4533-42-0

Basic information

• Product Name: 1-(4-NITROPHENYL)-1H-PYRROLE
• Synonyms: 1-(4-NITROPHENYL)-1H-PYRROLE;1-(4-NITROPHENYL)PYRROLE;Nitrophenyl-(1H)-pyrrole;1-(4-NITROPHENYL)-1H-PYRROLE 95%;1-(4-(Hydroxy(oxido)amino)phenyl)-1H-pyrrole;N-hydroxy-4-(1-pyrrolyl)benzeneamine oxide;N-hydroxy-4-pyrrol-1-ylbenzeneamine oxide;N-hydroxy-4-pyrrol-1-yl-benzeneamine oxide
• CAS NO: 4533-42-0
• Molecular Formula: C₁₀H₈N₂O₂
• Molecular Weight: 188.18
• Product Categories: Functional Materials;Pyrroles (for Conduting Polymer Research);Reagents for Conducting Polymer Research;pyrrole;Building Blocks;Heterocyclic Building Blocks;Pyrroles
• Mol File: 4533-42-0.mol

Chemical Properties

• Melting Point: 180-183 °C(lit.)
• Boiling Point: 327.7 °C at 760 mmHg
• Flash Point: 152 °C
• Appearance: /
• Density: 1.23 g/cm³
• Vapor Pressure: 0.00038mmHg at 25°C
• Refractive Index: 1.613
• CAS DataBase Reference: 1-(4-NITROPHENYL)-1H-PYRROLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-NITROPHENYL)-1H-PYRROLE(4533-42-0)
• EPA Substance Registry System: 1-(4-NITROPHENYL)-1H-PYRROLE(4533-42-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 4533-42-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-(4-NITROPHENYL)-1H-PYRROLE is used as a building block in organic synthesis for the creation of various pharmaceuticals and biologically active molecules. Its structural features facilitate the development of new compounds with potential therapeutic applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1-(4-NITROPHENYL)-1H-PYRROLE serves as a key intermediate, contributing to the synthesis of drugs with specific therapeutic targets and mechanisms of action.
Used in Materials Science:
1-(4-NITROPHENYL)-1H-PYRROLE is utilized in materials science for its potential to contribute to the development of new materials with unique properties, such as those with enhanced optical, electronic, or mechanical characteristics.
Used as a Fluorescent Probe in Biological Imaging:
1-(4-NITROPHENYL)-1H-PYRROLE is employed as a fluorescent probe in biological imaging, where its optical properties allow for the visualization and tracking of biological processes at the molecular level, aiding in research and diagnostics.

InChI:InChI=1/C10H8N2O2/c13-12(14)10-5-3-9(4-6-10)11-7-1-2-8-11/h1-8H

Upstream product

• 635-90-5 1-phenylpyrrole 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 100-01-6 4-nitro-aniline 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 636-98-6 p-nitrobenzene iodide 
• 109-97-7 pyrrole 
• 100-00-5 4-chlorobenzonitrile 
• 350-46-9 4-Fluoronitrobenzene 
• 586-78-7 para-nitrophenyl bromide 
• 113342-93-1 1-(4-Nitro-phenyl)-2,5-dihydro-1H-pyrrole 
• 51-35-4 4R-4-hydroxyproline 
• 5044-38-2 1-(4-chlorophenyl)-1H-pyrrole 
• 101130-93-2 N,N-diallyl-4-nitrobenzenamine 

Downstream Products

• 85754-51-4 4-hydroxy-6-(pyrrol-1-yl)quinoline-3-carboxylic acid 
• 1207680-81-6 4-chloro-N-{1-[2,2,2-trichloro-1-(4-nitrophenyl)-1H-pyrrol-2-yl]ethyl}benzenesulfonamide 
• 1207680-82-7 2,2,2-trichloro-1,1-bis[1-(4-nitrophenyl)-1H-pyrrol-2-yl]ethane 
• 1207680-74-7 N-{2,2,2-trichloro-1-[1-(4-nitrophenyl)-1H-pyrrol-2-yl]-ethyl}trifluoromethanesulfonamide 
• 1207680-75-8 N-{2,2,2-trichloro-1-[1-(4-nitrophenyl)-1H-pyrrol-3-yl]-ethyl}trifluoromethanesulfonamide 
• 1231714-70-7 2-(4,5-dimethylthiophen-2-yl)-1-(4-nitrophenyl)pyrrole 
• 1160861-82-4 N-(4-(1H-pyrrol-1-yl)phenyl)benzamide 

Relevant articles and documents

The third-order NLO properties of D-π-A molecules with changing a primary amino group into pyrrole

The nonlinear refractive index, as well as the two-photon absorption (TPA), has been investigated by the femto-second Z-scan method for push-pull molecules, in which a primary donor group is weakened by conversion into a pyrrole or related heterocycle. The results at the fast response time show that, contrary to what had been expected from a previous work, there is a little decrease in the nonlinear refractive index change by introduction of the weaker donor groups. Although the measured TPA spectra showed that the observed nonlinear refractive index change was regarded to be off-resonant; difference in the frequency dispersion among the molecules considerably contributes to the decrease, in addition to difference in the intrinsic static nonlinearity. This shows that there is some future in the development of these non-resonant materials.

