88328-13-6

Basic information

• Product Name: 1-phenyl-N-(2-(pyridin-2-yl)methyl)methanimine
• Synonyms: 1-phenyl-N-(2-(pyridin-2-yl)methyl)methanimine
• CAS NO: 88328-13-6
• Molecular Weight: 196.252
• Mol File: 88328-13-6.mol

Chemical Properties

• CAS DataBase Reference: 1-phenyl-N-(2-(pyridin-2-yl)methyl)methanimine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenyl-N-(2-(pyridin-2-yl)methyl)methanimine(88328-13-6)
• EPA Substance Registry System: 1-phenyl-N-(2-(pyridin-2-yl)methyl)methanimine(88328-13-6)

Safety Data

• Hazardous Substances Data: 88328-13-6(Hazardous Substances Data)

Upstream product

• 19198-87-9 N-[(1E)-pyridin-2-ylmethylidene]benzenemethanamine 
• 17881-80-0 (2-picolyl)trimethylsilane 
• 504-29-0 2-aminopyridine 
• 100-51-6 benzyl alcohol 
• 129760-63-0 C₉H₁₄NSi^(1-)*Li⁽¹⁺⁾ 
• 3731-51-9 2-(Aminomethyl)pyridine 
• 100-52-7 benzaldehyde 
• 10029-90-0 trans-2-phenyl-3-(2-pyridyl)aziridine 
• 622-79-7 benzyl azide 
• 100-46-9 benzylamine 

Downstream Products

• 1256973-99-5 (2S,3R,4S,5R)-4-benzoyl-2,3-diphenyl-5-(2-pyridyl)pyrrolidine 
• 1256973-97-3 (2S,3R,4S,5R)-4-nitro-2,3-diphenyl-5-(2-pyridyl)pyrrolidine 
• 1256974-04-5 4-nitro-2,3-diphenyl-5-(2-pyridyl)pyrrolidine 
• 1256973-93-9 (3aS,4S,6R,6aR)-4-(2-fluorophenyl)-2-methyl-6-(2-pyridyl)octahydropyrrolo[3,4-c]pyrrole-1,3-dione 
• 1256974-00-1 4-(2-fluorophenyl)-2-methyl-6-(2-pyridyl)octahydropyrrolo[3,4-c]pyrrole-1,3-dione 
• 1256973-70-2 (3aS,4S,6R,6aR)-2-methyl-4-phenyl-6-(2-pyridyl)-octahydropyrrolo[3,4-c]pyrrole-1,3-dione 
• 52095-67-7 bis(3-phenylimidazo[1,5-a]pyridine-1-yl)sulfide 
• 35854-46-7 3-phenylimidazo[1,5-a]pyridine 
• 916994-56-4 N-(2-pyridyl)methyl benzenecarbothioamide 
• 18081-89-5 2-(N-benzylaminomethyl)pyridine 
• 90-02-8 salicylaldehyde 
• 137129-33-0 2-((pyridin-2-ylmethylimino)methyl)phenol 
• 1408397-26-1 2,2,2-trifluoro-1-phenyl-N-(pyridin-2-ylmethyl)ethanamine 
• 1452864-12-8 N-benzyl-2,2,2-trifluoro-1-(pyridin-2-yl)ethanamine 

Relevant articles and documents

Rh(i)-catalysed imine-directed C-H functionalization: via the oxidative [3 + 2] cycloaddition of benzylamine derivatives with maleimides

The Rh(i)-catalysed imine-directed oxidative [3 + 2] cycloaddition of benzylamines with maleimides is reported. A wide range of both benzylamines and maleimides is applicable to the reaction. A one-pot three component strategy using benzylamines, 2-pyridi

Nickel Complexes Bearing N,N,O-Tridentate Salicylaldiminato Ligand: Efficient Catalysts for Imines Formation via Dehydrogenative Coupling of Primary Alcohols with Amines

Treatment of salicylaldiminato ligand L1H-L2H (L1H = 2,4-di-tert-butyl-6-((quinolin-8-ylimino)methyl)phenol; L2H = 2,4-di-tert-butyl-6-(((2-(diethylamino)ethyl)imino)methyl)phenol) with Ni(OAc)2·4H2O in refluxing ethanol afforded nickel complexes [(L1)Ni(OAc)] (1) and [(L2)Ni(OAc)] (2), respectively. Reaction of L3H (L3H = (2,4-di-tert-butyl-6-(((2-(pyridin-2-yl)ethyl)imino)methyl)phenol)) with Ni(OAc)2·4H2O in the presence of excess triethylanmine gave the dual ligands coordinated nickel complex [(L2)2Ni] (3). Complexes 1-3 were well characterized by high-resolution mass spectrometry, infrared spectroscopy, elemental analysis, and X-ray diffraction analysis. All the three Ni(II) complexes exhibited efficient activity and good selectivity in the acceptorless dehydrogenative coupling of alcohols and amines to produce imines and diimines. The present protocol provides an atom-economical and sustainable route for the synthesis of various imine derivatives by employing an earth-abundant nickel salt and easily prepared salicylaldiminato ligands.

