37116-82-8

Basic information

• Product Name: 5,10,15,20-TETRA(2-NITROPHENYL)PORPHYRIN
• Synonyms: 5,10,15,20-TETRA(2-NITROPHENYL)PORPHYRIN
• CAS NO: 37116-82-8
• Molecular Formula: C₄₄H₂₆N₈O₈
• Molecular Weight: 794.73
• Mol File: 37116-82-8.mol
• Article Data: 21

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5,10,15,20-TETRA(2-NITROPHENYL)PORPHYRIN(CAS DataBase Reference)
• NIST Chemistry Reference: 5,10,15,20-TETRA(2-NITROPHENYL)PORPHYRIN(37116-82-8)
• EPA Substance Registry System: 5,10,15,20-TETRA(2-NITROPHENYL)PORPHYRIN(37116-82-8)

Safety Data

• Hazardous Substances Data: 37116-82-8(Hazardous Substances Data)

Upstream product

• 552-89-6 2-nitro-benzaldehyde 
• 109-97-7 pyrrole 

Downstream Products

• 123582-32-1 (meso-tetrakis(2-nitrophenyl)porphyrinato)cobalt(III) 
• 120120-01-6 nickel(II) meso-α,α,α,α-tetrakis(o-pivalamidophenyl)porphyrin 
• 122745-51-1 (meso-tetrakis(ortho-nitrophenyl)porphyrinato) chloromanganese(III) 
• 118115-08-5 5,10,15,20-tetra(2-nitrophenyl)porphyrin iron(III) chloride 
• 66887-83-0 meso-α,α,α,α-tetra-(o-nicotinamidophenyl)porphyrin 
• 74376-49-1 meso-tetra-α,α,α,α-(o-aminoacetamidophenyl)porphyrin 
• 85110-99-2 meso-α,α,α,α-tetra-(o-bromoacetamidophenyl)porphyrin 
• 68949-51-9 meso-β-(o-acetamidophenyl)-α,α,α-tris(o-acetamidophenyl)porphyrin 
• 55253-62-8 (α,α,α,α)-5,10,15,20-tetrakisphenyl>-21H,23H-porphine 

Relevant articles and documents

All Four Atropisomers of Iron Tetra(o- N, N, N-trimethylanilinium)porphyrin in Both the Ferric and Ferrous States

Electrostatic effects are key to many biological and (electro)chemical transformations, especially those that involve charged species. The position and orientation of the electric field with respect to the molecules undergoing charge rearrangement are often crucial to the progress of the reaction. Recently, several molecular (electro)catalysts have been designed to contain spatially positioned charged groups that can engage in specific intramolecular electrostatic interactions. For instance, iron complexes of the tetra(o-N,N,N-trimethylanilinium)porphyrin ligand, which has four cationic groups, have been used to great effect for both CO2 and O2 reduction. Because of the ortho-substitution pattern on the porphyrin ligand, there are four possible atropisomers - such as the αβαβ isomer with trimethylanilinium groups on alternating faces of the porphyrin - and thus four unique electrostatic environments. This study details the synthesis and characterization (1H NMR spectroscopy, single crystal X-ray diffraction, and cyclic voltammetry) of these four metalloporphyrin isomers in both the ferric (FeIII) and ferrous (FeII) forms by using a synthetic route that preserves atropisomeric purity. The atropisomers are different in some respects but show remarkable similarities in others, such as their reduction potentials. This study also shows that the widely-cited literature method used previously to prepare the molecular electrocatalyst for CO2 and O2 reduction yields a mixture of atropisomers rather than a single one, as was previously assumed. These results identify the ways in which intra- and intermolecular electrostatic effects affect both solution and solid-state properties as well underscoring the challenges associated with preparing metalloporphyrins with high atropisomeric purity.

Iron-Catalyzed Amination of Strong Aliphatic C(sp3)-H Bonds

A concept for intramolecular denitrogenative C(sp3)-H amination of 1,2,3,4-tetrazoles bearing unactivated primary, secondary, and tertiary C-H bonds is discovered. This catalytic amination follows an unprecedented metalloradical activation mechanism. The utility of the method is showcased with the short synthesis of a bioactive molecule. Moreover, an initial effort has been embarked on for the enantioselective C(sp3)-H amination through the catalyst design. Collectively, this study underlines the development of C(sp3)-H bond functionalization chemistry that should find wide application in the context of drug discovery and natural product synthesis.

Homolytic versus Heterolytic Hydrogen Evolution Reaction Steered by a Steric Effect

Several H?H bond forming pathways have been proposed for the hydrogen evolution reaction (HER). Revealing these HER mechanisms is of fundamental importance for the rational design of catalysts and is also extremely challenging. Now, an unparalleled example of switching between homolytic and heterolytic HER mechanisms is reported. Three nickel(II) porphyrins were designed and synthesized with distinct steric effects by introducing bulky amido moieties to ortho- or para-positions of the meso-phenyl groups. These porphyrins exhibited different catalytic HER behaviors. For these Ni porphyrins, although their 1e-reduced forms are active to reduce trifluoroacetic acid, the resulting Ni hydrides (depending on the steric effects of porphyrin rings) have different pathways to make H2. Understanding HER processes, especially controllable switching between homolytic and heterolytic H?H bond formation pathways through molecular engineering, is unprecedented in electrocatalysis.