7126-41-2

Basic information

• Product Name: 3-BENZOYLPYRROLE
• Synonyms: 3-BENZOYLPYRROLE;PHENYL-(1H-PYRROL-3-YL)-METHANONE;Ketorolac 3-Benzoylpyrrole IMpurity;3-Benzoyl-1H-pyrrole, [(1H-Pyrrol-3-yl)carbonyl]benzene;3-benzoyl-1H-pyrrole
• CAS NO: 7126-41-2
• Molecular Formula: C₁₁H₉NO
• Molecular Weight: 171.2
• Product Categories: Azoles;blocks
• Mol File: 7126-41-2.mol

Chemical Properties

• Melting Point: 88-90
• Boiling Point: 336.8°C at 760 mmHg
• Flash Point: 165.5°C
• Appearance: /
• Density: 1.173g/cm³
• Vapor Pressure: 0.00011mmHg at 25°C
• Refractive Index: 1.608
• Storage Temp.: 2-8°C
• PKA: 15.54±0.50(Predicted)
• CAS DataBase Reference: 3-BENZOYLPYRROLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BENZOYLPYRROLE(7126-41-2)
• EPA Substance Registry System: 3-BENZOYLPYRROLE(7126-41-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36
• Hazardous Substances Data: 7126-41-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Benzoylpyrrole is used as an intermediate in the synthesis of rac Ketorolac 6-Benzoyl Isomer (K235620), which is an isomeric impurity of Ketorolac (K235620). This application is significant because it contributes to the development of pharmaceutical compounds with potential therapeutic benefits.
In the pharmaceutical industry, 3-Benzoylpyrrole plays a vital role as a building block for the synthesis of various drugs. Its unique chemical properties allow it to be used in the creation of complex molecular structures that can target specific biological pathways, potentially leading to the development of new treatments for various diseases and conditions.
Furthermore, 3-Benzoylpyrrole's involvement in the synthesis of rac Ketorolac 6-Benzoyl Isomer highlights its importance in the production of impurity compounds. These impurities are essential for quality control and regulatory compliance in the pharmaceutical manufacturing process, ensuring the safety and efficacy of the final drug product.

InChI:InChI=1/C11H9NO/c13-11(10-6-7-12-8-10)9-4-2-1-3-5-9/h1-8,12H

Upstream product

• 109-97-7 pyrrole 
• 201230-82-2 carbon monoxide 
• 73728-29-7 para-ditritiumbenzene 
• 98-88-4 benzoyl chloride 
• 15373-02-1 4-benzoyl-1H-pyrrole-2-carboxaldehyde 
• 103872-47-5 [1-(tert-Butyl-dimethyl-silanyl)-1H-pyrrol-3-yl]-phenyl-methanone 
• 16851-82-4 N-phenylsulfonylpyrrole 
• 93-97-0 benzoic acid anhydride 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 768-03-6 Phenyl vinyl ketone 
• 2227-79-4 benzenecarbothioamide 
• 405219-07-0 1-(1-diethoxymethyl-1H-pyrrole-3-yl)phenylmethanone 
• 139261-90-8 3-benzoyl-N-p-toluenesulfonylpyrrole 
• 874-60-2 4-methyl-benzoyl chloride 

Downstream Products

• 499214-39-0 (2,4-dibenzoylpyrrol-1-yl)acetic acid ethyl ester 
• 153850-66-9 2,5-bis(1,3-benzodithiol-2-yl)-3-benzoylpyrrole 
• 1623751-87-0 (3-benzoyl-1H-indol-7-yl)(4-chlorophenyl)methanone 
• 1623751-86-9 (1H-indole-3,7-diyl)bis(phenylmethanone) 
• 1594782-17-8 5-(3-benzoyl-1H-pyrrol-1-yl)-2-nitrobenzaldehyde 
• 1594782-16-7 4-(3-benzoyl-1H-pyrrol-1-yl)-2-nitrobenzaldehyde 
• 1449787-47-6 (1-(1-hydroxy-1H-pyrazol-4-yl)-1H-pyrrol-3-yl)(phenyl)methanone 
• 1273148-19-8 [1-(2,4-difluoro-3-hydroxyphenyl)-1H-pyrrol-3-yl]phenylmethanone 
• 1273148-18-7 [1-(2,4-difluoro-3-methoxyphenyl)-1H-pyrrol-3-yl]phenylmethanone 
• 1225021-28-2 3-(3-benzoyl-1H-pyrrol-1-yl)propanenitrile 
• 1225021-27-1 C₁₇H₁₉NO₃ 
• 1225021-26-0 C₁₆H₁₇NO₃ 
• 158883-83-1 1-amino-3-benzoylpyrrole 
• 147088-89-9 2,4-dibenzoylpyrrole 

