1132-37-2

Basic information

• Product Name: Pyridine, 2,2-methylenebis-
• Synonyms: Pyridine, 2,2-methylenebis-;2-(2-pyridylmethyl)pyridine;2-(pyridin-2-ylmethyl)pyridine;NSC 149982;Bis(pyridin-2-yl)methane;Bis(2-pyridyl)methane
• CAS NO: 1132-37-2
• Molecular Formula: C₁₁H₁₀N₂
• Molecular Weight: 170.2105
• Mol File: 1132-37-2.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 276.1°Cat760mmHg
• Flash Point: 103.9°C
• Appearance: /
• Density: 1.096g/cm³
• Vapor Pressure: 0.00826mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 4.95±0.12(Predicted)
• CAS DataBase Reference: Pyridine, 2,2-methylenebis-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine, 2,2-methylenebis-(1132-37-2)
• EPA Substance Registry System: Pyridine, 2,2-methylenebis-(1132-37-2)

Safety Data

• Hazardous Substances Data: 1132-37-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 3856, 1951 DOI: 10.1021/ja01152a088

InChI:InChI=1/C11H10N2/c1-3-7-12-10(5-1)9-11-6-2-4-8-13-11/h1-8H,9H2

Upstream product

• 110-86-1 pyridine 
• 1749-29-7 2-pyridylmethyllithium 
• 60-29-7 diethyl ether 
• 109-06-8 α-picoline 
• 109-04-6 2-bromo-pyridine 
• 75389-08-1 2,2-bis-(pyridin-2-yl)-acetonitrile 
• 931-19-1 2-methylpyridine N-oxide 
• 19437-26-4 2,2'-dipyridyl ketone 
• 2637-34-5 pyridine-2-thione 
• 6959-47-3 2-chloromethylpyridine hydrochloride 
• 4262-03-7 2-((pyridin-2-ylsulfide)methyl)pyridine 
• 55401-97-3 2-(Bromomethyl)pyridine 
• 947-88-6 3-pyridin-2-yl-[1,2,3]triazolo[1,5-a]pyridine 
• 372-48-5 2-fluoropyridine 

Downstream Products

• 25382-41-6 bis(2-piperidinyl)methane 
• 1432478-66-4 (2,2′-dipyridylmethane)Pt(Ph)₂ 
• 1355718-59-0 (dipyridin-2-ylmethyl)triphenylphosphonium bromide 
• 79057-57-1 α,α-bis(pyridin-2-yl)toluene 
• 19437-26-4 2,2'-dipyridyl ketone 

Relevant articles and documents

Role of the Bridging Group in Bis-Pyridyl Ligands: Enhancing Both the Photo- and Electroluminescent Features of Cationic (IPr)CuI Complexes

We report on the benefits of changing the bridging group X of bis-pyridyl ligands, that is, Py-X-Py where X is NH, CH2, C(CH3)2, or PPh, on the photo- and electroluminescent properties of a new family of luminescent cationic H-heterocyclic carbene (NHC) copper(I) complexes. A joint experimental and theoretical study demonstrates that the bridging group affects the molecular conformation from a planar-like structure (X is NH and CH2) to a boat-like structure (X is C(CH3)2 and PPh), leading to i) four-fold enhancement of the photoluminescence quantum yield (?em) without affecting the thermally activated delayed fluorescence mechanism, and ii) one order of magnitude reduction of the ionic conductivity (σ) of thin films. This leads to an overall enhancement of the device efficacy and luminance owing to the increased ?em and the use of low applied driving currents.

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Synthesis of methylene- and methine-bridged oligopyridines

A variety of methylene- and methine-bridged oligopyridines are conveniently accessible through stepwise nucleophilic aromatic substitution with fluoro-substituted pyridines. The yields achieved are regularly above 90%. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Synthesis and Isomeric Analysis of RuII Complexes Bearing Pentadentate Scaffolds

A RuII-pentadentate polypyridyl complex [RuII(κ-N5-bpy2PYMe)Cl]+ (1+, bpy2PYMe = 1-(2-pyridyl)-1,1-bis(6-2,2′-bipyridyl)ethane) and its aqua derivative [RuII(κ-N5-bpy2PYMe)(H2O)]2+ (22+) were synthesized and characterized by experimental and computational methods. In MeOH, 1+ exists as two isomers in different proportions, cis (70%) and trans (30%), which are interconverted under thermal and photochemical conditions by a sequence of processes: chlorido decoordination, decoordination/recoordination of a pyridyl group, and chlorido recoordination. Under oxidative conditions in dichloromethane, trans-12+ generates a [RuIII(κ-N4-bpy2PYMe)Cl2]+ intermediate after the exchange of a pyridyl ligand by a Cl- counterion, which explains the trans/cis isomerization observed when the system is taken back to Ru(II). On the contrary, cis-12+ is in direct equilibrium with trans-12+, with absence of the κ-N4-bis-chlorido RuIII-intermediate. All these equilibria were modeled by density functional theory calculations. Interestingly, the aqua derivative is obtained as a pure trans-[RuII(κ-N5-bpy2PYMe)(H2O)]2+ isomer (trans-22+), while the addition of a methyl substituent to a single bpy of the pentadentate ligand leads to the formation of a single cis isomer for both chlorido and aqua derivatives [RuII(κ-N5-bpy(bpyMe)PYMe)Cl]+ (3+) and [RuII(κ-N5-bpy(bpyMe)PYMe)(H2O)]2+ (42+) due to the steric constraints imposed by the modified ligand. This system was also structurally and electrochemically compared to the previously reported [RuII(PY5Me2)X]n+ system (X = Cl, n = 1 (5+); X = H2O, n = 2 (62+)), which also contains a κ-N5-RuII coordination environment, and to the newly synthesized [RuII(PY4Im)X]n+ complexes (X = Cl, n = 1 (7+); X = H2O, n = 2 (82+)), which possess an electron-rich Hκ-N4C-RuII site due to the replacement of a pyridyl group by an imidazolic carbene.

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C-Bridged Bispyrrolidines and Bispiperidines as New Ligands

The preparation of methylene-bridged C2-symmetric nitrogen-heterocycles as a new class of ligands is described, including methylene-bridged pyridines, quinolones, piperidines and pyrrolidines. These methylene-bridged aromatic systems are obtained via a microwave assisted Ziegler-type reaction. The separation of diastereomers and the application of the copper complexes of these ligands for cyclopropanation reactions proves the applicability of these new types of ligands.