933-69-7

Basic information

• Product Name: 5-METHYL-IMIDAZO[1,2-A]PYRIDINE
• Synonyms: 5-METHYL-IMIDAZO[1,2-A]PYRIDINE
• CAS NO: 933-69-7
• Molecular Formula: C₈H₈N₂
• Molecular Weight: 132.16
• Mol File: 933-69-7.mol

Chemical Properties

• Boiling Point: 96°C/0.7mm
• Flash Point: °C
• Appearance: /
• Density: 1.11g/cm³
• Refractive Index: 1.609
• PKA: 7.44±0.50(Predicted)
• CAS DataBase Reference: 5-METHYL-IMIDAZO[1,2-A]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYL-IMIDAZO[1,2-A]PYRIDINE(933-69-7)
• EPA Substance Registry System: 5-METHYL-IMIDAZO[1,2-A]PYRIDINE(933-69-7)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• HazardClass: IRRITANT
• Hazardous Substances Data: 933-69-7(Hazardous Substances Data)

Usage

Uses

Used in Research Studies:
5-Methyl-Imidazo[1,2-a]pyridine is used as a research compound for studying its chemical properties and potential applications in various fields. Its unique structure and characteristics make it a valuable subject for scientific investigation.
Used in Industrial Applications:
In the industrial sector, 5-Methyl-Imidazo[1,2-a]pyridine is employed as a chemical intermediate or building block for the synthesis of other organic compounds. Its specific use may vary depending on the requirements of the industry and the desired end products.
Used in Pharmaceutical Research:
Although its biological functions are not well defined, 5-Methyl-Imidazo[1,2-a]pyridine is used as a starting material in pharmaceutical research to explore its potential as a drug candidate or as a component in the development of new therapeutic agents.
Used in Chemical Synthesis:
5-Methyl-Imidazo[1,2-a]pyridine is utilized as a reactant in chemical synthesis processes, where it can be modified or combined with other compounds to create new molecules with specific properties and applications.

InChI:InChI=1/C8H8N2/c1-7-3-2-4-8-9-5-6-10(7)8/h2-6H,1H3

Upstream product

• 1824-81-3 2-Amino-6-methylpyridine 
• 107-20-0 2-chloroethanal 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 
• 17157-48-1 bromoacetaldehyde 

Downstream Products

• 178488-39-6 5-methylimidazo[1,2-a]pyridin-3-yl methanol 
• 1338248-81-9 5-methyl-3-phenylimidazo[1,2-a]pyridine 
• 1467064-03-4 3-(3-chlorophenyl)-5-methylimidazo[1,2-a]pyridine 
• 1414949-17-9 3-(4-Chlorophenyl)-2-phenylimidazo[1,2-a]pyridine 
• 1467064-05-6 3-(3-fluorophenyl)-5-methylimidazo[1,2-a]pyridine 
• 1467064-04-5 3-(2-chlorophenyl)-5-methylimidazo[1,2-a]pyridine 

Relevant articles and documents

Enantioselective Hydrogenation of Imidazo[1,2-a]pyridines

The enantioselective synthesis of tetrahydroimidazo[1,2-a]pyridines by direct hydrogenation was achieved using a ruthenium/N-heterocyclic carbene (NHC) catalyst. The reaction forgoes the need for protecting or activating groups, proceeds with complete regioselectivity, good to excellent yields, enantiomeric ratios of up to 98:2, and tolerates a broad range of functional groups. 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridines, which are found in numerous bioactive molecules, were directly obtained by this method, and its applicability was demonstrated by the (formal) synthesis of several functional molecules.

