52459-90-2

Basic information

• Product Name: 1H-Pyrrole-3-carboxylicacid,2,4-dimethyl-,methylester(9CI)
• Synonyms: 1H-Pyrrole-3-carboxylicacid,2,4-dimethyl-,methylester(9CI);2,4-Dimethyl-1H-pyrrole-3-carboxylic acid methyl ester;1H-pyrrole-3-carboxylic acid, 2,4-dimethyl-, methyl ester;methyl 2,4-dimethyl-1H-pyrrole-3-carboxylate;methyl 2,4-dimethyl-1H-pyrrole-3-carboxylate(SALTDATA: FREE)
• CAS NO: 52459-90-2
• Molecular Formula: C₈H₁₁NO₂
• Molecular Weight: 153.18
• Product Categories: CARBOXYLICESTER
• Mol File: 52459-90-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 276.7°Cat760mmHg
• Flash Point: 121.2°C
• Appearance: /
• Density: 1.108g/cm³
• Vapor Pressure: 0.00471mmHg at 25°C
• Refractive Index: 1.521
• CAS DataBase Reference: 1H-Pyrrole-3-carboxylicacid,2,4-dimethyl-,methylester(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole-3-carboxylicacid,2,4-dimethyl-,methylester(9CI)(52459-90-2)
• EPA Substance Registry System: 1H-Pyrrole-3-carboxylicacid,2,4-dimethyl-,methylester(9CI)(52459-90-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 52459-90-2(Hazardous Substances Data)

Usage

Description

1H-Pyrrole-3-carboxylic acid, 2,4-dimethyl-, methyl ester (9CI) is a heterocyclic aromatic organic compound with the molecular formula C9H11NO2. It is a methyl ester derivative of 1H-pyrrole-3-carboxylic acid, known for its potential pharmacological properties and is being studied for its potential use in the treatment of various medical conditions. This chemical is commonly used in the pharmaceutical industry for the synthesis of various drugs and pharmaceutical compounds, and also utilized in organic synthesis as a building block for the creation of complex molecules. However, it is important to handle this chemical with care due to its potential hazards and toxic effects.

Uses

Used in Pharmaceutical Industry:
1H-Pyrrole-3-carboxylic acid, 2,4-dimethyl-, methyl ester (9CI) is used as a key intermediate in the synthesis of various drugs and pharmaceutical compounds for its versatile chemical properties and potential pharmacological activities.
Used in Organic Synthesis:
1H-Pyrrole-3-carboxylic acid, 2,4-dimethyl-, methyl ester (9CI) is used as a building block in the creation of complex molecules, contributing to the development of new chemical entities with potential applications in various fields.

InChI:InChI=1/C8H11NO2/c1-5-4-9-6(2)7(5)8(10)11-3/h4,9H,1-3H3

Upstream product

• 107-41-5 2-methyl-2,4-pentanediol 
• 62264-99-7 methyl 5-acetyl-2,4-dimethyl-1H-pyrrole-3-carboxylate 
• 107-21-1 ethylene glycol 
• 540-63-6 ethane-1,2-dithiol 
• 112561-10-1 methyl-bis(trimethylsilyl)aminomethylpropiolate 
• 75-36-5 acetyl chloride 
• 1286715-92-1 C₈H₁₃NO₃ 
• 90433-94-6 methyl 2,4-dimethyl-5-(2-methyl-1,3-dithiolan-2-yl)-1H-pyrrole-3-carboxylate 
• 18913-35-4 methyl buta-2,3-dienoate 
• 73857-68-8 2-methyl-1,3-dithiolan-2-yl perchlorate 
• 90433-95-7 methyl 5-(2-methyl-1,3-dithiolan-2-yl)-1,2,4-trimethyl-1H-pyrrole-3-carboxylate 

Downstream Products

• 154700-02-4 benzyl 3-ethyl-4'-methoxycarbonyl-4,3',5'-trimethyl-2,2'-dipyrrylmethane-5-carboxylate 
• 138648-25-6 benzyl 3-ethyl-4'-methoxycarbonyl-3',5'-dimethyl-2,2'-dipyrrylmethane-5-carboxylate 
• 138648-41-6 benzyl 3,8,17-triethyl-2,12,18-trimethyl-13,15-(13'-oxo)ethanoporphyrin-15'-carboxylate 
• 138648-40-5 3-Oxo-3-((1Z,4Z,9Z,15Z)-7,12,18-triethyl-3,13,17-trimethyl-porphyrin-2-yl)-propionic acid benzyl ester 

Relevant articles and documents

Regioselective synthesis of 2,3,4- or 2,3,5-trisubstituted pyrroles via [3,3] or [1,3] rearrangements of O-vinyl oximes

The regioselective synthesis of 2,3,4- or 2,3,5-trisubstituted pyrroles has been achieved via [3,3] and [1,3] sigmatropic rearrangements of O-vinyl oximes, respectively. Iridium-catalyzed isomerization of easily prepared O-allyl oximes enables rapid access to O-vinyl oximes. The regioselectivity of pyrrole formation can be controlled by either the identity of the α-substituent or through the addition of an amine base. When enolization is favored, a [3,3] rearrangement followed by a Paal-Knorr cyclization provides a 2,3,4-trisubstituted pyrrole; when enolization is disfavored, a [1,3] rearrangement occurs prior to enolization to produce a 2,3,5-trisubstituted pyrrole after cyclization. Optimization and scope of the O-allyl oxime isomerization and subsequent pyrrole formation are discussed and mechanistic pathways are proposed. Conditions are provided for selecting either the [3,3] rearrangement or the [1,3] rearrangement product with β-ester O-allyl oxime substrates.

Aminosilanes in Organic Synthesis. Addition of Organocopper Reagents on γ-Bis(trimethylsilyl)amino-α-Acetylenic Amides, Esters and Ketones. Stereochemistry und Some Synthetic Uses

The stereochemical outcome of the carbocupration of γ-bis(trimethylsilyl)amino-α-acetylenic amide, esters and ketone was studied.A judicious choice of substrate, reagent and(or) reaction conditions allows to perform highly stereoselective cis or trans addition.The intermediate vinylic copper adducts, with (E) or (Z) configuration, react with electrophilic reagents to provide short routes to substituted pyrrolinones and pyrroles.Keywords: Silylamines, propargylamines, organocopper regaents, stereochemistry, nitrogen heterocycles.

SILYLAMINES IN ORGANIC SYNTHESIS : A NEW ACCESS TO FUNCTIONAL PYRROLES VIA ORGANOCUPRATES ADDITION ON METHYL-BIS(TRIMETHYLSILYL)AMINOMETHYLPROPIOLATE

Organocuprate addition reactions on methyl-bis(trimethylsilyl)aminomethylpropiolate lead to the formation of a Z-vinyl cuprate with a high stereoselectivity.Upon reaction of acid chloride, pyrroles are formed by a spontaneous intramolecular cyclisation of the intermediate Z-silylamino enone.Various functional substituted pyrroles can be obtained in one step by this route.