18441-60-6

Usage

Uses

Used in Organic Synthesis:
2,3,4,5-tetramethylpyridine is used as a strong, non-nucleophilic base for facilitating various organic synthesis reactions. Its ability to act as a base without participating in nucleophilic reactions makes it a valuable reagent in the formation of carbon-carbon and carbon-heteroatom bonds.
Used in Chemical Reactions as a Solvent:
2,3,4,5-tetramethylpyridine is employed as a solvent in chemical reactions, providing a suitable environment for the reactants to interact and form the desired products. Its solubility properties and stability contribute to the efficiency of the reactions.
Used in Pharmaceutical Production:
2,3,4,5-tetramethylpyridine is used as an intermediate in the production of pharmaceuticals. Its unique structure allows it to be a key component in the synthesis of various drug molecules, contributing to the development of new medications.
Used in Agrochemical Production:
2,3,4,5-tetramethylpyridine is utilized as an intermediate in the synthesis of agrochemicals, such as pesticides and herbicides. Its role in the production of these chemicals helps in the development of effective crop protection products.
Used in the Petroleum Industry as a Corrosion Inhibitor:
2,3,4,5-tetramethylpyridine is applied as a corrosion inhibitor in the petroleum industry. Its ability to prevent the corrosion of metal surfaces in pipelines and storage tanks is crucial for maintaining the integrity and safety of the petroleum infrastructure.

InChI:InChI=1/C9H13N/c1-6-5-10-9(4)8(3)7(6)2/h5H,1-4H3

Upstream product

• 857345-80-3 C-(4,5,6-trimethyl-[3]pyridyl)-methylamine 
• 91591-59-2 2-hydroxy-4,5,6-trimethyl-nicotinonitrile 
• 91591-64-9 2-chloro-4,5,6-trimethylpyridine-3-carbonitrile 
• 1016970-62-9 C₁₉H₂₉NSi 
• 1567-73-3 (E)-3-methylpent-3-en-2-one 
• 2450-71-7 Propargylamine 
• 857146-48-6 (4,5,6-Trimethyl-[3]pyridyl)-methanol 
• 874492-03-2 5-chloromethyl-2,3,4-trimethyl-pyridine 

Relevant academic research and scientific papers

NOVEL METHODS FOR PREPARATION OF SUBSTITUTED PYRIDINES AND RELATED NOVEL COMPOUNDS

The present invention relates to novel methods of preparation of substituted pyridines and the compounds produced therefrom. In particular, the present invention provides efficient methods for the construction of diversely substituted pyridines, with varying substitution patterns under simple and metal-free conditions with high atom- and pot-economy and excellent functional group tolerance, and which are useful for the synthesis of natural products.

A simple, tandem approach to the construction of pyridine derivatives under metal-free conditions: A one-step synthesis of the monoterpene natural product, (-)-actinidine

A simple and modular one-step synthesis of diversely substituted pyridines from readily available α,β-unsaturated carbonyl compounds and propargylic amines has been developed. The present protocol has a broad substrate scope and allows access to multi-substituted pyridines with select control of the substitution pattern under mild and metal-free conditions. The reaction involves imine formation followed by concomitant cyclization through an allenyl intermediate to afford pyridines in excellent yields, with water as the sole by-product. This mild strategy is also suitable for functionalization of natural products or other advanced intermediates having α,β-unsaturated carbonyl functionality. The utility of the present protocol was showcased with the synthesis of the monoterpene alkaloid, (-)-actinidine, an ant-associated iridoid.

Synthesis of dihydropyridines and pyridines from imines and alkynes via C-H activation

A convenient one-pot C-H alkenylation/electrocyclization/aromatization sequence has been developed for the synthesis of highly substituted pyridine derivatives from alkynes and α,β-unsaturated N-benzyl aldimines and ketimines that proceeds through dihydropyridine intermediates. A new class of ligands for C-H activation was developed, providing broader scope for the alkenylation step than could be achieved with previously reported ligands. Substantial information was obtained about the mechanism of the reaction. This included the isolation of a C-H activated complex and its structure determination by X-ray analysis; in addition, kinetic simulations using the Copasi software were employed to determine rate constants for this transformation, implicating facile C-H oxidative addition and slow reductive elimination steps.