23484-62-0

Usage

Physical form

Bright yellow, crystalline solid

Solubility

Soluble in water

Toxicity

Highly toxic to humans, animals, and the environment

Use

Non-selective herbicide and pesticide widely used in agriculture

Regulation

Tightly regulated and use restricted in many countries

Health effects

Exposure can cause severe respiratory and organ damage, potentially fatal

Upstream product

• 366-18-7 [2,2]bipyridinyl 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 26437-49-0 tris(2-pyridyl)phosphine oxide 

Relevant academic research and scientific papers

A Novel Zeolite-Induced Population of a Planar Viologen Conformation. New Viologen Charge Transfer Complexes and Alkene/Viologen/Zeolite Arrays

A rare example of a novel zeolite-induced conformational change and a mechanism for this process are suggested in order to rationalize an unexpected spontaneous intrazeolite reduction observed during preparation of a new viologen (MQ2+)-doped zeolite (NaY). In addition, the formations of six new alkene/viologen/zeolite charge transfer (CT) arrays using NaMQY and the previously reported NaMVY are also reported. The binding constants between MQ2+ and MV2+ and 2,3-dimethyl-2-butene (TME) were determined using the Benesi-Hildebrand approach, and the stabilities of these CT complexes are compared to their intrazeolite analogue.

HPLC analysis of aliphatic sulfonate surfactants using ion-pair detection

A method was developed for the analysis of a number of surfactants which contained no UV-chromophores, using RP-HPLC with Indirect Photometric Detection, IPD. Pyridinium salts such as N-methylpyridinium iodide, N-methyl-2,2′- dipyridinium iodide and N,N′-dimethyl-2,2′-dipyridinium diiodide, were used as the visualization reagents, forming ion-pair complexes with the sulfonate surfactants. This allowed ordinary UV-detection. N-methylpyridinium iodide proved to be a suitable reagent, both with respect to ease of preparation and response. The eluents consisted of mixtures of acetonitrile and water, being 0.1 - 0.25 mM with respect to pyridinium salt. The method was sensitive and exhibited good signal to noise ratios, as well as linear responses over a wide concentration range. All of the analyzed surfactants were separated, including the diastereomeric forms of some of the surfactants.

Effect of chemical structure of bipyridinium salts as electron carrier on the visible-light induced conversion of CO2 to formic acid with the system consisting of water-soluble zinc porphyrin and formate dehydrogenase

Effect of chemical structures of some 2,2′-bipyridinium salts (BP2+) as the electron carrier molecules on the visible-light induced conversion of CO2 to formic acid with the system consisting of water-soluble zinc tetraphneylporphyrin tetrasulfonate (ZnTPPS) and formate dehydrogenase (FDH) in the presence of triethanolamine (TEOA) as an electron donor molecule was investigated. Irradiation of a CO2 saturated solution containing TEOA, ZnTPPS, BP2+ and FDH with visible light resulted in production of formic acid. By using 1,1′-ethylene-2,2′-bipyridinium dibromide (DB2+) as an electron carrier molecule, the effective formic acid production was observed compared with the other 2,2′-bipyridinium salt derivatives.

Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water

A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is

Synthesis of 2-Formylpyrroles from Pyridinium Iodide Salts

The first I2-mediated synthesis of 2-formylpyrroles from pyridinium salts is reported. This protocol enables the synthesis of diversely substituted 2-formylpyrroles in good yields under operationally simple conditions. The detailed mechanistic studies reveal that the reaction proceeds via a novel H2O-triggered ring opening of the pyridinium salt and a subsequent intramolecularly nucleophilic addition sequence.