Aerobic C?H Hydroxylation by Copper Imine Complexes: The Clip-and-Cleave Concept – Versatility and Limits

The intramolecular ligand hydroxylation of a series of copper(I) imine complexes during their reaction with dioxygen had been systematically studied. The so-called clip-and-cleave concept offers a facile way to oxygenate aldehydes or ketones. A copper(I)

Directed Hydroxylation of sp2 and sp3 C-H Bonds Using Stoichiometric Amounts of Cu and H2O2

The use of copper for C-H bond functionalization, compared to other metals, is relatively unexplored. Herein, we report a synthetic protocol for the regioselective hydroxylation of sp2 and sp3 C-H bonds using a directing group, stoichiometric amounts of Cu and H2O2. A wide array of aromatic ketones and aldehydes are oxidized in the carbonyl γ-position with remarkable yields. We also expanded this methodology to hydroxylate the β-position of alkylic ketones. Spectroscopic characterization, kinetics, and density functional theory calculations point toward the involvement of a mononuclear LCuII(OOH) species, which oxidizes the aromatic sp2 C-H bonds via a concerted heterolytic O-O bond cleavage with concomitant electrophilic attack on the arene system.

Direct and Stereospecific [3+2] Synthesis of Pyrrolidines from Simple Unactivated Alkenes

Pyrrolidines are important heterocyclic compounds with endless applications in organic synthesis, metal catalysis, and organocatalysis. Their potential as ligands for first-row transition-metal catalysts inspired a new method to access complex poly-heterocyclic pyrrolidines in one step from available materials. This fundamental step forward is based on the discovery of an essential organoaluminum promoter that engages unactivated and electron-rich olefins in intermolecular [3+2] cycloadditions.

Catalytic Manufacturing Method for Imine Having No Substituent Group on the Nitrogen, and Use for the Imine Produced

The present invention relates to a method for manufacturing an imine having no substituent group on the nitrogen by using, as a catalyst, a metal complex on an organic azide compound, and more specifically relates to a method in which a metal-complex catalyst is used to produce, from an organic azide having an alpha-hydrogen, an imine having no substituent group on the nitrogen via a continuous nitrogen removal and 1,2-hydrogen transfer reaction. The imine having no substituent group on the nitrogen manufactured by means of the method of the present invention can synthesise diverse coupling products comprising amine compounds by means of reactions with diverse nucleophiles.

Trans-Symmetric Dynamic Covalent Systems: Connected Transamination and Transimination Reactions

The development of chemical transaminations as a new type of dynamic covalent reaction is described. The key 1,3-proton shift is under complete catalytic control and can be conducted orthogonally to, or simultaneous with, transimination in the presence of an amine to rapidly yield two-dimensional dynamic systems with a high degree of complexity evolution. The transamination-transimination systems are proven to be fully reversible, stable over several days, compatible with a range of functional groups, and highly tunable. Kinetic studies show transamination to be the rate-limiting reaction in the network. Furthermore, it was discovered that readily available quinuclidine is a highly potent catalyst for aldimine transaminations. This study demonstrates how connected dynamic reactions give rise to significantly larger systems than the unconnected counterparts, and shows how reversible isomerizations can be utilized as an effective diversity-generating element. Constant exchange: The development of chemical transaminations as a new type of dynamic covalent reactions is described (see figure). This study demonstrates how connected dynamic reactions give rise to significantly larger systems than the unconnected counterparts, and shows how reversible isomerizations can be utilized as an effective diversity-generating element.

Copper(ii)-catalyzed trifluoromethylation of N-aryl imines

Methods for imine trifluoromethylation are of great importance because amines with trifluoromethylated stereogenic centers are useful building blocks for synthetic chemistry and drug discovery. Herein, we describe a new copper(ii)-catalyzed imine trifluoromethylation method without the use of Lewis base activators, presumably through cooperative activation.

N -(2-Pyridylmethyl)imines as azomethine precursors in catalytic asymmetric [3 + 2] cycloadditions

An efficient Cu(I)-catalyzed asymmetric [3 + 2] cycloaddition of N-(2-pyridylmethyl) imines has been developed. In the presence of a Cu(CH 3CN)4PF6/bisoxazoline catalyst system, high levels of enantioselectivity (up to 97% ee) and moderate to high exo selectivity were achieved with a wide variety of substituted dipolarophiles, including maleimides, fumarates, fumarodinitrile, enones, and nitroalkenes. The reaction with unsymmetrically substituted dipolarophiles is completely regioselective.

Pentacyclo-undecane derived cyclic tetra-amines: Synthesis and evaluation as potent anti-tuberculosis agents

As part of an ongoing effort to develop highly potent anti-tuberculosis agents, fourteen pentacyclo-undecane (PCU) tetra-amine compounds were synthesized and screened for their in vitro anti-mycobacterial activity against two TB strains, H37Rv and XDR 194 [an extensively drug-resistant strain of tuberculosis]. Using the broth macrodilution method, nitrofuranylamide based compounds (6a and 6b) showed almost similar activities against the H37Rv strain of Mycobacterium tuberculosis when compared with the control drug, ethambutol. N-Geranyl piperazine PCU (8a) and trans-trans farnesyl piperazine PCU (8b) were 3.2 and 3.7 times more potent than commercially available ethambutol. Both isoprenyl PCU tetra-amine derivatives and N-decyl piperazine PCU (9a) were highly active against the XDR 194 strain of tuberculosis with MICs in the range of 0.63-3.02 μM. Cytotoxicities (IC50) of isoprenyl based compounds (8a, 8b) and compound 9a were tested on a mammalian cell line [MDBK (Madin Darby bovine kidney epithelium)] with values of 30, 24 and 25 μM respectively.