A solvent-free manganese(II) -catalyzed Clauson-Kaas protocol for the synthesis of N-aryl pyrroles under microwave irradiation

The first manganese-catalyzed modified Clauson-Kaas reaction for N-substituted pyrrole synthesis using 2,5-dimethoxytetrahydrofuran with variously substituted aromatic amines has been developed (up to 89% yield). This interesting neat strategy is free from additives including co-catalysts, ligands, and acids. Relatively low cost, environmentally benign, and handy Mn(NO3)2·4H2O is employed as the catalyst under microwave conditions with a very short reaction time (20?min). The above qualities attest to the green nature of this reaction.

Sulphonic acid functionalized porphyrin anchored with a: Meso -substituted triazolium ionic liquid moiety: A heterogeneous photo-catalyst for metal/base free C-C cross-coupling and C-N/C-H activation using aryl chloride under visible light irradiation

We report an easy process to synthesize sulphonic acid functionalized porphyrin, anchored with a meso-substituted triazolium ionic liquid moiety (SAFPTILM) for metal/base free C-C cross-coupling and C-N/C-H activation using aryl chloride under visible light irradiation. The acid strength has been measured based on the Hammett indicator. The SAFPTILM photocatalyst comprising 18 π-conjugated electronic systems with the chromophore substituents in the meso-position can provide rapid electronic conducting channels during photocatalysis under the irradiation of visible light. It was found that SAFPTILM is an efficient photocatalyst for the Heck, Sonogashira, Buchwald, Ullmann/Fittig coupling and C-H activation of phenols with different aryl chlorides in the absence of a base/noble metal, using 5 W LED (yellow) light under ambient conditions. The photocatalyst with low band gap (1.55 eV) comprising conjugation, favors coupling reaction of unactivated aryl chlorides, by easy excitation of electrons and transfer to the conjugated benzimidazolium based phenylenediamine support delaying the recombination of photoinduced electron-hole pairs.

Novel substituted benzoyl compound and its pharmaceutically acceptable salt and preparation method and application (by machine translation)

The invention relates to the general formula I shown novel substituted benzoyl compound and its pharmaceutically acceptable salt and preparation method and application. The invention also provides pharmaceutical compositions containing them, in vitro and in vivo anti-tumor effect results and acute toxicity study, the obtained anti-tumor drug model substituted benzoyl compound, has more excellent anti-tumor activity and safety, can be in the treatment of leukemia, lung cancer, colon cancer, ovarian cancer and renal carcinoma tumor in the application, so that the therapeutic window, so in the medical field as antitumor agents in the very application value. (by machine translation)

A facile synthesis of 1-aryl pyrroles by clauson-Kaas reaction using oxone as a catalyst under microwave irradiation

A new and efficient methodology to synthesize N-substituted pyrrole derivatives by Clauson Kaas reaction employing Oxone as catalyst was developed. The transformation was performed in acetonitrile under microwave irradiation. This procedure has several advantages such as high yield, clean product formation, and short reaction time.

Solvent Free Synthesis of N-Substituted Pyrroles Catalyzed by Calcium Nitrate

Moderated and mild way for synthesizing N-substituted pyrrole has been demonstrated herein. No solvents need to be used for this reaction, and instead, reactants themselves acted as a reaction medium. In fact, the reaction is carried out using catalytic amount of Ca(NO3)2.4H2O. The reaction conditions are selective and mild that helped to tolerate a wide variety of functional groups to give the desired products in good chemical yields.

Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation

In the selective N-arylation of amines or azoles with aryl halidesa-, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and proceeds in moderate to high yield.

L -(-) -Quebrachitol as a Ligand for Selective Copper(0)-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles

l-(-)-Quebrachitol (QCT) has been found as a ligand of copper powder for selective N-arylation of nitrogen-containing heterocycles with aryl halides. Furthermore, another potential catalytic system (copper powder/QCT/t-BuOK) was successfully adapted to unactivated aryl chlorides.

Purpurine derivative electrochromic material and preparation method thereof

The invention discloses a purpurine derivative electrochromic material and a preparation method thereof. The preparation method comprises the steps that 4,4'-dipyridine is adopted as a raw material and undergoes a Menschutkin reaction with 1-chloro-2,4-di

Base-promoted nucleophilic fluoroarenes substitution of C–F bonds

With the use of KOH/DMSO as the superbase medium, the nucleophilic fluoroarene substitution for C–F bonds is presented. The transformation proceeds smoothly with the use of fluoroarenes bearing not only electron-withdrawing group, but also electron-donating group and a variety of nucleophiles such as alcohols, phenols, amines, amides and nitrogen-heterocyclic compounds. The double nucleophilic substitution using ortho-difluoroarenes and nucleophiles bearing ortho-dinucleophilic groups results in the formation of 2,3-dihydro-1,4-benzodioxins, dibenzo[b,e][1,4]dioxins and 10H-phenoxazines in moderate to good yields.