Cyclometalated Ir(III) complexes of deprotonated N-methylbipyridinium ligands: Effects of quaternised N centre position on luminescence

Six new tricationic IrIII complexes of cyclometalating ligands derived from 1-methyl-2-(2′-pyridyl)pyridinium or 1-methyl-4-(2′-pyridyl)pyridinium are described. These complexes of the form [IrIII(C∧N)2(N∧N)]3+ (C∧N = cyclometalating ligand; N∧N = α-diimine) have been isolated and characterised as their PF6- and Cl- salts. Four of the PF6- salts have been studied by X-ray crystallography, and structures have been obtained also for two complex salts containing MeCN and Cl- or two Cl- ligands instead of N∧N. The influence of the position of the quaternised N atom in C∧N and the substituents on N∧N on the electronic/optical properties are compared with those of the analogous complexes where C∧N derives from 1-methyl-3-(2′-pyridyl)pyridinium (B. J. Coe, et al., Dalton Trans., 2015, 44, 15420). Voltammetric studies reveal one irreversible oxidation and multiple reduction processes which are mostly reversible. The new complexes show intramolecular charge-transfer absorptions between 350 and 450 nm, and exhibit bright green luminescence, with λmax values in the range 508-530 nm in both aqueous and acetonitrile solutions. In order to gain insights into the factors that govern the emission properties, density functional theory (DFT) and time-dependent DFT calculations have been carried out. The results confirm that the emission arises largely from triplet excited states of the C∧N ligand (3LC), with some triplet metal-to-ligand charge-transfer (3MLCT) contributions.

Regioselective functionalization of 2,2′-bipyridine and transformations into unsymmetric ligands for coordination chemistry

Novel synthetic strategies for a series of unsymmetrically substituted 2,2′-bipyridines have been developed. These bipyridines have found use in some novel homoleptic and heteroleptic ruthenium(II) complexes. Two methods for regiochemical control of nucleophilic addition to bpy have been explored: (i) mono N-oxidation followed by cyanation and subsequent hydrolysis gave 6-carboxy-2,2′-bipyridine (4); (ii) mono N-methylation followed by the conversion into 6-bromo-2,2′-bipyridine (12) and subsequent nucleophilic addition of lithioacetonitrile followed by hydrolysis of 6-cyanomethyl-2,2′-bipyridine (8) gave the homologous 2,2′-bipyridine-6-acetic acid (9). An established method of regioselective mono-ring alkylation of bpy using methyllithium yielded 6-methyl-2,2′-bipyridine (14), and the generation of the anion of 14 and subsequent addition to a chloromethyl oxazoline was applied to synthesize a second homologue, methyl 2,2′-bipyridine-6-propanoate (16). Structural determinations using 1H, 13C and 2D NMR spectroscopy permitted complete assignments of all signals in the 1H NMR spectra. Acta Chemica Scandinavica 1998.

Spectroelectrochemistry of Aromatic Ligands and Their Derivatives. 1. Reduction Products of 4,4'-Bipyridine, 2,2'-Bipyridine, 2,2'-Bipyrimidine, and Some Quaternized Derivatives

Cathodic reductions and reduction products of 4,4'-bipyridine (I), N-methyl-4,4'-bipyridinium+ (monoquat; II), N,N'-dimethyl-4,4'-bipyridinium2+ (paraquat; III), 2,2'-bipyridine (IV), 4,4'-dimethyl-2,2'-bipyridine (V), the ethylene-bridged diquaternized derivative 6,7-dihydrodipyridopyrazinedium2+ (diquat; VI), unbridged diquaternized N,N'-dimethyl-2,2'-bipyridinium2+ (VII), and 2,2'-bipyrimidine (VIII) have been investigated by cyclic voltammetry and spectroelectrochemistry.As expected, quaternization and the incorporation of added nitrogens in the ring both lead to easier reductions.The radicals formed by one-electron reduction of I-IV show very similar spectra, assignable in terms of a simple Hueckel molecular orbital scheme.Thus, N-methylation lowers the energy of the LUMO in I but does not alter its nature.The same scheme, after allowing for loss of symmetry, correlates with established treatments of the reduction products of IV, which we have extended to VI, VIII, and the related reduced species.In all cases studied, the reduction orbital is related to ?(7) of biphenyl, the transition ?(6) -> ?(7) moves, where the rings can rotate, to lower energy on reduction, and bands in the near IR-visible region are observed and assigned to transitions from ?(7) to higher orbitals.