24423-89-0

Basic information

• Product Name: 2H-Pyrrole, 3,4-dihydro-5-phenyl-, 1-oxide
• Synonyms: 5-Phenyl-3,4-dihydro-2H-pyrrol-1-oxid;2H-Pyrrole,3,4-dihydro-5-phenyl-,1-oxide;5-phenyl-3,4-dihydro-2H-pyrrole-1-oxide;2-phenyl-1-pyrrolidine N-oxide
• CAS NO: 24423-89-0
• Molecular Formula: C10H11NO
• Molecular Weight: 161.203
• Mol File: 24423-89-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 101.5-102.5 °C
• Boiling Point: 302.9±25.0 °C(Predicted)
• Density: 1.10±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2H-Pyrrole, 3,4-dihydro-5-phenyl-, 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Pyrrole, 3,4-dihydro-5-phenyl-, 1-oxide(24423-89-0)
• EPA Substance Registry System: 2H-Pyrrole, 3,4-dihydro-5-phenyl-, 1-oxide(24423-89-0)

Safety Data

• Hazardous Substances Data: 24423-89-0(Hazardous Substances Data)

Upstream product

• 99075-08-8 1-Hydroxy-2-phenylpyrrolidine 
• 67-66-3 chloroform 
• 700-91-4 2-phenyl-1-pyrroline 
• 1006-64-0 2-(phenyl)pyrrolidine 
• 939-52-6 4-chloro-1-phenylbutan-1-one 
• 125363-43-1 4-Chloro-1-phenyl-butan-1-one oxime 
• 67-56-1 methanol 
• 58518-86-8 4-nitro-1-phenylbutan-1-one 

Downstream Products

• 1456784-36-3 2-allyl-2-phenyl-3,4-dihydro-2H-pyrrole 1-oxide 
• 1456784-40-9 2-allyl-5-phenyl-3,4-dihydro-2H-pyrrole 1-oxide 
• 1456784-38-5 2-allyl-2-phenylpyrrolidin-1-ol 
• 3042-21-5 2-methyl-5-phenyl-1H-pyrrole 

Relevant articles and documents

Metal-Free Solvent Promoted Oxidation of Benzylic Secondary Amines to Nitrones with H2O2

An environmentally benign protocol for the generation of nitrones from benzylic secondary amines via catalyst-free oxidation of secondary amines using H2O2 in MeOH or CH3CN is described. This methodology provides a selective access to a variety of C-aryl nitrones in yields of 60 to 93%. Several studies have been performed to shed light on the reaction mechanism and the role of the solvent.

Evasive neutral 2-aza-cope rearrangements. Kinetic and computational studies with cyclic nitrones

A full experimental study of the activation energy required for the hitherto unknown neutral 2-aza-Cope rearrangement is presented. A kinetic study of the process showed activation energies in the range of 22.91-24.06 kcal/mol, in agreement with a process operating at moderate temperature (70°C). Calculations at B3LYP/6-311+G(d,p) and M06-2X/6-311+G(d,p) levels of theory considering solvent (dimethyl sulfoxide (DMSO) and toluene) effects (PCM model) predict reaction energy barriers that are in agreement with the values obtained from 1H NMR-based kinetic experiments. Results obtained by using enantiomerically pure substrates demonstrate that the rearrangement takes place with complete transfer of chirality, in contrast to previously described cationic processes. The effects of solvent and acid catalysis, which converts the process into the more common cationic rearrangement, have also been studied. DFT calculations also predict correctly the acceleration of the process under acid catalysis, estimating energy barriers in the range of 16.80-18.57 kcal/mol. The hitherto unknown neutral 2-aza-Cope rearrangement of nitrones takes place under thermal conditions with complete transfer of chirality. The process can be catalyzed by acid through a classical cationic 2-aza-Cope rearrangement. Kinetic 1H NMR experiments and DFT theoretical studies have been used to estimate the activation parameters and determine the energy of activation of the process. Copyright

NOVEL PATHWAYS FOR THE FORMATION OF PHENYLPYRROLES

Treatment of 3-phenyl-5,6-dihydro-(4H)-1,2-oxazine (5) with KOH/DMSO at 100 grad C gave 2-phenylpyrrole (2a); similar treatment of the nitrone (6) gave 2-methyl-5-phenylpyrrole (12).