10273-89-9

Basic information

• Product Name: 2-(o-tolyl)pyridine
• Synonyms: 2-(o-tolyl)pyridine;Einecs 233-618-6;Pyridine, 2-o-tolyl- (6CI,7CI,8CI);2-(2-Tolyl)pyridine
• CAS NO: 10273-89-9
• Molecular Formula: C₁₂H₁₁N
• Molecular Weight: 169.22244
• EINECS: 233-618-6
• Mol File: 10273-89-9.mol
• Article Data: 147

Chemical Properties

• Boiling Point: 150℃ (22 Torr)
• Flash Point: 109.2 °C
• Appearance: /
• Density: 1.03 g/cm³
• Vapor Pressure: 0.0131mmHg at 25°C
• Refractive Index: 1.5992 (589.3 nm 20℃)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 4.52±0.12(Predicted)
• CAS DataBase Reference: 2-(o-tolyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(o-tolyl)pyridine(10273-89-9)
• EPA Substance Registry System: 2-(o-tolyl)pyridine(10273-89-9)

Safety Data

• Hazardous Substances Data: 10273-89-9(Hazardous Substances Data)

Usage

General Description

2-(o-Tolyl)pyridine is a chemical compound with the molecular formula C14H12N. It belongs to the class of organic compounds known as tolylpyridines, which are aromatic compounds containing a pyridine ring substituted at the 2-position by a tolyl group. This chemical is commonly used in the synthesis of pharmaceuticals and agrochemicals due to its unique structure and reactivity. Its applications also extend to the field of materials science, where it is used as a building block for the synthesis of various organic materials and polymers. 2-(o-Tolyl)pyridine exhibits moderate toxicity and should be handled with caution in laboratory and industrial settings.

InChI:InChI=1/C12H11N/c1-10-6-2-3-7-11(10)12-8-4-5-9-13-12/h2-9H,1H3

Upstream product

• 110-86-1 pyridine 
• 105902-01-0 6-o-tolyl-2,3,4,5-tetrahydro-pyridine 
• 109-04-6 2-bromo-pyridine 
• 932-31-0 ortho-tolylmagnesium bromide 
• 16419-60-6 2-Methylphenylboronic acid 
• 5029-67-4 2-iodopyridine 
• 108-88-3 toluene 
• 33421-20-4 2-(2-methylphenyl)pyridine N-oxide 
• 98061-37-1 1-(2-(pyridin-2-yl)phenyl)methanol 
• 78715-82-9 1,2,3,5-thiatriazolo<5,4-a>pyridine 3-oxide 
• 529-19-1 2-Methylbenzonitrile 
• 74-86-2 acetylene 
• 109-09-1 2-chloropyridine 
• 95-46-5 2-methylphenyl bromide 

Downstream Products

• 110513-20-7 1-acetonyl-2-o-tolyl-pyridinium; iodide 
• 109102-05-8 1-methyl-2-o-tolyl-pyridinium; iodide 
• 244-99-5 4-azafluorene 
• 13764-20-0 2-(2-Pyridinyl)benzoic Acid 
• 98061-19-9 methyl 2-(2-pyridinyl)benzoate 

Relevant articles and documents

Manganese-catalyzed directed methylation of C(sp2)-H bonds at 25 °C with high catalytic turnover

We report here a manganese-catalyzed C-H methylation reaction of considerable substrate scope, using MeMgBr, a catalytic amount of MnCl2· 2LiCl, and an organic dihalide oxidant. The reaction features ambient temperature, low catalyst loading, typically 1%, high catalytic turnover reaching 5.9 × 103, and no need for an extraneous ligand and illustrates a unique catalytic use of simple manganese salts for C-H activation, which so far has relied on catalysis by manganese carbonyls.

Biphenylene-Substituted Ruthenocenylphosphine for Suzuki-Miyaura Coupling of Aryl Chlorides

High activity in the palladium-catalyzed Suzuki-Miyaura reactions of aryl chlorides with arylboronic acids was furnished using biphenylene-substituted di-tert-butylruthenocenylphosphine (R-Phos) as a supporting ligand. Substrate combinations even for the construction of highly hindered tetra-ortho- substituted biaryls can be achieved in good to excellent yields with low catalyst loadings in short reaction times.

Catalytic meta-selective C-H functionalization to construct quaternary carbon centres

A catalytic meta-selective C-H functionalization of 2-phenylpyridines using a range of tertiary halides is described. The protocol is simple to perform and uses commercially available reagents to construct challenging quaternary carbon centres in a regioselective manner. Preliminary studies suggest the C-H functionalization proceeds through a radical process directed via a remote σ-activation.

