583-58-4

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Lutidine is used as an intermediate in the preparation of active pharmaceutical ingredients (APIs) for the development of various medications. Its unique chemical structure allows it to be a key component in the synthesis of complex organic molecules, which can be further used to create therapeutic agents.
Used in Organic Synthesis:
3,4-Lutidine is used as a reagent and catalyst in various organic synthesis processes. Its ability to form stable complexes with metal ions makes it a valuable component in the synthesis of metal-organic frameworks (MOFs) and other coordination compounds.
Used in Chemical Research:
3,4-Lutidine is utilized in chemical research as a model compound to study the properties and reactions of heterocyclic aromatic amines. Its reactivity and stability make it an ideal candidate for investigating various chemical reactions and mechanisms.
Used in the Preparation of Tetrhydropyridine Derivatives:
3,4-Lutidine is used to prepare tetrhydropyridine derivatives by reduction. These derivatives are important in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds. The reduction of 3,4-Lutidine to tetrhydropyridine derivatives allows for the development of new compounds with potential applications in various industries.

Safety Profile

Poison by skin contact. Moderately toxic by ingestion and inhalation. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C7H9N/c1-6-3-4-8-5-7(6)2/h3-5H,1-2H3

Upstream product

• 118113-24-9 3,4-dimethyl-1,2-dihydro-pyridine 
• 72605-55-1 2,6-dichloro-3,4-dimethylpyridine 
• 462-95-3 formaldehyde diethyl acetal 
• 123-38-6 propionaldehyde 
• 110-86-1 pyridine 
• 779285-57-3 3,4-dimethyl-N-(methoxycarbonyl)pyridinium ion 
• 86260-31-3 3,4-lutidine-N-sulfonate 
• 108-89-4 picoline 
• 92670-28-5 (3,4-dimethylpyridinio)-N-phosphonate 
• 591-22-0 3,5-Lutidine 
• 119-65-3 isoquinoline 
• 108-99-6 3-Methylpyridine 
• 74-85-1 ethene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 6283-41-6 1,3,4-trimethylpyridinium iodide 
• 490-11-9 3,4-pyridinecarboxylic acid 
• 96938-75-9 2-(ethoxycarbonyl)-3-endo-4,8-trimethyl-2-azabicyclo<2.2.2>oct-7-ene-5,6-endo-dicarboxylic acid N-phenylimide 
• 96938-76-0 2-(ethoxycarbonyl)-3-endo-7,8-trimethyl-2-azabicyclo<2.2.2>oct-7-ene-5,6-endo-dicarboxylic acid N-phenylimide 
• 108-99-6 3-Methylpyridine 
• 86260-31-3 3,4-lutidine-N-sulfonate 
• 116037-23-1 3,4-Dimethyl-1-[2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-pyridinium; bromide 
• 55314-29-9 4-methylnicotinic acid ethyl ester 
• 94129-26-7 C₉H₁₃NO₃S 
• 36316-69-5 3,4-dimethylpyridinium chloride 
• 20350-26-9 2,4-dinitrophenolate 
• 779285-57-3 3,4-dimethyl-N-(methoxycarbonyl)pyridinium ion 
• 108-89-4 picoline 
• 92670-28-5 (3,4-dimethylpyridinio)-N-phosphonate 

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.

Mesoporous Aluminosilicates in the Synthesis of N-Heterocyclic Compounds

Abstract: The catalytic properties of samples of amorphous mesoporous aluminosilicate ASM with different Si/Al molar ratios (40, 80, 160) were studied in the synthesis of practically important pyridines (by the interaction of С2–С5 alcohols with formaldehyde and ammonia, cyclocondensation of acetaldehyde and propionic aldehyde with ammonia), dialkylquinolines and alkyltetrahydroquinolines (by reaction of aniline with C3, C4 aldehydes) and alkyldihydroquinolines (by interaction of aniline with ketones, acetone and acetophenone). It is found that mesoporous aluminosilicate ASM sample with a molar ratio of Si/Al = 40, which has the highest acidity among the studied samples, exhibits the highest activity and selectivity in these reactions.

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.

Template-free synthesis of high degree crystallinity zeolite y with micro-meso-macroporous structure

In this paper a new approach to the creation of a micro-meso-macroporous structure of Y zeolite was proposed. It was based on the selective crystallization into the integral cluster crystals of the preliminarily molded granules containing crystals of the zeolite in question and a porous binder matrix. The synthesized material was characterized by the high crystallinity degree of 95% and the volume of micro-, meso-, and macro-pores of 0.30, 0.15 and 0.15 cm3 g-1, respectively. It was shown that the Y zeolite with the hierarchical structure in H-form had the total acidity of about 830 μmol g-1 and revealed the high activity and selectivity in the synthesis of pyridines.

