20282-39-7

Basic information

• Product Name: 2,5-DIMETHYL-1-PROPYL-1H-PYRROLE
• Synonyms: Pyrrole,2,5-dimethyl-1-propyl- (8CI); 2,5-Dimethyl-1-propylpyrrole
• CAS NO: 20282-39-7
• Molecular Formula: C₉H₁₅N
• Molecular Weight: 137.22
• Mol File: 20282-39-7.mol

Chemical Properties

• Boiling Point: 205.1°Cat760mmHg
• Flash Point: 77.9°C
• Appearance: /
• Density: 0.87g/cm³
• Vapor Pressure: 0.364mmHg at 25°C
• Refractive Index: 1.483
• PKA: -0.26±0.70(Predicted)
• CAS DataBase Reference: 2,5-DIMETHYL-1-PROPYL-1H-PYRROLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIMETHYL-1-PROPYL-1H-PYRROLE(20282-39-7)
• EPA Substance Registry System: 2,5-DIMETHYL-1-PROPYL-1H-PYRROLE(20282-39-7)

Safety Data

• Hazardous Substances Data: 20282-39-7(Hazardous Substances Data)

Usage

Structure

A pyrrole compound with two methyl groups and one propyl group attached to the nitrogen atom

Aromatic properties

Pyrrole compounds are known for their aromatic properties

Common uses

Production of pharmaceuticals, agrochemicals, and materials science

Potential applications

May have potential applications in various industries due to its unique structure and reactivity

Further research needed

Further research and studies may be needed to explore its potential uses and properties.

InChI:InChI=1/C9H15N/c1-4-7-10-8(2)5-6-9(10)3/h5-6H,4,7H2,1-3H3

Upstream product

• 107-10-8 propylamine 
• 110-13-4 2,5-hexanedione 
• 109-49-9 5-Hexen-2-one 
• 108-03-2 1-Nitropropane 
• 71-23-8 propan-1-ol 
• 2935-44-6 hexane-2,5-diol 

Relevant articles and documents

Layered zirconium phosphate and phosphonate as heterogeneous catalyst in the preparation of pyrroles

Pyrroles may be prepared by condensation of alkyl and aryl amines and 1,4-diketones (Paal-Knorr reaction) under potassium exchanged layered Zirconium phosphate and zirconium sulfophenyl phosphonate catalyst in solvent free conditions.

Fe3+-montmorillonite as effective, recyclable catalyst for Paal-Knorr pyrrole synthesis under mild conditions

Fe3+-montmorillonite clay catalyst was used for the first time for pyrroles preparation by Paal-Knorr condensation. The features of this catalytic system are improved yields, mild conditions, a simple procedure, and high catalytic efficiency. The catalyst could be easily recycled and reused for three times without visible losing of activity. Copyright Taylor & Francis, Inc.

Spectroscopic Study of Some New N-Aryl Pyrroles

A series of new 2,5-dimethyl-N-substituted pyrroles (I) were obtained by condensation of 2,5-hexanedione with different amines.The UV data show that about 11.7percent of the total electronic density of the nitrogen of pyrrole ring is conjugated with the aryl group.A correlation between the UV and NMR results has been established, and the mass spectra of these derivatives have also been measured and discussed.

One-pot synthesis of N-substituted pyrroles catalyzed by polystyrene-supported aluminum chloride as a reusable heterogeneous Lewis acid catalyst

A convenient and efficient procedure is presented for the one-pot synthesis of N-substituted pyrroles by condensation of 2,5-hexandione and amines or diamines in the presence of cross-linked polystyrene-supported aluminum chloride (PS/AlCl3) as a highly active and reusable heterogeneous Lewis acid catalyst. This polymeric solid acid catalyst is stable and can be easily recovered and reused without appreciable change in its efficiency.

Pyrrole synthesis in ionic liquids by Paal-Knorr condensation under mild conditions

Paal-Knorr condensation of 2,5-hexandione with primary amines was successfully carried out in ionic liquids. Through investigating different ionic liquids, different reaction times, the reaction, using ionic liquids as solvent, exhibited simple product isolation procedure, improved yields and exclusive selectivity and the mild conditions and the avoidance of using toxic catalysts are also its special features. Recovery and reuse of ionic liquid are also satisfactory.

Hexafluoroisopropanol as solvent and promotor in the Paal-Knorr synthesis of N-substituted diaryl pyrroles

An additive-free synthesis of challenging N-substituted aryl pyrroles from the often poorly soluble corresponding 1,4-diketones by means of the Paal-Knorr pyrrole synthesis is reported, which makes use of the unique properties of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a solvent and reaction promotor. Our procedure offers simple execution and purification as well as easy scale-up and can be applied in the Paal-Knorr synthesis of a large number of structurally diverse pyrroles including the synthetically challenging tetra- and penta-substituted pyrroles in moderate to excellent yields. HFIP can also be used as solvent in the Paal-Knorr synthesis of furans and thiophenes; however, the solvent effect is more pronounced in synthesis of pyrroles.

Grinding solvent-free paal-knorr pyrrole synthesis on smectites as recyclable and green catalysts

An environmentally benign method for the synthesis of N-substituted pyrroles from one-pot solvent-free condensation reaction of 2,5-hexanedione with various primary amines (Paal-Knorr pyrrole synthesis) on smectite clays as green and reusable heterogeneous Lewis acid catalysts is presented. The use of nontoxic, inexpensive, easily available and reusable catalysts under solvent-free conditions make this protocol practical, environmentally friendly and economically attractive.

Acceptorless Dehydrogenative Coupling Using Ammonia: Direct Synthesis of N-Heteroaromatics from Diols Catalyzed by Ruthenium

The synthesis of N-heteroaromatic compounds via an acceptorless dehydrogenative coupling process involving direct use of ammonia as the nitrogen source was explored. We report the synthesis of pyrazine derivatives from 1,2-diols and the synthesis of N-substituted pyrroles by a multicomponent dehydrogenative coupling of 1,4-diols and primary alcohols with ammonia. The acridine-based Ru-pincer complex 1 is an effective catalyst for these transformations, in which the acridine backbone is converted to an anionic dearomatized PNP-pincer ligand framework.

One-pot synthesis of: N -substituted pyrroles from nitro compounds and 2,5-hexadione over a heterogeneous cobalt catalyst

In this study, the one-pot heterocyclization of nitro compounds with 2,5-hexadione was studied for the synthesis of N-substituted pyrroles via a Paal-Knorr condensation process. The heterogeneous cobalt-nitrogen catalyst (Co-Nx/C-800-AT) was found to be active for this reaction with formic acid. Formic acid served as a hydrogen donor for the transfer hydrogenation, and also acted as an acid catalyst. More importantly, this method was tolerant of other functional groups, and hence various N-substituted pyrroles were produced with good to excellent yields. The Co-Nx/C-800-AT catalyst was highly stable, and could be reused several times without loss of its catalytic activity.

Efficient synthesis of substituted pyrroles through Pd(OCOCF3)2-catalyzed reaction of 5-hexen-2-one with primary amines

An efficient and facile Pd(OCOCF3)2-catalyzed one-pot cascade protocol has been developed for the synthesis of multiple substituted pyrroles in good to excellent yields. Unlike the reported method starting from the 2-alkenal-1,3-carbonyl compounds, the process utilizes the less reactive 5-hexen-2-one and the method has great potential as a complement to the current developed methods.