1019-89-2

Basic information

• Product Name: 6-METHYL-2-PHENYL-IMIDAZO[1,2-A]PYRIDINE
• Synonyms: 6-METHYL-2-PHENYL-IMIDAZO[1,2-A]PYRIDINE
• CAS NO: 1019-89-2
• Molecular Formula: C₁₄H₁₂N₂
• Molecular Weight: 208.26
• Mol File: 1019-89-2.mol
• Article Data: 42

Chemical Properties

• Appearance: /
• Density: 1.11 g/cm³
• CAS DataBase Reference: 6-METHYL-2-PHENYL-IMIDAZO[1,2-A]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHYL-2-PHENYL-IMIDAZO[1,2-A]PYRIDINE(1019-89-2)
• EPA Substance Registry System: 6-METHYL-2-PHENYL-IMIDAZO[1,2-A]PYRIDINE(1019-89-2)

Safety Data

• Hazardous Substances Data: 1019-89-2(Hazardous Substances Data)

Usage

General Description

6-Methyl-2-phenyl-imidazo[1,2-a]pyridine, also known as MPIP, is a chemical compound with a fused imidazo[1,2-a]pyridine ring system. It is a heterocyclic aromatic compound with a molecular formula C13H11N3 and a molecular weight of 209.24 g/mol. MPIP is used in organic synthesis and pharmaceutical research as a building block for the synthesis of various other compounds and drugs. It is also studied for its potential pharmacological activities, including its role as an anti-cancer and anti-inflammatory agent. Additionally, MPIP may have applications in the field of materials science and as a fluorescent probe in biological imaging.

Upstream product

• 108-99-6 3-Methylpyridine 
• 35251-31-1 N-(1-phenylethylidene)-N-(4H-1,2,4-triazol-4-yl)amine 
• 19433-17-1 acetophenone O-acetyloxime 
• 1603-41-4 (5-methyl-pyridin-2-yl)amine 
• 100-41-4 ethylbenzene 
• 536-74-3 phenylacetylene 
• 4636-16-2 iodoacetophenone 
• 98-86-2 acetophenone 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 100-42-5 styrene 
• 1003-68-5 5-methyl-2-pyridone 
• 106-45-6 para-thiocresol 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 93745-54-1 6-methyl-3-nitroso-2-phenylimidazo[1,2-a]pyridine 
• 1622870-07-8 6-methyl-2,3-diphenylimidazo[1,2-a]pyridine 
• 1609583-46-1 6-methyl-2-phenyl-3-(phenylthio)imidazo[1,2-a]pyridine 

Relevant articles and documents

Iodine-catalyzed regioselective sulfenylation of imidazoheterocycles in PEG400

An iodine-catalyzed sulfenylation of imidazo[1,2-a]-pyridines, -pyrimidines, and [1,2-b]pyridazines is herein described with various thiophenols using hydrogen peroxide as an oxidizing agent in PEG400. The method enabled the formation of 3-arylthioimidazoheterocycles in moderate to excellent yields under metal-free conditions. Several functional groups were well tolerated under our optimized conditions. This journal is

One-pot synthesis of 2-phenylimidazo[1,2-α]pyridines from acetophenone, [Bmim]Br3 and 2-aminopyridine under solvent-free conditions

One-pot synthesis of 2-phenylimidazo[1,2-α]pyridines from acetophenone, [Bmim]Br3 and 2-aminopyridine under solvent-free conditions in the presence of Na2CO3, gave the corresponding 2-phenylimidazo[1,2-α]pyridines in excel

Solvent- and catalyst-free synthesis of imidazo[1,2-a]pyridines under microwave irradiation

A facile solvent- and catalyst-free method for the synthesis of a series of imidazo[1,2-a]pyridines in good to excellent yields by the condensation of 2-aminopyridines with α-bromoketones under microwave irradiation has been developed. The important featu

Copper-Catalyzed Aerobic Oxidative Cyclization of Ketoxime Acetates with Pyridines for the Synthesis of Imidazo[1,2-a]pyridines

A copper(I)-catalyzed aerobic oxidative coupling of ketoxime acetates with simple pyridines for the synthesis of imidazo[1,2-a]pyridines has been developed. This reaction tolerates a wide range of functional groups and it affords a series of valuable imidazo[1,2-a]pyridines in high yields under mild conditions.

