2199-59-9

Basic information

• Product Name: Ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate
• Synonyms: Ethyl 2,4-dimethyl-5-formylpyrrole-3-carboxylate;5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl este;Ethyl 2,4-dimethyl-5-formyl-1H-pyrrole-3-carboxylate 97%;3,5-Dimethyl-4-(ethoxycarbonyl)-1H-pyrrole-2-carboxaldehyde;Ethyl 5-ForMyl-2,4-diMethylpyrrole-3-carboxylate;3,5-Dimethyl-4-(ethoxycarbonyl)-1H-pyrrole-2-carboxaldehyde, 2,4-Dimethyl-3-(ethoxycarbonyl)-5-formyl-1H-pyrrole;Ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate 5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester;Ethyl 5-Formyl-2,4-dimethyl-3-pyrrolecarboxylate
• CAS NO: 2199-59-9
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.22
• EINECS: 1806241-263-5
• Product Categories: Pharmaceutial intermediates;pharmacetical;Pyrrole&Pyrrolidine&Pyrroline;Intermediate of sunitinib malate;Sunitinib Intermediate
• Mol File: 2199-59-9.mol
• Article Data: 41

Chemical Properties

• Melting Point: 164.0 to 168.0 °C
• Boiling Point: 358.4 °C at 760 mmHg
• Flash Point: 170.5 °C
• Appearance: /Solid
• Density: 1.173 g/cm³
• Vapor Pressure: 2.56E-05mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 14.65±0.50(Predicted)
• CAS DataBase Reference: Ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate(2199-59-9)
• EPA Substance Registry System: Ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate(2199-59-9)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 2199-59-9(Hazardous Substances Data)

Usage

Chemical Properties

Brown crystals

Uses

5-ForMyl-2,4-diMethyl-1H-pyrrole-3-carboxylic Acid Ethyl Ester is used as an intermediate in the synthesis of receptor tyrosine kinase (RTK) inhibitors and their metabolites.

InChI:InChI=1/C10H13NO3/c1-4-14-10(13)9-6(2)8(5-12)11-7(9)3/h5,11H,4H2,1-3H3

Upstream product

• 86770-31-2 2-tert-butyl 4-ethyl 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate 
• 122-51-0 orthoformic acid triethyl ester 
• 2199-51-1 2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 5430-82-0 5-hydroxymethyl-2,4-dimethyl-pyrrole-3-carboxylic acid ethyl ester 
• 2436-79-5 diethyl 2,4-dimethylpyrrole-3,5-dicarboxylate 
• 64-17-5 ethanol 
• 58298-68-3 methyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate 
• 253870-02-9 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid 
• 141-97-9 ethyl acetoacetate 
• 5442-91-1 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylic acid 4-ethyl ester 
• 149-73-5 trimethyl orthoformate 
• 93-61-8 N-methyl-N-phenylformamide 
• 10025-87-3 trichlorophosphate 

Downstream Products

• 253870-02-9 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid 
• 341031-54-7 sunitinib malate 

Relevant articles and documents

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Conformationally Induced Off-On Cell Membrane Chemosensor Targeting Receptor Protein-Tyrosine Kinases for in Vivo and in Vitro Fluorescence Imaging of Cancers

Molecules capable of monitoring receptor protein-tyrosine kinase expression could potentially serve as useful tools for cancer diagnosis due to the overexpression of tyrosine kinases during tumor growth and metastasis. In this work, a conformationally induced "off-on" tyrosine kinase cell membrane fluorescent sensor (SP1) was designed and evaluated for the detection and imaging of receptor protein-tyrosine kinases in vivo and in vitro. SP1 consists of sunitinib and pyrene linked via hexamethylenediamine and displays quenched fluorescence as a dimer. The fluorescence of SP1 is restored in the presence of receptor protein-tyrosine kinases upon strong interaction with SP1 at the target terminal. The unique signal response mechanism enables SP1 use for fluorescence microscopy imaging of receptor protein-tyrosine kinases in the cell membranes of living cells, allowing for the rapid differentiation of cancer cells from normal cells. SP1 can be used to visualize the chick embryo chorioallantoic membrane and mouse model tumors, suggesting its possible application for early cancer diagnosis.

Antimicrobial and antiproliferative study of chalcone clubbed 2,4-dimethylpyrrole-3-carboxamide derivatives: Synthesis and in vitro evaluation

The presented study explores the anticancer potency of a novel series of chalcone clubbed 2,4-dimethyl-1H-pyrrole-3-carboxamide derivatives. In vitro antimicrobial screening concluded that five compounds are potential against Candida albicans having inhibition of growth in the range of 46.38%–73.05% against at the concentration of 32 μg/mL. The antiproliferative screening against 60 cancer cell lines revealed that seven compounds have great potential against the various types of cancer cell lines with inhibition of growth in the range of 41%–71%. The structure–activity relationship study concluded that the hydrazide bond is more significant than the carboxamide bond. In silico study of highly potential derivatives obeys each parameter of Lipinski rule of five and qualified drug-likeness behavior. The presented pyrrole-chalcone template delivered various candidates as anticancer agents, and those could be a potential scaffold to develop the new anticancer drug.

IBX-TfOH mediated oxidation of alcohols to aldehydes and ketones under mild reaction conditions

An efficient, practical and facile procedure has been developed for the oxidation of primary and secondary alcohols using IBX-TfOH catalytic system in 1,4-dioxane at ambient temperature. The reaction affords quantitative yields of the corresponding carbonyl compounds without the formation of over oxidized products. The present synthetic protocol is compatible with a variety of substrates having arene, heteroarene and alkene functionalities. The developed synthetic protocol can be used for higher scale reactions as evident by the oxidation of alcohol at 1 g scale in higher yields by a simple filtration process.

Preparation method of sunitinib intermediate

The invention discloses a preparation method of a sunitinib intermediate. The method includes the following steps of 1, synthesis of 2, 4-dimethylpyrrole-3, 5-diethyl dicarboxylate, 2, synthesis of 4-ethoxycarbonyl-3, 5-dimethylpyrrole-2-carboxylic acid, 3, synthesis of 2, 4-dimethyl-3-ethyl pyrrole-2-carboxylate, 4, synthesis of 2, 4-dimethyl-5-aldehyde-1H-pyrrole-3-ethyl formate, and 5, synthesis of 2,4-dimethyl-5-aldehyde-1H-pyrrole-3-carboxylic acid. The method has the advantages that the raw materials are cheap, the environmental pollution is small, the industrial production is easy to achieve, the processing steps are fewer, the operation is simple, the reaction yield is very high, the mass production of enterprise is facilitated, and application and popularization are facilitated.