251-80-9

Basic information

• Product Name: 1H-Imidazo(1,2-b)pyrazole
• Synonyms: 1H-Imidazo(1,2-b)pyrazole;imidazopyrazole
• CAS NO: 251-80-9
• Molecular Formula: C₅H₅N₃
• Molecular Weight: 107.1133
• Mol File: 251-80-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.41g/cm³
• Refractive Index: 1.739
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1H-Imidazo(1,2-b)pyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazo(1,2-b)pyrazole(251-80-9)
• EPA Substance Registry System: 1H-Imidazo(1,2-b)pyrazole(251-80-9)

Safety Data

• Hazardous Substances Data: 251-80-9(Hazardous Substances Data)

Usage

General Description

1H-Imidazo(1,2-b)pyrazole is a chemical compound that belongs to the class of imidazo[1,2-b]pyrazole derivatives. It has a fused imidazo[1,2-b]pyrazole ring system, which is composed of an imidazole and a pyrazole ring. 1H-Imidazo(1,2-b)pyrazole has potential applications in pharmaceutical and agrochemical industries due to its diverse biological activities, such as anti-inflammatory, antiviral, and anticancer properties. Additionally, it is a key intermediate in the synthesis of various biologically active compounds and ligands for metal-catalyzed reactions. The development and utilization of 1H-Imidazo(1,2-b)pyrazole derivatives contribute to the advancement of medicinal chemistry and drug discovery research.

InChI:InChI=1/C5H5N3/c1-2-7-8-4-3-6-5(1)8/h1-4,6H

Upstream product

• 135829-81-1 5-amino-1-(2,2-diethoxyethyl)-pyrazole-4-carboxylic acid 
• 135829-73-1 1-(2,2-diethoxyethyl)-5-aminopyrazole 
• 222055-80-3 5-amino-1-(2,2-diethoxy-ethyl)-1H-pyrazole-4-carboxylic acid ethyl ester 

Downstream Products

• 135830-23-8 1-acetyl-1H-imidazo[1,2-b]-pyrazole 
• 188998-04-1 1-formyl-1H-imidazo[1,2-b]pyrazole 

Relevant articles and documents

Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof

Compositions for the oxidative dyeing of keratin fibers, comprising a medium suitable for dyeing and at least one bicyclic fused 5-5-membered aza heteroaromatic keratin dyeing compounds having a ring junction nitrogen and an N-hydroxy or N-amino group and derivatives thereof. A method for oxidative dyeing of keratin fibers, comprising applying such compositions in the presence of an oxidizing agent, for a period sufficient to develop the desired coloration.

Synthesis of mono- and disubstituted 1H-imidazo[1,2-b]pyrazoles

The improved synthesis of 1H-imidazo[1,2-b]pyrazole 1 and of mono- and disubstituted derivatives is described and representative experimental procedures are given. Namely, 2-, 3-, 7- and 6-monosubstituted (2-15k), 2,3- and 6,7-disubstituted (16,17) compounds are prepared and characterized.

Synthesis of novel derivatives of 1H-imidazo[1,2-b]pyrazole as potential CNS-agents

As part of a preliminary study on novel 5-HT3 ligands, the synthesis of a series of 1H-imidazo[1,2-b]-pyrazole derivatives is described. The bicyclic heteroaromatic nucleus was functionalized as positions 1, 6 and 7 to give the series of tropanyl derivatives 4a-g, 12a, 12d. Different synthetic approaches were utilized to obtain the desired molecules: endo and exo 6-amides 4a, 12a and 6-ester 4b required two independent schemes due to the opposite behavior of the intermediate imidazolide 3 towards tropine and tropanamine. The 7-congeners, ester 4c, its tropinium salt 4e, the endo and exo amides 4d and 12d were prepared from the known common precursor 8, while derivatives 4f-g, originated by functionalizing position 1, were obtained from 1H-imidazo[1,2-b]pyrazole by direct N-acylation. Since the structural features of these molecules seemed to meet the main rules of the S.A.R. studies published so far, they were evaluated 'in vitro' for 5-HT3 receptor affinity. The biochemical data show significant activity for derivatives 4a-e, 4g. These results are encouraging and justify further investigational work on this class of molecules.