1015-63-0

Usage

Class of compound

Aromatic heterocyclic (contains a five-membered ring with one nitrogen atom)

Structural characteristics

Pyrrole ring with four methyl groups and one phenyl group attached

Usage

Manufacturing of pharmaceuticals, dyes, and other organic compounds

Biological activity

Potential medicinal and pharmaceutical applications

Safety precautions

Proper handling and storage due to potential hazards

Upstream product

• 100710-49-4 2,4,5-trimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde 
• 38824-62-3 2,5-dimethyl-1-phenyl-pyrrole-3,4-dicarbaldehyde 
• 28895-02-5 3,4-dimethyl-2,5-hexanedione 
• 62-53-3 aniline 
• 122-66-7 diphenyl hydrazine 
• 503-17-3 dimethylacetylene 
• 1227476-15-4 Azobenzene 
• 7446-70-0 aluminium trichloride 
• 390407-18-8 (C₅H₅)2Zr(ONC₆H₅)C₄(CH₃)4 
• 70319-57-2 2,3,5-trimethyl-1-phenyl-1H-pyrrole 
• 83-24-9 2,5-dimethyl-1-phenyl-1H-pyrrole 
• 90085-77-1 1,4-Dibrom-1,2,3,4-tetramethyl-butadien-(1,3) 
• 586-96-9 Nitrosobenzene 
• 222851-56-1 N-phenylsulfinylamine 

Downstream Products

• 115695-77-7 C₃₆H₄₀N₂ 

Relevant academic research and scientific papers

Reactions of zirconacyclopentadienes with nitrosobenzene. Characterization of zirconacycle intermediates and formation of N-phenylpyrroles

Nitrosobenzene inserts into the Zr-C bond of zirconacyclopentadienes to give seven-membered zirconacyclic rings. The resulting insertion products are readily converted to N-phenylpyrroles and (in one case) a 3,3-spiroindole derivative.

Reactions of substituted (1,3 butadiene-1,4-diyl)magnesium, 1,4-bis(bromomagnesio)butadienes and 1,4-dilithiobutadienes with ketones, aldehydes and PhNO to yield cyclopentadiene derivatives and N-Ph pyrroles by cyclodialkenylation

1,4-Dilithiobutadiene derivatives 1, 1,4-bis(bromomagnesio)butadiene derivatives 2 and metallacyclic (1,3-butadiene-1,4-diyl)magnesium reagents 3 were prepared and their reactions with ketones, aldehydes, and PhNO were investigated. Multiply substituted c

Catalytic formal [2+2+1] synthesis of pyrroles from alkynes and diazenes via TiII/TiIV redox catalysis

Pyrroles are structurally important heterocycles. However, the synthesis of polysubstituted pyrroles is often challenging. Here, we report a multicomponent, Ti-catalysed formal [2+2+1] reaction of alkynes and diazenes for the oxidative synthesis of penta- and trisubstituted pyrroles: a nitrenoid analogue to classical Pauson-Khand-type syntheses of cyclopentenones. Given the scarcity of early transition-metal redox catalysis, preliminary mechanistic studies are presented. Initial stoichiometric and kinetic studies indicate that the mechanism of this reaction proceeds through a formally TiII/TiIV redox catalytic cycle, in which an azatitanacyclobutene intermediate, resulting from [2+2] alkyne + Ti imido coupling, undergoes a second alkyne insertion followed by reductive elimination to yield pyrrole and a TiII species. The key component for catalytic turnover is the reoxidation of the TiII species to a TiIV imido via the disproportionation of an η2-diazene-TiII complex.

TITANIUM (IV) COMPOUNDS AND METHODS OF FORMING HETEROCYCLIC COMPOUNDS USING SAME

The present disclosure provides Titanium (IV) compounds and methods of making heterocyclic compounds such as pyrroles using Titanium (IV) compounds. In certain embodiments, the Titanium (IV) compound is present in catalytic amounts.

Electrochemical oxidation and EPR spectroscopy of radical cations of N-substituted 2,3,4,5-Tetramethylpyrroles

Electrochemical oxidation of 19 N-substituted 2,3,4,5-tetramethylpyrroles has been studied in acetonitrile and dichloromethane by means of slow cyclic voltammetry and coulometry. The first oxidation consumes one electron and occurs within the potential range 0.60-0.94 V in acetonitrile and 0.78-1.17 V in dichloromethane (vs. SCE). Twelve in situ generated primary radical cations were sufficiently stable at lowered temperature in dichloromethane for EPR measurement and showed well resolved HFS. The g-values (≈2.0026) and the coupling constants of 2,5-methyls (aH≈1.5 mT), 3,4-methyls (aH≈0.35 mT), and of the pyrrole nitrogen (aN≈0.42 mT) are very proximate for all 12 radical cations. It can be concluded, with support from quantum chemical calculations, that the odd electron is localised entirely on the pyrrole ring in the a2 HOMO of the parent molecule. Despite the odd electron distribution, the stability of the radical cations depends on the particular substituent attached to the pyrrole nitrogen. Acta Chemica Scandinavica 1998.

Synthesis of Strained Heterobicycles from Alkynes and Heterocumulenes

A one-pot synthesis of strained heterobicycles such as 2-thia(or 2-aza)-3-iminobicyclohex-5-enes and 2-thia-3-azabicyclooct-7-ene 2-oxides from alkynes, aluminum halides, and heterocumulenes (isothiocyanates, carbodiimides, N-sulfinylaniline) is described.The thermal and acid-promoted reactions of the permethylated 2-thia-3-iminobicyclohex-5-ene 2 to monocyclic isomeres are reported.