Cucurbit[8]uril recognition of rapidly interconverting diastereomers

The diastereoselectivity of Cucurbit[8]uril (CB[8]) binding was probed towards a series of rapidly interconverting diastereomers containing a Caryl-Caryl chiral axis and at least one other stereocenter. Relative binding affinities of up to 4.9 were determined when CB[8] interacted with ortho, meta, ortho′-substituted biphenyls bearing a chiral dialkylsulfonium substituent at their meta-position. Diastereoselectivities of up to 2.4-fold were obtained for ortho′-substituted 2-phenylpyridinium derivatives that bear a chiral myrtenyl N-substituent prone to CB[8] binding.

Palladium (II) Complexes Containing 2-Phenylpyridine Derivatives: Synthesis, Molecular Structures, and Catalytic Activity for Suzuki–Miyaura Cross-Coupling Reactions

The preparation and characterization of a series of new 2-phenylpyridine derivative ligands consisting of 2-(R) pyridine (R = mesityl (L1), 2,6-dimethylphenyl (L2), o-tolyl (L3), m-tolyl (L4), p-tolyl (L5), o-methoxyphenyl (L6), and p-methoxyphenyl (L7)) and their Pd complexes [PdCl2L2] (L1–L7) is investigated using a combination of X-ray diffraction spectroscopy, GC-MS, and NMR. The crystal structures show that the Pd complexes adopt a square planar geometry, and the monodentate ligand is coordinated through the N donor of the pyridine ring to the Pd atom. The catalytic activities of the synthesized complexes are investigated. The square planar Pd complex trans-[(2-mesitylpy)2PdCl2)] shows a high efficiency in promoting Suzuki-Miyaura cross coupling in an aqueous solvent under aerobic conditions.

Easily prepared air- and moisture-stable Pd-NHC (NHC = N-heterocyclic carbene) complexes: A reliable, user-friendly, highly active palladium precatalyst for the Suzuki-Miyaura reaction

The synthesis of NHC-PdCl2-3-chloropyridine (NHC = N-heterocyclic carbene) complexes from readily available starting materials in air is described. The 2,6-diisopropylphenyl derivative was found to be highly catalytically active in alkyl-alkyl Suzuki and Negishi cross-coupling reactions. The synthesis, ease-of-use, and activity of this complex are substantial improvements over in situ catalyst generation and all current Pd-NHC complexes. The utilization of complex 4 led to the development of a reliable, easily employed Suzuki-Miyama protocol. Employing various reaction conditions allowed a large array of hindered biaryl and drug-like heteroaromatic compounds to be synthesized without difficulty.

Does the 2-Pyridyl Cation Behave Like an Aryne ?

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α-Halo carbonyls enable: Meta selective primary, secondary and tertiary C-H alkylations by ruthenium catalysis

A catalytic meta selective C-H alkylation of arenes is described using a wide range of α-halo carbonyls as coupling partners. Previously unreported primary alkylations with high meta selectivity have been enabled by this methodology whereas using straight chain alkyl halides affords ortho substituted products. Mechanistic analysis reveals an activation pathway whereby cyclometalation with a ruthenium(ii) complex activates the substrate molecule and is responsible for the meta selectivity observed. A distinct second activation of the coupling partner allows site selective reaction between both components.

Palladium-catalyzed cross-coupling of aryl halides using organotitanium nucleophiles

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A unique six-membered chelated iridium complex

The reaction of 2-(3-methylbiphenyl-2-yl)pyridine with IrCl 3?nH2O in the presence of water incorporates a tightly bonded CO at the iridium center; in the subsequent reaction with picolinic acid a complex revealing an unusual CH activation of a methyl group is formed.

Rhoda-Electrocatalyzed C?H Methylation and Paired Electrocatalyzed C?H Ethylation and Propylation

The use of electricity over traditional stoichiometric oxidants is a promising strategy for sustainable molecular assembly. Herein, we describe the rhoda-electrocatalyzed C?H activation/alkylation of several N-heteroarenes. This catalytic approach has been successfully applied to several arenes, including biologically relevant purines, diazepam, and amino acids. The versatile C?H alkylation featured water as a co-solvent and user-friendly trifluoroborates as alkylating agents. Finally, the rhoda-electrocatalysis with unsaturated organotrifluoroborates proceeded by paired electrolysis.

A recyclable self-supported nanoporous PdCu heterogeneous catalyst for aqueous Suzuki-Miyaura cross-coupling

Nanoporous PdCu (NP-PdCu) was prepared by the dealloying strategy from a PdCuAl ternary alloy precursor and characterized systematically using SEM, TEM, XRD, and XPS. NP-PdCu was demonstrated to be a competent self-supported heterogenous catalyst for Suzuki-Miyaura cross-coupling, affording a series of synthetically valuable biaryl compounds in good to excellent yields. This catalyst could be easily separated from the productviacentrifugation and reused several times without obvious loss of catalytic performance.