3323-26-0

Basic information

• Product Name: 2-(4-Nitro-phenyl)-imidazo[1,2-a]pyridine
• Synonyms: Imidazo(1,2-a)pyridine, 2-(p-nitrophenyl)-;2-(p-Nitrophenyl)imidazo(1,2-a)pyridine
• CAS NO: 3323-26-0
• Molecular Formula: C₁₃H₉N₃O₂
• Molecular Weight: 239.24
• Product Categories: Fused Ring Systems
• Mol File: 3323-26-0.mol

Chemical Properties

• Appearance: /
• Density: 1.34 g/cm³
• Refractive Index: 1.686
• CAS DataBase Reference: 2-(4-Nitro-phenyl)-imidazo[1,2-a]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Nitro-phenyl)-imidazo[1,2-a]pyridine(3323-26-0)
• EPA Substance Registry System: 2-(4-Nitro-phenyl)-imidazo[1,2-a]pyridine(3323-26-0)

Safety Data

• Hazardous Substances Data: 3323-26-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-Nitro-phenyl)-imidazo[1,2-a]pyridine is used as a pharmaceutical candidate for its potential anti-cancer properties, targeting various types of cancer through its biological activities. It is also considered for its anti-inflammatory and antiviral properties, which can contribute to the development of new therapeutic agents.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-(4-Nitro-phenyl)-imidazo[1,2-a]pyridine serves as a key compound for the development of novel drugs, leveraging its biological activities and chemical structure to create new therapeutic agents with improved efficacy and safety profiles.
Used in Materials Science:
2-(4-Nitro-phenyl)-imidazo[1,2-a]pyridine is used in materials science for its fluorescence properties, which have potential applications in the development of organic light-emitting diodes and other optoelectronic devices. Its unique photophysical properties make it a promising candidate for advancing technologies in this field.

InChI:InChI=1/C13H9N3O2/c17-16(18)11-6-4-10(5-7-11)12-9-15-8-2-1-3-13(15)14-12/h1-9H

Upstream product

• 504-29-0 2-aminopyridine 
• 110944-98-4 2-iodo-1-(4-nitrophenyl)ethanone 
• 100-12-9 4-ethylnitrobenzene 
• 75-52-5 nitromethane 
• 555-16-8 4-nitrobenzaldehdye 
• 100-13-0 4-nitrostyrene 
• 14150-95-9 2-aminopyridine N-oxide 
• 937-31-5 (4-Nitrophenyl)acetylene 
• 110-86-1 pyridine 
• 90844-47-6 [1-(4-Nitro-phenyl)-eth-(E)-ylidene]-[1,2,4]triazol-4-yl-amine 
• 51738-10-4 2,2-dibromo-1-(4-nitrophenyl)ethene 
• 25407-30-1 4-nitrophenacylpyridinium bromide 
• 99-81-0 4-Nitrophenacyl bromide 
• 1021019-74-8 imidazo[1,2-a]pyridin-2-yl trifluoromethanesulfonate 

Downstream Products

• 1353511-86-0 2-(4-nitrophenyl)-3-phenylimidazo[1,2-a]pyridine 
• 118000-45-6 (4-Imidazo[1,2-a]pyridin-2-yl-phenyl)-carbamic acid ethyl ester 

Relevant articles and documents

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.

Solvent and catalyst-free synthesis of imidazo[1,2-a]pyridines by grindstone chemistry

The present work describes the solvent and catalyst-free synthesis of imidazo[1,2-a]pyridines in excellent to nearly quantitative yields from 2-aminopyridines and a wide variety of ω-bromomethylketones using a grindstone procedure at 25°C to 30°C for 3 to

Microwave-assisted synthesis and luminescent activity of imidazo[1,2-a]pyridine derivatives

In this work, a series of phenacyl bromide derivatives was synthesized and employed as key intermediate for the synthesis of substituted imidazo[1,2-a]pyridines. First, phenacyl bromide molecules were obtained from the bromination reaction of acetophenones assisted by microwave irradiation, obtaining the products 4a-v in a 15 minutes reaction with yields in the range of 50% to 99%. Subsequently, the conjugation of these molecules with 2-aminopyridine conduced to the production of imidazo[1,2-a]pyridine derivatives (7a-v) in a 60-second reaction with yields of 24% to 99%. Improved yields were determined with respect to those obtained with more tedious methodologies like thermally and mechanically assisted routes. Intense luminescence emissions in the purple and blue regions of the electromagnetic spectra were observed under UV excitation according to the nature of the substituents. This environmentally friendly methodology is expected to constitute an important class of organic compounds for the development of biomarkers, photochemical sensors, and medicinal applications.

