116228-41-2

Basic information

• Product Name: 4-broMo-1-tosyl-1H-pyrazole
• Synonyms: 4-broMo-1-tosyl-1H-pyrazole;4-bromo-1H-pyrazol-1-yl(4-methylphenyl)sulfone;4-bromo-1-(4-methylphenyl)sulfonylpyrazole
• CAS NO: 116228-41-2
• Molecular Formula: C₁₀H₉BrN₂O₂S
• Molecular Weight: 301.15966
• EINECS: -0
• Mol File: 116228-41-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 102-103 °C
• Boiling Point: 440.7±47.0 °C(Predicted)
• Appearance: /
• Density: 1.63±0.1 g/cm3(Predicted)
• PKA: -6.11±0.19(Predicted)
• CAS DataBase Reference: 4-broMo-1-tosyl-1H-pyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-broMo-1-tosyl-1H-pyrazole(116228-41-2)
• EPA Substance Registry System: 4-broMo-1-tosyl-1H-pyrazole(116228-41-2)

Safety Data

• Hazardous Substances Data: 116228-41-2(Hazardous Substances Data)

Usage

General Description

4-bromo-1-tosyl-1H-pyrazole is a chemical compound with the molecular formula C11H9BrN2O2S. It is a pyrazole derivative with a bromine atom and a tosyl group attached to the 4-position of the pyrazole ring. 4-broMo-1-tosyl-1H-pyrazole is commonly used in organic synthesis as a versatile building block for the preparation of various pharmaceutical and agrochemical compounds. It is also known for its anti-inflammatory and analgesic properties, and has been studied for its potential therapeutic applications. Additionally, 4-bromo-1-tosyl-1H-pyrazole is used as a reagent in the synthesis of other heterocyclic compounds due to its reactivity and functional group tolerance. However, it is important to handle this compound with caution as it may pose health risks if not properly handled.

Upstream product

• 2075-45-8 4-bromo-1H-pyrazole 
• 98-59-9 p-toluenesulfonyl chloride 
• 1153-45-3 4-nitrophenyl 4-methylbenzenesulfonate 
• 288-13-1 NH-pyrazole 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 852471-30-8 1-[(4-methylphenyl)sulfonyl]-4-phenyl-1H-pyrazole 
• 6126-10-9 1-(4-toluenesulfonyl)-1H-pyrazole 

Relevant articles and documents

Synthesis of sulfonamides from azoles and sodium sulfinates at ambient temperature

NBS or NIS mediated direct S[sbnd]N bond formation between azoles and sodium sulfinates is described. The reaction shows good substrate scope and tolerates a wide range of functionalities in both azoles and sodium sulfinate substrates. Pyrazoles are also suitable for this method, various 4-halopyrazoles derivatives were obtained by using N-halosuccinimide (NXS) as the halogen source.

Direct synthesis of pyrazolo[5,1-a]isoindoles via intramolecular palladium-catalyzed C-H bond activation

An efficient, direct synthesis of pyrazolo-[5,1-a]isoindoles employing a palladium-catalyzed intramolecular C-H bond activation of 1-(2-halobenzyl) pyrazoles has been developed. The use of lithium chloride (LiCl) was found to be essential in these reactions, to suppress further C-H bond activation at the C-3 position of pyrazolo[5,1-a]isoindole, when C-3 is unsubstituted. This protocol can be applied to the synthesis of a pyrazolo[5,1-a]isoquinoline possessing a six-membered central ring system and a fully substituted pyrazolo[5,1-a]isoindole using sequential intra- and intermolecular C-H bond activation.

Radical cyclisation onto pyrazoles: Synthesis of withasomnine

A novel synthetic protocol for the synthesis of [1,2-b]-fused bicyclic pyrazoles has been developed using radical cyclisation. The protocol uses cyclisation of pyrazole-1-(ω-alkyl) radicals generated from 1-[ω-(phenylselenyl)alkyl]-pyrazole precursors. The pyrazole natural product, withasomnine (3-phenyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole), and larger ring analogues have been synthesised in good yield using the protocol. A Bu3SnH-mediated oxidative cyclisation mechanism is facilitated by azo or Et3B radical initiators acting as oxidants of the intermediate π-radicals.