1003-90-3

Basic information

• Product Name: 2,3,4,5-TETRAMETHYLPYRROLE
• Synonyms: 2,3,4,5-TETRAMETHYLPYRROLE;2,3,4,5-tetramethyl-1H-pyrrole;2,3,4,5-TETRAMETHYLPYRROLE: TECH., 85%;1H-Pyrrole, 2,3,4,5-tetraMethyl-
• CAS NO: 1003-90-3
• Molecular Formula: C₈H₁₃N
• Molecular Weight: 123.2
• EINECS: 213-717-0
• Mol File: 1003-90-3.mol

Chemical Properties

• Melting Point: 107-110°C
• Boiling Point: 175.67°C (estimate)
• Flash Point: 83.1°C
• Appearance: /
• Density: 0.9098 (estimate)
• Vapor Pressure: 0.208mmHg at 25°C
• Refractive Index: 1.4844 (estimate)
• Sensitive: Air & Light Sensitive
• BRN: 107096
• CAS DataBase Reference: 2,3,4,5-TETRAMETHYLPYRROLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5-TETRAMETHYLPYRROLE(1003-90-3)
• EPA Substance Registry System: 2,3,4,5-TETRAMETHYLPYRROLE(1003-90-3)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 1003-90-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2,3,4,5-Tetramethylpyrrole is used as a key intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and medicinal compounds.
Used in Flavoring Additives for the Food Industry:
2,3,4,5-Tetramethylpyrrole is used as a flavoring additive in the food industry, enhancing the taste and aroma of various food products due to its strong odor.
Used in Polymer Production:
2,3,4,5-Tetramethylpyrrole is utilized in the production of polymers, playing a role in the creation of new materials with specific properties for various applications.
Used as a Reagent in Organic Chemistry Reactions:
2,3,4,5-Tetramethylpyrrole serves as a reagent in organic chemistry, facilitating various chemical reactions and processes in research and industrial settings.

InChI:InChI=1/C8H13N/c1-5-6(2)8(4)9-7(5)3/h9H,1-4H3

Upstream product

• 32990-59-3 2-ethyl-3,5-dimethyl-pyrrole 
• 141-52-6 sodium ethanolate 
• 19005-95-9 2,4,5-Trimethyl-3-acetyl-pyrrole 
• 124-41-4 sodium methylate 
• 2199-54-4 2,4,5-trimethyl-3-ethoxycarbonylpyrrole 
• 2436-79-5 diethyl 2,4-dimethylpyrrole-3,5-dicarboxylate 
• 3855-78-5 2,3,4-trimethyl-1H-pyrrole 
• 2199-41-9 2,3,5-trimethylpyrrole 
• 917-58-8 potassium ethoxide 
• 50-00-0 formaldehyd 
• 625-84-3 2,5-Dimethylpyrrole 
• 124-38-9 carbon dioxide 
• 67-56-1 methanol 
• 625-82-1 2,4-dimethyl-1H-pyrrole 

Downstream Products

• 111422-67-4 2,3,4,5-tetramethyl-2-(3-methylbuta-1,2-dienyl)-2H-pyrrole 
• 111422-79-8 2,4,5,6-tetramethyl-3-(2-methylprop-1-enyl)pyridine hydrochloride 
• 380609-03-0 [Hf(η(5)-NC4(CH3)4)(CH2C6H5)3] 
• 380609-01-8 [Ti(η(5)-NC4(CH3)4)(CH2C6H5)3] 
• 380609-02-9 [Zr(η(5)-NC4(CH3)4)(CH2C6H5)3] 
• 120892-95-7 1-acetyl-2,3,4,5-tetramethyl-pyrrole 

Relevant articles and documents

Iridium-catalyzed methylation of indoles and pyrroles using methanol as feedstock

Iridium-catalyzed methylation of indoles and pyrroles using methanol as the methylating agent was achieved. This transformation takes place via a borrowing hydrogen methodology under an air atmosphere, which constitutes a direct route to 3-methyl-indoles and methyl-pyrroles.

Catalytic methylation of C-H bonds using CO2 and H2

Formation of C-C bonds from CO2 is a much sought after reaction in organic synthesis. To date, other than C-H carboxylations using stoichiometric amounts of metals, base, or organometallic reagents, little is known about C-C bond formation. In fact, to the best of our knowledge no catalytic methylation of C-H bonds using CO2 and H2 has been reported. Described herein is the combination of CO2 and H2 for efficient methylation of carbon nucleophiles such as indoles, pyrroles, and electron-rich arenes. Comparison experiments which employ paraformaldehyde show similar reactivity for the CO2/H2 system. Capturing: Carbon dioxide in the presence of H2 is shown to be an efficient methylating reagent for carbon nucleophiles such as 2-substituted indoles, pyrroles, and electron-rich arenes. Experimental data support the formal capture of formaldehyde. acac=acetylacetonate, triphos=1,1,1-tris(diphenylphosphinomethyl)ethane.