Relevant articles and documents

Ketorolac impurity C and preparation method and application thereof

The invention discloses a ketorolac impurity C and a preparation method and application thereof. According to the method, the ketorolac impurity C is prepared by taking pyrrole as an initial raw material through a series of reactions such as substitution,

Enhancing activity and selectivity in a series of pyrrol-1-yl-1-hydroxypyrazole-based aldose reductase inhibitors: The case of trifluoroacetylation

Aldose reductase (ALR2) has been the target of therapeutic intervention for over 40 years; first, for its role in long-term diabetic complications and more recently as a key mediator in inflammation and cancer. However, efforts to prepare small-molecule aldose reductase inhibitors (ARIs) have mostly yielded carboxylic acids with rather poor pharmacokinetics. To address this limitation, the 1-hydroxypyrazole moiety has been previously established as a bioisostere of acetic acid in a group of aroyl-substituted pyrrolyl derivatives. In the present work, optimization of this new class of ARIs was achieved by the addition of a trifluoroacetyl group on the pyrrole ring. Eight novel compounds were synthesized and tested for their inhibitory activity towards ALR2 and selectivity against aldehyde reductase (ALR1). All compounds proved potent and selective inhibitors of ALR2 (IC50/ALR2?=?0.043?0.242?μΜ, Selectivity index?=?190?858), whilst retaining a favorable physicochemical profile. The most active (4g) and selective (4d) compounds were further evaluated for their ability to inhibit sorbitol formation in rat lenses ex?vivo and to exhibit substrate-specific inhibition.

Hexafluoro-2-propanol-Promoted Intermolecular Friedel-Crafts Acylation Reaction

The intermolecular Friedel-Crafts acylation was carried out in hexafluoro-2-propanol to yield aryl and heteroaryl ketones at room temperature without any additional reagents.

An efficient and green method for regio- and chemo-selective Friedel-Crafts acylations using a deep eutectic solvent ([CholineCl][ZnCl2]3)

[CholineCl][ZnCl2]3, a deep eutectic solvent between choline chloride and ZnCl2, has been used as a dual function catalyst and green solvent for the Friedel-Crafts acylation of aromatic compounds instead of using the moisture-sensitive Lewis acids and volatile organic solvents. The reactions are performed with high yields under microwave irradiation with short reaction times for the synthesis of ketones. Interestingly, indole derivatives are regioselectively acylated in the 3-position under mild conditions with high yields without NH protection. Three new ketone products are synthesized. [CholineCl][ZnCl2]3 is easily synthesized from choline chloride and zinc chloride at a low cost, with easy purification and environmentally benign compounds. [CholineCl][ZnCl2]3 can be reused up to five times without loss of catalytic activity, making it ideal in industrial processes.

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 facile, highly efficient synthesis of fully N-confused calix[5]pyrrole

Fully N-confused calix[5]pyrroles 3 are prepared in high yield by the oligomerization of 3-hydroxyphenylmethylpyrrole 2 under acid-catalysed conditions at room temperature.

Diethoxymethyl protected pyrroles: Synthesis and regioselective transformations

Treatment of the acceptor-substituted pyrroles 1a-k with neat triethyl orthoformate gives access to the diethoxymethyl (DEM) protected derivatives 2a-k in high yield. Convenient and mild cleavage was achieved by subsequent treatment of the DEM-pyrroles 2a-k with trifluoroacetic acid in acetonitrile and aqueous NaOH at room temperature. DEM protection proved suitable for a variety of regioselective transformations involving directed orthometalation and iodine-magnesium exchange processes. Furthermore, electrophilic halogenations and Pd-catalyzed coupling reactions were also carried out.

The regioselective photoinduced aroylation at the 3-position of pyrrole derivatives

Irradiation of arenecarbothioamide with pyrrole or indole derivatives gave regioselectively 3-aroylpyrrole or -indole derivatives, respectively.

Antifungal agents. VIII. Synthesis and antifungal activities of bipyrryl analogues of bifonazole

Various bipyrryl analogues of bifonazole were synthesized starting from aryl-3-pyrryl-1-imidazolylmethanes. The introduction of a second pyrryl portion was performed by linking an acrylate moiety at 1-position of the pyrrole ring and then by treatment with TosMIC. The bipyrryl esters were hydrolyzed and decarboxylated to afford the required imidazoles. All new imidazole derivatives were tested against Candida albicans and Candida spp using as standard controls miconazole, bifonazole and ketoconazole.