6688-61-5

Basic information

• Product Name: 3-METHYL-3H-IMIDAZO[4,5-B]PYRIDINE
• Synonyms: 3-METHYL-3H-IMIDAZO[4,5-B]PYRIDINE
• CAS NO: 6688-61-5
• Molecular Formula: C₇H₇N₃
• Molecular Weight: 133.15058
• Mol File: 6688-61-5.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3-METHYL-3H-IMIDAZO[4,5-B]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYL-3H-IMIDAZO[4,5-B]PYRIDINE(6688-61-5)
• EPA Substance Registry System: 3-METHYL-3H-IMIDAZO[4,5-B]PYRIDINE(6688-61-5)

Safety Data

• Statements: 41
• Safety Statements: 26-39
• HazardClass: IRRITANT
• Hazardous Substances Data: 6688-61-5(Hazardous Substances Data)

Usage

General Description

3-Methyl-3H-imidazo[4,5-b]pyridine, also known as MIP, is a chemical compound with a molecular formula C9H7N3. It is a heterocyclic compound that contains both imidazole and pyridine rings. MIP is commonly used as a precursor in the synthesis of pharmaceutical compounds and in the development of organic electronic materials. It has also been studied for its potential biological activity, including its role as an agonist at the GABA receptor and as a modulator of neurotransmitter release. Additionally, MIP has been identified as a potential environmental contaminant and has been the subject of research into its fate and transport in the environment.

Upstream product

• 273-21-2 3H-imidazo[4,5-b]pyridine 
• 74-88-4 methyl iodide 
• 5028-20-6 3-amino-2-methylaminopyridine 
• 122-51-0 orthoformic acid triethyl ester 
• 4093-88-3 2-(methylamino)-3-nitropyridine 
• 1480-87-1 2-fluoro-3-nitropyridine 
• 5470-18-8 2-Chloro-3-nitropyridine 
• 452-58-4 2,3-Diaminopyridine 
• 68-12-2 N,N-dimethyl-formamide 
• 273-21-2 1H-Imidazo[4,5-b]pyridine 
• 64-18-6 formic acid 

Downstream Products

• 37805-78-0 6-bromo-3-methylimidazo<4,5-b>pyridine 
• 30458-68-5 2-chloro-3-methyl-3H-imidazo[4,5-b]pyridine 
• 1401817-89-7 2-(4-methoxyphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine 

Relevant articles and documents

Photoinduced Double Proton Tautomerism in 4-Azabenzimidazole

The proton-transfer tautomerism of 4-azabenzimidazole (4ABI) mediated by hydrogen bonding formation has been studied in the ground as well as in the excited state by means of absorption and emission spectroscopies. Thermodynamics of self-association and hydrogen-bonded complexes in nonpolar solvents were obtained. Proton-transfer isomers of 4ABI have been determined by syntheses and spectral characterization of various 4ABI methyl derivatives. The 4ABI dimer and 1:1 4ABI/acetic acid complex possessing cyclic dual hydrogen bonds undergoes a fast excited-state double proton-transfer reaction, resulting in a proton-transfer tautomer emission. Surprisingly, however, the ESDPT is prohibited in the 4ABI/2-azacyclohexanone cyclic hydrogen-bonded complex. The results render the conclusion that photoinduced double proton transfer in the 4ABI hydrogen-bonded complex can be fine-tuned by its associated guest molecule, as further supported by the molecular modeling as well as ab initio calculations.

Cu-Catalyzed C-H Allylation of Benzimidazoles with Allenes

CuH-catalyzed intramolecular cyclization and intermolecular allylation of benzimidazoles with allenes have been described. The reaction proceeded smoothly with the catalytic system of Cu(OAc)2/Xantphos and catalytic amount of (MeO)2MeSiH. This protocol features mild reaction conditions and a good tolerance of substrates bearing electron-withdrawing, electron-donating, or electron-neutral groups. A new catalytic mechanism was proposed for this copper hydride catalytic system.

C2-Selective Branched Alkylation of Benzimidazoles by Rhodium(I)-Catalyzed C-H Activation

Herein, we report a Rh(I)/bisphosphine/K3PO4 catalytic system allowing for the first time the selective branched C-H alkylation of benzimidazoles with Michael acceptors. Branched alkylation with N,N-dimethyl acrylamide was successfully applied to the alkylation of a broad range of benzimidazoles incorporating a variety of N-substituents and with both electron-rich and -poor functionality displayed at different sites of the arene. Moreover, the introduction of a quaternary carbon was achieved by alkylation with ethyl methacrylate. The method was also shown to be applicable to the C2-selective branched alkylation of azabenzimidazoles.

N-Substituted Formamides as C1-Sources for the Synthesis of Benzimidazole and Benzothiazole Derivatives by Using Zinc Catalysts

An efficient and convenient one-pot protocol has been developed for the synthesis of a variety of benzimidazole, benzoxazole, and benzothiazole derivatives. This novel approach uses various o-phenylenediamines and N-substituted formamides (C1 sources) in a zinc-catalyzed cyclization in the presence of poly(methylhydrosiloxane) to afford the corresponding derivatives as sole products in moderate to excellent yields.