HETEROCYCLIC COMPOUND

Provided is a compound having an antagonistic action on an NMDA receptor containing the NR2B subunit, and is useful as a prophylactic or therapeutic agent for major depression, bipolar disorder, migraine, pain, peripheral symptoms of dementia and the like

Reactions with N-chlorosuccinimide of various 5-methylimidazo[1,2-a]pyridine derivatives with an electron-withdrawing group substituted at the 3-position

Chlorination reactions using N-chlorosuccinimide (NCS) was investigated for various 5-methylimidazo[1,2-a]pyridine derivatives with an electron-withdrawing group substituted at the 3-position. These reactions showed different results, and by examining these, we proposed a reaction mechanism via the appropriate 3-halogenoimidazo[1,2-a]pyridium compounds as the reaction intermediates.

Substituent effects on fluorescent properties of imidazo[1,2- α]pyridine-based compounds

In order to search for novel fluorescent organic compounds, 20 derivatives of imidazo[1,2-a]pyridine (1) were synthesized, and their fluorescent properties were studied. Though the parent compound I (λ(fl) = 370.5 nm, Φ = 0.57 in ethanol) was in the liquid state at ambient temperature, 2-phenylimidazo[1,2-a]pyridine (5), 2-(2-naphthyl)imidazo[1,2- a]pyridine (16), 7-methylimidazo[1,2-a]pyridine (3), 7-methyl-2- phenylimidazo[1,2-a]pyridine (12), and 7-methyl-2(2-naphthyl)imidazo[1,2- a]pyridine (17) were found to give thermally stable solid compounds (mp 55- 190 °C) without much affecting the fluorescent properties of the parent compound (λ(fl) = 374-381 nm, Φ = 0.50-0.78 in ethanol). Among the 4'- substituted 2-phenyl derivatives, it was found that the introduction of the strong electron-donating amino and dimethylamino groups (2-(4- aminophenyl)imidazo[1,2-a]pyridine (7) and 2-[4- (dimethylamino)phenyl]imidazo[1,2-a]pyridine (8), respectively) caused marked red shift of their fluorescence (λ(fl) = 445 and 446 nm, respectively, in ethanol), thus providing the way for tuning the fluorescence color of the IP derivatives. The observed red shift of the fluorescence of 7 and 8 was ascribed to the contribution of the excited intramolecular charge transfer state.

Synthesis of acyclo-C-nucleosides in the imidazo[1,2-a]pyridine and pyrimidine series as antiviral agents

The synthesis and the antiviral activities of C-3 acyclic nucleoside analogues of imidazo[1,2-a]pyridine and pyrimidine are reported. From these compounds, 20, 21, 22, 23, 28, and 34 showed a specific activity against cytomegalovirus and/or varicella-zoster virus.

Synthesis and antimuscarinic properties of some N-substituted 5- (aminomethyl)-3,3-diphenyl-2(3H)-furanones

In a study aimed toward developing new, selective antimuscarinic drugs with potential utility in the treatment of urinary incontinence associated with bladder muscle instability, a series of N-substituted 5-(aminomethyl)- 3,3-diphenyl-2(3H)-furanones, conformationally-constrained lactone relatives of benactyzine, was prepared. The compounds were examined in several paradigms that measure muscarinic (M1, M2, and M3) receptor antagonist activity. Selected members of the series that displayed potency and/or selectivity in these tests were studied for their effects on urinary bladder contraction, mydriasis, and salivation in guinea pigs. These studies revealed that incorporation of the amino functionality into an imidazole or pyrazole ring resulted in some novel, potent, and selective antimuscarinic agents. Appropriate alkyl substitution of position 2 of the imidazole strikingly affected muscarinic, particularly M3, receptor activity and may reflect a complementary site of interaction. Some of the compounds selectively reduced bladder pressure in a cystometrogram (CMG) model without producing concomitant mydriatic and salivary effects. The separate and distinct action of several compounds of this series in these in vivo protocols suggests the possibility of subtypes of muscarinic receptors that may correspond to previously characterized molecular cloned subpopulations. In this article, structure-activity relationships for the series of substituted lactones are discussed. These studies led to the identification of (R)-[(2-isopropyl-1H- imidazol-1-yl)methyl]-4,5-dihydro-3,3-diphenyl-2(3H)-furanone (23) as a clinical candidate for treating urinary bladder dysfunction.