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
• Article Data: 8

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

General Description

2,3,4,5-tetramethylpyrrole is a chemical compound with the molecular formula C9H13N. It is a colorless liquid at room temperature and is used in the synthesis of pharmaceuticals and organic compounds. Tetramethylpyrrole is a derivative of pyrrole, a five-membered aromatic ring with one nitrogen atom. It is known for its strong odor and is used as a flavoring additive in the food industry. Tetramethylpyrrole is also used in the production of polymers and as a reagent in organic chemistry reactions. It is important to handle tetramethylpyrrole with caution as it is flammable and may cause skin and eye irritation upon contact.

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

Upstream product

• 2199-41-9 2,3,5-trimethylpyrrole 
• 50-00-0 formaldehyd 
• 917-58-8 potassium ethoxide 
• 124-41-4 sodium methylate 
• 3855-78-5 2,3,4-trimethyl-1H-pyrrole 
• 32990-59-3 2-ethyl-3,5-dimethyl-pyrrole 
• 141-52-6 sodium ethanolate 
• 27226-50-2 3,4,5-trimethyl-1H-pyrrole-2-carbaldehyde 
• 2199-54-4 2,4,5-trimethyl-3-ethoxycarbonylpyrrole 
• 17120-26-2 4-formyl-3,5-dimethyl-pyrrole-2-carboxylic acid 
• 2199-64-6 ethyl 3,5-dimethyl-4-formyl-1H-pyrrole-2-carboxylate 
• 2534-93-2 3,5,3',5'-tetramethyl-1H,2'H-2,2'-methanylylidene-bis-pyrrole 
• 28895-02-5 3,4-dimethyl-2,5-hexanedione 
• 861591-64-2 1,1-bis-(5-acetyl-2,4-dimethyl-pyrrol-3-yl)-ethane 

Downstream Products

• 120892-95-7 1-acetyl-2,3,4,5-tetramethyl-pyrrole 
• 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] 

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.

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

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.