Synthesis of two potential heterocyclic amine food mutagens

(Chemical Equation Presented) The syntheses of two potential food mutagens formed during cooking, 2-amino-3,6,7-trimethyl-3H-imidazo[4,5-b]pyridine (1) and 2-amino-3,6,7-trimethyl-3H-imidazo[4,5-c]pyridine (2), are described.

DABCO and DMAP - Why are they different in organocatalysis?

(Chemical Equation Presented) What makes a good organocatalyst? DABCO (1,4-diazabicyclo[2.2.2]octane) is a thousandfold better nucleophile (k →) and at the same time a million times better leaving group (k←) than DMAP (4-(dimethylamino)pyridine). This apparent contradiction is resolved by consideration of the intrinsic reaction barriers.

Kinetics and mechanisms of the pyridinolysis of phenyl and 4-nitrophenyl chlorothionoformates formation and hydrolysis of 1-(aryloxythiocarbonyl) pyridinium cations

The title reactions are subjected to a kinetic study in water, at 25.0 °C, and an ionic strength of 0.2 M (KCl). By following the reactions spectrophotometrically two consecutive reactions are observed: the first is formation of the corresponding thionocarbamates (1-(aryloxythiocarbonyl)- pyridinium cations) and the second is their decomposition to the corresponding phenol and pyridine, and COS. Pseudo-first-order rate coefficients (k obsd1 and kobsd2, respectively) are found under excess amine. Plots of kobsd1 vs free pyridine concentration at constant pH are linear, with the slope (kN) independent of pH. The Bronsted-type plots (log kN vs pKa of the conjugate acids of the pyridines) are linear with slopes β = 0.07 and 0.11 for the reactions of phenyl and 4-nitrophenyl chlorothionoformates, respectively. These Bronsted slopes are in agreement with those found in other stepwise reactions of the same pyridines in water, where the formation of a tetrahedral intermediate is the rate-determining step. In contrast to the stepwise mechanism of the title reactions that for the reactions of the same substrates with phenols is concerted, which means that substitution of a pyridino moiety in a tetrahedral intermediate by a phenoxy group destabilizes the intermediate. The second reaction corresponds to the pyridine-catalyzed hydrolysis of the corresponding 1-(aryloxythiocarbonyl)pyridinium cation. Plots of k obsd2 VS free pyridine concentration at constant pH are linear, with the slope (kH) independent of pH. The Bronsted plots for kH are linear with slopes β = 0.19 and 0.26 for the reactions of the phenyl and 4-nitrophenyl derivatives, respectively. These low values are explained by the fact that as pKa increases the effect of a better pyridine catalyst is compensated by a worse leaving pyridine from the corresponding thionocarbamate.

Inhibitors of cell proliferation, angiogenesis, fertility, and muscle contraction

The invention concerns inhibitors of cell proliferation, angiogenesis, fertility, and muscle contraction, characterized by formula I wherein, X, Y and Z independently represent C or N; ------ is an optional double bond; n is 0 or 1; R1, R2, and R4 independently represent hydrogen, a chemical bond, C1-10 alkyl; C2-10 alkenyl; C2-10 alkinyl; aryl; aryl-C1-10 alkyl; C3-10 heterocyclyl; C5-10 heteroaryl; halo, CF3; NO2; NHC(O)R*, OR, said alkyl, alkenyl, alkinyl, aryl, arylalkyl, heterocyclyl, or heteroaryl being optionally substituted; R3, R5, and R6 independently represent hydrogen, C1-10alkyl; C2-10 alkenyl; C2-10 alkinyl; aryl; aryl-C1-10alkyl; C3-10 heterocyclyl; C5-10 heteroaryl; halo, CF3; NO2; NHC(O)R*, OR, said alkyl, alkenyl, alkinyl, aryl, heterocyclyl, or heteroaryl being optionally substituted; or R5 and R6 together form a 5- or 6-member aryl, heterocyclyl or heteroaryl group; R is hydrogen or C1-6 alkyl; R* is hydrogen, or C1-6 alkyl, or OH, wherein the optional substituents are preferably selected from the group of one to three OH, C1-6 alkyl, halo, NO2, C1-6 alkoxy, and CF3, or a pharmaceutically acceptable salt thereof.

A method for producing pyridine bases

A method for producing pyridine bases which comprises reacting in a gas-phase an aliphatic aldehyde, aliphatic ketone or mixture thereof with ammonia in the presence of a zeolite comprising titanium and/or cobalt and silicon as zeolite constituent elements in which the atomic ratio of silicon to titanium and/or cobalt is about 5 to 1000 gives improved yield.

AlCl3·6H2O/KI/CH3CN/ H2O system: An efficient general system for deoxygenation of organic N-oxides in hydrated media

An efficient general system for deoxygenation of organic N-oxides such as N-aryl nitrones, azoxy benzenes and N-heteroarene N-oxides uses AlCl3·6H2O/KI/CH3CN/H2O system at room temperature in hydrated media. The deoxygenated products were found in good yields.