767-76-0

Basic information

• Product Name: 1,2,3,4,5-pentamethyl-1H-pyrrole
• Synonyms: 1,2,3,4,5-pentamethyl-1H-pyrrole
• CAS NO: 767-76-0
• Molecular Formula: C₉H₁₅N
• Molecular Weight: 137.2221
• EINECS: 212-188-3
• Mol File: 767-76-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 71 °C
• Boiling Point: 226°C at 760 mmHg
• Flash Point: 90.5°C
• Appearance: /
• Density: 0.88g/cm³
• Vapor Pressure: 0.126mmHg at 25°C
• Refractive Index: 1.485
• PKA: 0.86±0.70(Predicted)
• CAS DataBase Reference: 1,2,3,4,5-pentamethyl-1H-pyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,5-pentamethyl-1H-pyrrole(767-76-0)
• EPA Substance Registry System: 1,2,3,4,5-pentamethyl-1H-pyrrole(767-76-0)

Safety Data

• Hazardous Substances Data: 767-76-0(Hazardous Substances Data)

Usage

Description

1,2,3,4,5-pentamethyl-1H-pyrrole is a chemical compound characterized by the molecular formula C10H17N. It is a colorless liquid with a distinctive pungent odor and is insoluble in water. This versatile compound is recognized for its utility in various chemical applications, particularly in organic synthesis, pharmaceuticals, agrochemicals, and coordination chemistry.

Uses

Used in Organic Synthesis:
1,2,3,4,5-pentamethyl-1H-pyrrole serves as a fundamental building block in organic synthesis, playing a crucial role in the creation of a wide array of pharmaceuticals and agrochemicals. Its structural properties make it a valuable component in the development of new and innovative chemical compounds.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 1,2,3,4,5-pentamethyl-1H-pyrrole is utilized as a key intermediate in the synthesis of various drugs. Its ability to form stable complexes with metal ions also contributes to its potential use in medicinal chemistry, enhancing the effectiveness and properties of certain pharmaceuticals.
Used in Agrochemical Production:
Similarly, in agrochemicals, 1,2,3,4,5-pentamethyl-1H-pyrrole is employed as a precursor for the synthesis of pesticides and other agricultural chemicals. Its versatility allows for the development of products that can address a range of agricultural needs.
Used as a Solvent in Chemical Processes:
1,2,3,4,5-pentamethyl-1H-pyrrole has been studied for its potential as a solvent in various chemical processes. Its unique properties may offer advantages over traditional solvents, potentially leading to more efficient and environmentally friendly chemical reactions.
Used in Coordination Chemistry:
1,2,3,4,5-pentamethyl-1H-pyrrole's ability to form stable complexes with metal ions makes it a valuable asset in coordination chemistry. This feature can be harnessed to create new materials with specific properties or to improve existing ones, contributing to advances in various scientific and industrial fields.

InChI:InChI=1/C9H15N/c1-6-7(2)9(4)10(5)8(6)3/h1-5H3

Upstream product

• 28895-02-5 3,4-dimethyl-2,5-hexanedione 
• 74-89-5 methylamine 
• 28895-03-6 racem. 3,4-dimethyl-hexane-2,5-dione 
• 28895-02-5 meso-3,4-dimethyl-hexane-2,5-dione 

Relevant articles and documents

Molecular design using electrostatic interactions. Part 4: Synthesis and properties of flexible tetrapodand tetracations derived from naphthalene. Role of structured water in the electrostatic binding of polyanion guests: A model for interactions in biological systems

The 1,4,5,8-tetracations 5 and 11 have been prepared from 1,4,5,8-tetrakis(bromomethyl)naphthalene and 1,4,5,8-tetrakis(bromomethyl)-2,3,6,7-tetramethylnaphthalene, respectively by treatment with DABCO in acetonitrile. Their interactions with the benzene-1,2,4,5-tetracarboxylate and naphthalene-1,4,5,8-tetracarboxylate tetraanions in water were investigated by 1H NMR titration and both tetracations were found to have greater binding affinity to the benzene tetracarboxylate. Both also gave precipitates with ferricyanide but only the naphthalene tetracation 5 gave a precipitate with ferrocyanide. The X-ray structure of the crystalline ferricyanide tetracation 14 from tetramethylnaphthalene showed the methylDABCO cationic arms to be alternately above and below the naphthalene ring, which was itself distorted from the plane. The bound water in the non-charge-matched complex 14 appears to have a more intimate role in the crystal structure than does the bound water in the charge-matched ferricyanide 15 derived from 2,4,6-tris(DABCO-N-methyl)mesitylene tribromide which we reported previously. An analogy with interactions in biological receptors is made.

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.