Iron-Catalyzed Dehydrogenative sp3-sp2 Coupling via Direct Oxidative C-H Activation of Acetonitrile

An iron-catalyzed dehydrogenative sp3-sp2 coupling of acetonitrile and 2-arylimidazo[1,2-a]pyridine has been realized, which can serve as a novel approach toward heteroarylacetonitriles. The merit of this strategy is illustrated by the breadth of functional groups tolerated in the transformation and the fast access to pharmaceuticals (such as zolpidem) directly from the heteroarylacetonitriles.

Easy and efficient selenocyanation of imidazoheterocycles using triselenodicyanide

The regioselective selenocyanation of imidazoheterocycles using triselenodicyanide at room temperature is reported. The electrophilic aromatic substitution of a broad range of substrates is promoted by the triselenodicyanide obtained by oxidative coupling

Copper(I) iodide-catalysed aerobic oxidative synthesis of imidazo [1,2-α]pyridines from 2-aminopyridines and methyl ketones

We report here an operationally simple copper-catalysed synthesis of imidazo [1,2-α]pyridines through C-H activation with oxidative linkage of two C-N bonds under very mild conditions using molecular oxygen as a sole oxidant. The process allows the quick assembly of imidazo [1,2-α]pyridines including the antiulcer drug zolimidine from inexpensive and readily available 2-aminopyridines and methyl ketones with broad range of functional group tolerance.

Electrochemical oxidative selenylation of imidazo[1,2–a]pyridines with diselenides

Electrochemical oxidative selenylation of imidazo[1,2–a]pyridines has been developed. The reaction proceeds in an undivided electrochemical cell equipped with glassy carbon electrodes employing LiClO4 as a supporting electrolyte. This approach

Multicomponent Synthesis of Imidazo[1,2- a]pyridines: Aerobic Oxidative Formation of C-N and C-S Bonds by Flavin-Iodine-Coupled Organocatalysis

Herein, we report an aerobic oxidative C-N bond-forming process that enables the facile synthesis of imidazo[1,2-a]pyridines and takes advantage of a coupled organocatalytic system that uses flavin and iodine. Furthermore, the dual catalytic system can be applied to the one-pot, three-step synthesis of 3-thioimidazo[1,2-a]pyridines from aminopyridines, ketones, and thiols.

A simple and efficient route to 2-arylimidazo[1,2-a]pyridines and zolimidine using automated grindstone chemistry

A green and efficient mechanochemical method for the synthesis of a series of 2-arylimidazo[1,2-a]pyridines was developed using an electrical grinder. I2 catalyzed mechanochemical grinding facilitates the cyclocondensation reaction between various aryl methyl ketones and 2-aminopyridines to afford 2-arylimidazo[1,2-a]pyridines in good yields at ambient temperature. The method was successfully used for the gram-scale synthesis of a marketed drug, zolimidine. The noticeable advantages of this environmentally sustainable protocol include mild conditions, simple instrumentation, inexpensive catalyst, atom economy, short reaction time etc.

A multi pathway coupled domino strategy: I2/ TBHP-promoted synthesis of imidazopyridines and thiazoles via sp3, sp2 and sp C-H functionalization

I2/TBHP-promoted, one-pot, multi pathway synthesis of imidazopyridines and thiazoles has been achieved through readily available ethylarenes, ethylenearenes and ethynearenes. I2/TBHP as an initiator and oxidant is used to realize the C-H functionalization of this domino reaction. Simple and available starting materials, wide range of functional group tolerance, high potential for drug activity of the products and application in production are the advantageous features of this method.

Metal-free oxidative decarbonylative halogenation of fused imidazoles

An efficient strategy has been developed for the deformylative halogenation of carbaldehyde imidazo-fused heterocycles in the presence of TBHP controlled by temperature. A convenient and sequential functionalization (C8 to C3) portrays the synthetic utility of the current method.N-Heterocycle benzamide products were also observedviathe ring opening of imidazopyridines through the cleavage of C-C bond at high temperatures. Features of this method include temperature-controlled excellent regioselectivity, mild conditions and functional group tolerance.