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CAS Number 142946-80-3

Chemistry Building Blocks, Fluorinated Building Blocks, Heterocyclic Building Blocks, Monomers

Product Code B1451-1g
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An electron withdrawing bipyridyl ligand

Used as a chelating ligand for the preparation of Ir(III) photocatalysts

5,5′-Bis(trifluoromethyl)-2,2′-bipyridine (5,5′-dCF3bpy), CAS number 142946-80-3, is a bipyridyl ligand with two electron withdrawing trifluoromethyl groups at 5,5'-positions on the conjugated bipyridyl rings. It is normally used as a chelating ligand for the preparation of the well-established [Ir(dFCF3ppy)2 (5,5′-dCF3bpy)]PF6 and other Ir(III) photocatalysts. [Ir(dFCF3ppy)2-(5,5′-dCF3bpy)]PF6 is a cyclometalated iridium(III) complex that are widely used in visible-light mediated photocatalytic organic transformations including the alkylation of remote C-H bonds and alkene aminoarylation.

Yellow light emitting cyclometalated iridium(III) complexes coordinated with ligand 5,5′-bis(trifluoromethyl)-2,2′-bipyridine, [Ir(Hppy)2(dCF3bpy)]PF6 and [Ir(HF2ppy)2(dCF3bpy)]PF6, show relative long lifetimes at room temperature owing to the phosphorescence derived from the mixed metal-ligand-to-ligand charge transfer (MLLCT) excited states. The system engaging the photosensitizers, K2PtCl4, and triethylamine showed highly efficient H2 evolution activities. The turnover numbers (TONs) of H2 evolution based on [Ir(Hppy)2(dCF3bpy)]PF6 and [Ir(HF2ppy)2(dCF3bpy)]PF6 at 96 h of irradiation were reached at 758 and 832 TONs, respectively.

Multiple functional groups

Multiple functional groups

For facile synthesis

Fluorinated building block

Fluorinated bipyridine building block

For semiconductors, dyes, and solar cells

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High purity 142946-80-3

High purity

>98% High purity

General Information

CAS Number 142946-80-3
Chemical Formula C12H6F6N2
Full Name 5,5'-Bis(trifluoromethyl)-2,2'-bipyridine
Molecular Weight 292.18 g/mol
Synonyms 5,5′-dCF3bpy, 5,5'-BTFMB, 5,5'-Bis(trifluoromethyl)-2,2'-bipyridyl
Classification / Family Bipyridyl derivatives, Heterocyclic building blocks, Semiconductor synthesis intermediates, Dye-sensitized solar cells (DSSCs)

Chemical Structure

5,5'-Bis(trifluoromethyl)-2,2'-bipyridine chemical structure, 142946-80-3
5,5'-Bis(trifluoromethyl)-2,2'-bipyridine (5,5′-dCF3bpy), CAS 142946-80-3

Product Details

Purity >98% (1H NMR)
Melting Point 131 °C
Appearance White to off-white powder/crystals

MSDS Documentation

5,5'-Bis(trifluoromethyl)-2,2'-bipyridine5,5'-Bis(trifluoromethyl)-2,2'-bipyridine MSDS Sheet

Literature and Reviews

  1. Photophysical properties and photosensitizing abilities for hydrogen evolution reactions of robust cyclometalated iridium(III) complexes with 5,5′-bis(trifluoromethyl)-2,2′-bipyridine, N. Yano et al., J. Photochem. Photobiol. A: Chem., 400, 112716 (2020); 10.1016/j.jphotochem.2020.112716.
  2. Modified Ullmann coupling of 2-chloro-3-trifluoromethylpyridine, S. Munavalli et al., J. Fluor. Chem., 73 (1), 1-6 (1995); DOI: 10.1016/0022-1139(94)03168-Y.
  3. Trifluoromethyl-substituted 2,2'-bipyridine ligands. Synthetic control of excited-state properties of ruthenium(II) tris-chelate complexes, M. Furue at al., Inorg. Chem., 31 (18), 3792–3795 (1992); DOI: 10.1021/ic00044a022.
  4. Broad-Spectrum Catalysts for the Ambient Temperature Anti-Markovnikov Hydration of Alkynes, L. Li et al., Angew. Chem., 126 (30), 8026-8029 (2014); DOI: 10.1002/ange.201404320.
  5. Catalytic alkylation of remote C–H bonds enabled by proton-coupled electron transfer, G. Choi et al., Nature, 539, 268–271 (2016); DOI: 10.1038/nature19811.
    Site-Selective Alkoxylation of Benzylic C–H Bonds via Photoredox Catalysis, B. Lee et al., Angew. Chem. Int. Ed., 59(1), 197–202 (2020); DOI: 10.1002/anie.201910602.
  6. Thioamidate Ion as Effective Cocatalyst for Photoinduced C–H Alkylation via Multisite Proton-coupled Electron Transfer, K. Ohmatsu et al., Chem. Lett., 51 (4), 445-447 (2022); DOI: 10.1246/cl.220026.
  7. Cooperative photoredox and chiral hydrogen-bonding catalysis, Y. Yin et al., Org. Chem. Front., 7, 1283-1296 (2020); DOI: 10.1039/D0QO00276C.

To the best of our knowledge the information provided here is accurate. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. Products may have minor cosmetic differences (e.g. to the branding) compared to the photos on our website. All products are for laboratory and research and development use only.

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