37613-37-9

Basic information

• Product Name: 3-(4-fluorophenyl)-5-(4-methoxyphenyl)-1H-pyrazole
• Synonyms: 3-(4-fluorophenyl)-5-(4-methoxyphenyl)-1H-pyrazole
• CAS NO: 37613-37-9
• Molecular Weight: 268.29
• Mol File: 37613-37-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 3-(4-fluorophenyl)-5-(4-methoxyphenyl)-1H-pyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-fluorophenyl)-5-(4-methoxyphenyl)-1H-pyrazole(37613-37-9)
• EPA Substance Registry System: 3-(4-fluorophenyl)-5-(4-methoxyphenyl)-1H-pyrazole(37613-37-9)

Safety Data

• Hazardous Substances Data: 37613-37-9(Hazardous Substances Data)

Upstream product

• 7448-86-4 1-(4-methoxyphenyl)prop-2-en-1-one 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 2714-90-1 phenyl 4-fluorobenzoate 
• 123-11-5 4-methoxy-benzaldehyde 
• 5953-85-5 p-anisaldehyde hydrazone 
• 459-57-4 4-fluorobenzaldehyde 
• 401514-49-6 [(4-fluorophenyl)methylidene]hydrazine 
• 4181-97-9 phenyl 4-methoxybenzoate 
• 46318-58-5 4-methoxybenzoylnitromethane 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 102692-37-5 4-fluoro-4'-methoxy-trans-chalcone 
• 2965-64-2 1-(4-fluorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 

Relevant articles and documents

Heck Reactions of Acrolein or Enones and Aryl Bromides – Synthesis of 3-Aryl Propenals or Propenones and Consecutive Application in Multicomponent Pyrazole Syntheses

3-(Hetero)aryl propenals or propenones are efficiently prepared by a Heck reaction of (hetero)aryl bromides and acrolein or vinyl ketones using Beller's CataCXium Ptb ligand under Jeffery's and Fu's conditions. The formation of these three-carbon building blocks is embedded into consecutive three- and pseudo-four-component syntheses of 3-(hetero)aryl and 3,5-diarylpyrazoles with a broad substitution pattern in moderate to excellent yield.

Synthesis and theoretical study of a series of 3,5-disubstitutes pyrazoles

In this work, we proposed the synthesis of a series of pyrazoles derivatives with different substituents on the aromatic rings. We aim to evaluate their influence on the reactivity of the compounds in reactions of α,β-unsaturated chalcones and sulfonyl hydrazide catalyzed by iodine. In order to explain their high and low yields, or the impossibility of obtaining some compounds by applied synthetic methodology, Density Functional Theory (DFT) calculations were performed. The reaction Gibbs free energy (ΔG) as well as the energy gap of the HOMO-LUMO frontier orbitals (ΔE) of some selected reactants could explain qualitatively the experimental observations in terms of synthesis yield. In this way, we believe that the chemical nature of aromatic ring substituents is relevant for the reactivity of the starting materials as well as the formation of the desired products.

The diaza-Nazarov cyclization involving a 2,3-diaza-pentadienyl cation for the synthesis of polysubstituted pyrazoles

An unprecedented iodine-mediated diaza-Nazarov (DAN) type cyclization for the construction of substituted pyrazoles from easily available starting materials via an enamine-iminium ion intermediate is described. The oxidative cyclization worked under green conditions with remarkable regioselectivity. This one-pot, efficient and operationally simple three-component intramolecular regioselective DAN cyclization displayed a wide range of substrate scope. The dichotomy of reaction pathways has been explored with density functional theory in the gas phase and solution phase. Of the possible 1,5-, 1,6-, and 1,7-electrocyclizations, the DAN cyclization, i.e., the 1,5-pathway offers the lowest activation energy barrier supporting our experimental observations.