SELECTIVE LIGANDS OF HUMAN CONSTITUTIVE ANDROSTANE RECEPTOR

The present invention provides a structurally novel class of heterocyclic compounds of general formula I wherein L1 is heteroaryl and L2 is heteroaryl or aryl. The novel compounds are useful in a method of prevention or treatment of a condition which is m

Imidazopyridine compound, pharmaceutical composition containing the same, and preparation method and application thereof (by machine translation)

Specifically discloses a pharmaceutical composition containing the compound and a pharmaceutically acceptable salt or a pharmaceutically acceptable solvate [1,2 - a] of the compound, and the preparation method, comprises the following steps of inhibiting, protein selectivity, drug effect strong STAT3 patent medicine, safety and the like, and the like . is particularly suitable for preventing and, or treating tumor growth and metastasis as well as pharmaceutical composition and pharmaceutical acceptable salt or pharmaceutically acceptable salt or pharmaceutically acceptable solvate of the compound in preparing STAT3 high-expression cell abnormal proliferation, form change and exercise function hyperthyroidism, and other related diseases / and are disclosed in the present invention. (by machine translation)

READ-THROUGH INDUCER AND PHARMACEUTICAL USE THEREOF

PROBLEM TO BE SOLVED: To provide a novel read-through inducer. SOLUTION: The present invention relates to a compound represented by the general formula (I) [each symbol in the formula is as described in the specification] or a pharmaceutically acceptable

PhI(OAc)2-mediated oxidative C[sbnd]H sulfoximination of imidazopyridines under mild conditions

A facile protocol for direct oxidative C[sbnd]N bond coupling of unactivated imidazo[1,2-a]pyridines with NH-sulfoximines was disclosed using sulfoximines as the nitrogen sources in the presence of (diacetoxy)iodobenzene (PhI(OAc)2). The reacti

Electrochemically initiated intermolecular C-N formation/cyclization of ketones with 2-aminopyridines: An efficient method for the synthesis of imidazo[1,2-: A] pyridines

Electrochemical intermolecular C-N formation/cyclization of ketones with 2-aminopyridines using catalytic hydriodic acid as the redox mediator was developed, providing imidazo[1,2-a]pyridines under more environmentally benign conditions. The reaction proceeds in a simple undivided cell, using low toxic ethanol as the solvent, without external oxidants, and exhibits high atom economy. A variety of ketones including acetophenones, unsatruated and alkyl ketones are amenable to this reaction, affording the corresponding products in moderate to excellent yields. A three-component tandem reaction realizing C-N, C-S/C-Se bond formation can also be achieved under standard conditions.

Ultrasound-assisted synthesis of imidazo[1,2-a]pyridines an d sequential one-pot preparation of 3-selanyl-imidazo[1,2-a]pyridine derivatives

A simple and rapid method to synthesize imidazo[1,2-a]pyridines starting from 2-aminopyridine and 2-bromoacetophenone derivatives under ultrasonic irradiation was developed. This protocol tolerates a wide range of 2-bromoacetophenone derivatives to produce a variety of imidazo[1,2-a]pyridines in good to excellent yields. Additionally, the one-pot preparation of 3-(organylselanyl)imidazo[1,2-a]pyridines via a sequential method is presented. In this case, different diorganyl diselenides were used as starting materials to afford the corresponding coupling products in excellent yields and short reaction times under sonication. The reactions were conducted in PEG-400, a cheap and nontoxic solvent, compatible with the ultrasound conditions in an environmentally benign process.

Eucalyptol: A new solvent for the synthesis of heterocycles containing oxygen, sulfur and nitrogen

We report here the first investigation of the use of eucalyptol as a new solvent for organic transformations. Heterocycles containing oxygen, sulfur and nitrogen were chosen as targets or as starting materials for widely used palladium-catalysed cross-cou