33369-52-7

Basic information

• Product Name: methyl 1-methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate
• Synonyms: methyl 1-methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate;METHYL 1-METHYL-5-(P-TOLUOYL)-2-PYRROLYLACETAT;1-Methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetic acid methyl ester;TolMetin Methyl ester;SIXINSDWVSIFEY-UHFFFAOYSA-N
• CAS NO: 33369-52-7
• Molecular Formula: C₁₆H₁₇NO₃
• Molecular Weight: 271.31108
• EINECS: 251-480-5
• Mol File: 33369-52-7.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 427.6 °C at 760 mmHg
• Flash Point: 212.4 °C
• Appearance: /
• Density: 1.11
• Vapor Pressure: 1.62E-07mmHg at 25°C
• Refractive Index: 1.553
• PKA: -8.00±0.70(Predicted)
• CAS DataBase Reference: methyl 1-methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 1-methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate(33369-52-7)
• EPA Substance Registry System: methyl 1-methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate(33369-52-7)

Safety Data

• Hazardous Substances Data: 33369-52-7(Hazardous Substances Data)

Usage

General Description

Methyl 1-methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate is a chemical compound with the molecular formula C17H17NO3. It is a derivative of pyrrole and is commonly used in organic synthesis and pharmaceutical research. methyl 1-methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate is often used as a building block in the production of various pharmaceuticals and agrochemicals. Its unique structure and properties make it a valuable tool for researchers and industry professionals in the development of new drugs and agricultural products. Additionally, it has potential applications in the field of material science due to its interesting chemical properties. However, it is important to handle this compound with caution as it may have potential health and environmental hazards if not properly managed.

InChI:InChI=1/C16H17NO3/c1-11-4-6-12(7-5-11)16(19)14-9-8-13(17(14)2)10-15(18)20-3/h4-9H,10H2,1-3H3

Upstream product

• 14271-73-9 4-methylbenzoyl cyanide 
• 51856-79-2 N-methyl-2-(methoxycarbonylmethyl)pyrrole 
• 55174-52-2 4,N-dimethyl-benzimidoyl chloride 
• 144-55-8 sodium hydrogencarbonate 
• 874-60-2 4-methyl-benzoyl chloride 
• 107-06-2 1,2-dichloro-ethane 
• 83542-63-6 methyl 5-chlorocarbonyl-1-methylpyrrole-2-acetate 
• 563-43-9 ethylaluminum dichloride 
• 63833-44-3 morpholino(p-tolyl)methanone 
• 96-54-8 N-Methylpyrrole 
• 21898-59-9 1-methylpyrrole-2-acetic acid 
• 21898-43-1 2-(1-methyl-1H-pyrrol-2-yl)-2-oxoacetic acid 
• 201230-82-2 carbon monoxide 
• 624-31-7 4-tolyl iodide 

Downstream Products

• 62380-67-0 methyl 3-chloro-1-methyl-5-(p-toluoyl)pyrrole-2-acetate 
• 35711-34-3 tolmetin sodium 
• 26171-23-3 1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid 
• 1207070-75-4 (2-{2-[1-methyl-5-(4-methyl-benzoyl)-1H-pyrrol-2-yl]acetylamio}-acetylamino)acetic acid 2-methoxy-phenyl ester 
• 1207070-76-5 1-methyl-5-p-toluoylpyrrole-2-acetamidoacetic acid isopropyl alcohol ester 
• 93962-13-1 C₁₈H₂₀N₂O₄ 
• 104076-16-6 amtolmetin guacil 
• 87344-05-6 Tolmetin glycine amide 

Relevant articles and documents

Synthetic method of non-steroidal antiinflammatory drug pain killing

The invention discloses a synthesis method of non-steroidal anti-inflammatory drug tolmetin. The methodcomprises the following steps: sequentially preparing a sulfuric acid-containing acetonedicarboxylic acid crude product, 2-(2-acetoxy)-1-methyl-1H-pyrrole-3-formic acid and 2-(2-alkyl acetate)-1-methyl-1H-pyrrole-3-formic acid by taking citric acid or citric acid monohydrate as a raw material; and carrying out decarboxylation, acylation, hydrolysis and acidification to obtain tolmetin. The synthetic method provided by the invention overcomes the defect that the existing tolmetin preparation process depends on N-methylpyrrole, and is a low-cost, low-pollution and high-yield synthetic method of non-steroidal anti-inflammatory drug tolmetin.

Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations

Diazomethane is one of the most versatile reagents in organic synthesis, but its utility is limited by its hazardous nature. Although alternative methods exist to perform the unique chemistry of diazomethane, these suffer from diminished reactivity and/or correspondingly harsher conditions. Herein, we describe the repurposing of imidazotetrazines (such as temozolomide, TMZ, the standard of care for glioblastoma) for use as synthetic precursors of alkyl diazonium reagents. TMZ was employed to conduct esterifications and metal-catalyzed cyclopropanations, and results show that methyl ester formation from a wide variety of substrates is especially efficient and operationally simple. TMZ is a commercially available solid that is non-explosive and non-toxic, and should find broad utility as a replacement for diazomethane.

An Electrophilic Approach to the Palladium-Catalyzed Carbonylative C-H Functionalization of Heterocycles

A palladium-catalyzed approach to intermolecular carbonylative C-H functionalization is described. This transformation is mediated by PtBu3-coordinated palladium catalyst and allows the derivatization of a diverse range of heterocycles, including pyrroles, indoles, imidazoles, benzoxazoles, and furans. Preliminary studies suggest that this reaction may proceed via the catalytic formation of highly electrophilic intermediates. Overall, this provides with an atom-economical and general synthetic route to generate aryl-(hetero)aryl ketones using stable reagents (aryl iodides and CO) and without the typical need to exploit pre-metalated heterocycles in carbonylative coupling chemistry.