64091-87-8

Basic information

• Product Name: 3-(1-Methyl-1H-pyrazol-5-yl)pyridine
• Synonyms: 3-(1-Methyl-1H-pyrazol-5-yl)pyridine
• CAS NO: 64091-87-8
• Molecular Formula: C₉H₉N₃
• Molecular Weight: 159.18786
• Mol File: 64091-87-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 90-95 °C(Press: 0.01 Torr)
• Appearance: /
• Density: 1.13±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 4.74±0.12(Predicted)
• CAS DataBase Reference: 3-(1-Methyl-1H-pyrazol-5-yl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1-Methyl-1H-pyrazol-5-yl)pyridine(64091-87-8)
• EPA Substance Registry System: 3-(1-Methyl-1H-pyrazol-5-yl)pyridine(64091-87-8)

Safety Data

• Hazardous Substances Data: 64091-87-8(Hazardous Substances Data)

Upstream product

• 45887-08-9 3-(1H pyrazol-3-yl)-pyridine 
• 77-78-1 dimethyl sulfate 
• 55314-16-4 (E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one 
• 60-34-4 methylhydrazine 
• 74-88-4 methyl iodide 
• 1120-90-7 3-iodopyridine 
• 34091-51-5 5-iodo-1-methyl-1H-pyrazole 
• 350-03-8 methyl-3-pyridylketone 
• 930-36-9 1-methyl-1H-pyrazole 
• 626-55-1 3-Bromopyridine 
• 847818-74-0 1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole 

Relevant articles and documents

Selective Halogenation of Pyridines Using Designed Phosphine Reagents

Halopyridines are key building blocks for synthesizing pharmaceuticals, agrochemicals, and ligands for metal complexes, but strategies to selectively halogenate pyridine C-H precursors are lacking. We designed a set of heterocyclic phosphines that are installed at the 4-position of pyridines as phosphonium salts and then displaced with halide nucleophiles. A broad range of unactivated pyridines can be halogenated, and the method is viable for late-stage halogenation of complex pharmaceuticals. Computational studies indicate that C-halogen bond formation occurs via an SNAr pathway, and phosphine elimination is the rate-determining step. Steric interactions during C-P bond cleavage account for differences in reactivity between 2- and 3-substituted pyridines.

Selective palladium-catalyzed direct C-H arylation of unsubstituted N-protected pyrazoles

A highly selective C-5 arylation of N-dimethylaminosulfamoyl-protected pyrazole with aryl bromides is catalyzed by 2-5 mol% palladium in the presence of triphenylphosphine ligand and carboxylic acid additive. Selectivities up to 45:1 (C-5:C-4) can be achieved by running the reaction in non-polar solvents. A thorough study of scope and limitations shows good general tolerance of aryl bromide substitution. However, limitations on tolerance of ortho-subsitution and protic functional groups were established. Together with a telescoped deprotection step this method presents a viable alternative for the synthesis of C-3 arylated pyrazole building blocks.

Pd-catalysed direct 5-arylation of 1-methylpyrazole with aryl bromides

1-Methylpyrazole was found to be a suitable partner for palladium-catalysed direct arylation through C-H activation/functionalisation using aryl bromides. The reaction conditions and the nature of the catalyst were found to have a determining influence on