Preparation method of monocyclic or polycyclic compound containing pyrrole ring

The invention discloses a preparation method of a monocyclic or polycyclic compound containing a pyrrole ring. An enamine compound is used as a raw material and is continuously subjected to diazotization, reduction and cyclization synthesis with a carbony

Electrochemical oxidation and EPR spectroscopy of radical cations of N-substituted 2,3,4,5-Tetramethylpyrroles

Electrochemical oxidation of 19 N-substituted 2,3,4,5-tetramethylpyrroles has been studied in acetonitrile and dichloromethane by means of slow cyclic voltammetry and coulometry. The first oxidation consumes one electron and occurs within the potential range 0.60-0.94 V in acetonitrile and 0.78-1.17 V in dichloromethane (vs. SCE). Twelve in situ generated primary radical cations were sufficiently stable at lowered temperature in dichloromethane for EPR measurement and showed well resolved HFS. The g-values (≈2.0026) and the coupling constants of 2,5-methyls (aH≈1.5 mT), 3,4-methyls (aH≈0.35 mT), and of the pyrrole nitrogen (aN≈0.42 mT) are very proximate for all 12 radical cations. It can be concluded, with support from quantum chemical calculations, that the odd electron is localised entirely on the pyrrole ring in the a2 HOMO of the parent molecule. Despite the odd electron distribution, the stability of the radical cations depends on the particular substituent attached to the pyrrole nitrogen. Acta Chemica Scandinavica 1998.

Intermediates in the Paal-Knorr Synthesis of Pyrroles

The mechanism of Paal-Knorr reaction between a 1,4-dicarbonyl compound and ammonia or a primary amine to form a pyrrole is explored.In aprotic solvents and in aqueous solutions near neutrality, d,l diastereomers of 3,4-dimethyl- and 3,4-diethyl-2,5-hexanediones (1r and 2r) formed pyrroles 1.3-57.0 times faster than the corresponding meso diastereomers (1m and 2m).This contradicts any intermediate, such as the enamine 15, which does not remain saturated at both the 3- and 4-positions through the rate-determining step.The demonstrated stereoisomeric difference in reactivity coupled with the following results support the hemiaminal (9) as the intermediate undergoing cyclization in the rate-limiting step of the Paal-Knorr reaction: (1) The reaction rate was adversely affected by increase in the size of the alkyl substituents on the dione. (2) Racemic 2,3-dimethyl-1,4-diphenyl-1,4-butanedione (3r) was more reactive toward ammonium acetate (2.2:1) and 2-aminoethanol (11.2:1) than the meso isomer (3m), ruling out the involvement of the less substituted enamine 14. (3) The relative rate of pyrrole formation of 1,4-diphenyl-1,4-butanedione (5) and its dimethoxy (6) and dinitro (7) derivatives (1:0.3:6) does not support cyclization of the imine (11) to the pyrrolinium ion (12). (4) The rates of reaction of 2,2,3,3-tetradeuterio-1,4-diphenyl-1,4-butanedione (5D) and perdeuterio-2,5-hexanedione (4D) were very close to those of unlabeled diketones, indicating the absence of a primary isotope effect in the reaction. (5) Neither the isomerization of the unreacted diastereomers of 1, 2, and 3 nor hydrogen exchange of 4D and 5D was detected during the reaction.

An Electron Spin Resonance Study of the Radical Cations of Pyrroles, Furans, and Thiophenes in Liquid Solution

Photolysis of alkylpyrroles in trifluoroacetic acid containing mercury(II) trifluoroacetate, alkylfurans in trifluoroacetic acid, or alkylthiophenes in sulphuric acid, induces oxidation to the corresponding radical cations.The e.s.r. spectra show that the electronic configuration is similar in all three species, the unpaired electron occupying the φA MO in which the heteroatom lies in a nodal plane.Photolysis of 2,6-dimethyl- and 2,6-diethyl-thiophene in trifluoroacetic acid containing mercury(II) trifluoroacetate, on the other hand, gave rise to spectra with a high g value (2.0062), showing hyperfine coupling to two non-equivalent pairs of alkyl groups in an unsymmetrical dimer.

A CRITICAL EVALUATION OF THE KNORR SYNTHESIS OF TRIFLUOROMETHYLPYRROLES AND THE REACTIVITY OF DIETHYL 4-TRIFLUOROMETHYL-2-METHYLPYRROLE-3,5-DICARBOXYLATE

β-Trifluoromethylpyrroles are readily obtained by the Knorr synthesis, but the procedure fails for the preparation of the α-isomers.The β-trifluoromethyl group reacts with alkoxide anions and is reduced with lithium aluminium hydride.

Alkylation process

Substituted pyrrole compounds, such as 3-ethyl-4-methyl-5-carbethoxy pyrrole, 2,4-dimethyl-3-acetyl pyrrole and 2-methyl-5-carboxy pyrrole-4-propionic acid diethyl ester, are alkylated in a single step by reaction with an aldehyde or ketone in the presence of both an acid condensing agent such as hydriodic acid and a compatible reducing agent such as metallic zinc or stannous chloride. Suitable carbonyl reactants include formaldehyde, paraldehyde, isobutyraldehyde, acetone, cyclohexanone and methyl-isobutyl ketone. This application is a continuation application of U.S. application Ser. No. 281,624 filed Aug. 18, 1972, now abandoned, which is a continuation-in-part application of U.S. application Ser. No. 832,001, filed June 10, 1969, now abandoned.