−N] halogen bonding, for developing halogenating reagents.

A chemical catalyst is designed based on 2-bromo-4-fluoropyridine for site-selective lysine acylation of histones.

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Chemical Structure

Product Details

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Literature and Reviews

1. Highly phosphorescent cyclometalated iridium(III) complexes for optoelectronic applications: fine tuning of the emission wavelength through ancillary ligands, Ł. Skórka et al., J. Phys. Chem. C, 120(13), 7284–7294(2016); DOI: 10.1021/acs.jpcc.6b01663.
   
2. Janus-type dendritic organoiridium(III) complex bearing hole- and electron-transporting moieties: synthesis, luminescence properties, and OLED applications, N. Okamura et al., Bull. Chem. Soc. Jpn., 91, 1419–1428(2018), DOI: 10.1246/bcsj.20180139.
   
3. Kinetic analyses and structure-activity relationship studies of synthetic lysine acetylation catalysts, K. Yamatsugu et al., Bioorganic Med. Chem. Lett., 26(19), 5359–5367(2018); DOI: 10.1016/j.bmc.2018.07.009.