33234-57-0

Basic information

• Product Name: 1H-Pyrrole, 3-(phenylmethyl)-
• CAS NO: 33234-57-0
• Molecular Formula: C11H11N
• Molecular Weight: 157.215
• Mol File: 33234-57-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1H-Pyrrole, 3-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole, 3-(phenylmethyl)-(33234-57-0)
• EPA Substance Registry System: 1H-Pyrrole, 3-(phenylmethyl)-(33234-57-0)

Safety Data

• Hazardous Substances Data: 33234-57-0(Hazardous Substances Data)

Upstream product

• 106369-30-6 N-tosyl-3-benzylpyrrolate 
• 109-97-7 pyrrole 
• 10575-94-7 N-benzyl-N-nitrosobenzamide 
• 63158-17-8 methyl 4-phenyl 2-butenoate 
• 100-52-7 benzaldehyde 
• 29897-82-3 N-benzylpyrrolidine 
• 100-51-6 benzyl alcohol 
• 81453-99-8 1-(phenylsulfonyl)-3-benzoylpyrrole 
• 34628-36-9 methyl 4-benzoyl-1H-pyrrole-2-carboxylate 
• 106369-21-5 N-[2-Benzyl-4,4-dimethoxy-2-(toluene-4-sulfonyl)-butyl]-4-methyl-benzenesulfonamide 
• 7126-41-2 3-benzoylpyrrole 

Downstream Products

• 1623751-85-8 (3-benzyl-1H-indo-7-yl)(p-tolyl)methanone 
• 1623752-06-6 C₂₃H₁₉NO₂ 

Relevant articles and documents

Metal-Free Directed C?H Borylation of Pyrroles

Robust strategies to enable the rapid construction of complex organoboronates in selective, practical, low-cost, and environmentally friendly modes remain conspicuously underdeveloped. Here, we develop a general strategy for the site-selective C?H borylation of pyrroles by using only BBr3 directed by pivaloyl groups, avoiding the use of any metal. The site-selectivity is generally dominated by chelation and electronic effects, thus forming diverse C2-borylated pyrroles against the steric effect. The formed products can readily engage in downstream transformations, enabling a step-economic process to access drugs such as Lipitor. DFT calculations (wB97X-D) demonstrate the preferred positional selectivity of this reaction.

Antimalarial activity of natural and synthetic prodiginines

Prodiginines are a family of linear and cyclic oligopyrrole red-pigmented compounds. Herein we describe the in vitro antimalarial activity of four natural (IC50 = 1.7-8.0 nM) and three sets of synthetic prodiginines against Plasmodium falciparum. Set 1 compounds replaced the terminal nonalkylated pyrrole ring of natural prodiginines and had diminished activity (IC 50 > 2920 nM). Set 2 and set 3 prodiginines were monosubstituted or disubstituted at either the 3 or 5 position of the right-hand terminal pyrrole, respectively. Potent in vitro activity (IC50 = 0.9-16.0 nM) was observed using alkyl or aryl substituents. Metacycloprodiginine and more potent synthetic analogues were evaluated in a P. yoelii murine patent infection using oral administration. Each analogue reduced parasitemia by more than 90% after 25 (mg/kg)/day dosing and in some cases provided a cure. The most favorable profile was 92% parasite reduction at 5 (mg/kg)/day, and 100% reduction at 25 (mg/kg)/day without any evident weight loses or clinical overt toxicity.

A NEW AND EFFECTIVE AMINOMETHYLATION BY THE USE OF N-(p-TOLUENESULFONYLMETHYL)-p-TOLUENESULFONAMIDE AS AN EQUIVALENT OF METHANIMINE. A CONVENIENT PREPARATION OF PYRROLE COMPOUNDS

Readily available N-(p-toluenesulfonylmethyl)-p-toluenesulfonamide was treated with base to generate N-methylene-p-toluenesulfonamide which reacted with a variety of nucleophiles forming the corresponding N-tosyl-aminomethylated compounds in good yields.Furthermore, the N-tosyl-aminomethylated acetals thus obtained were converted into the corresponding N-tosylpyrroles with the aid of acid catalyst in excellent yields.