96-54-8

Basic information

• Product Name: N-Methyl pyrrole
• Synonyms: N-Methylpyrrol;Pyrrole, 1-methyl-;pyrrole,1-methyl-;1-methyl-1h-pyrrole;1-METHYLPYRROLE;1-METHYLPYRROLE 99+%;N-Methylpyrrole,99%;METHYLPYRROLE
• CAS NO: 96-54-8
• Molecular Formula: C₅H₇N
• Molecular Weight: 81.12
• EINECS: 202-513-7
• Product Categories: Functional Materials;Pyrroles (for Conduting Polymer Research);Reagents for Conducting Polymer Research;pyrrole;Building Blocks;Heterocyclic Building Blocks;Pyrroles;Imidazoles
• Mol File: 96-54-8.mol

Chemical Properties

• Melting Point: −57 °C(lit.)
• Boiling Point: 112-113 °C(lit.)
• Flash Point: 59 °F
• Appearance: yellow-brown/liquid
• Density: 0.914 g/mL at 25 °C(lit.)
• Vapor Density: 2.8 (vs air)
• Vapor Pressure: 15 mm Hg ( 20.2 °C)
• Refractive Index: n20/D 1.489
• Storage Temp.: 2-8°C
• Solubility: 13g/l
• PKA: -2.80±0.70(Predicted)
• Explosive Limit: 1.4-8.5%(V)
• Water Solubility: Soluble in organic solvents such as alcohol and so on, but insoluble in water.
• BRN: 104181
• CAS DataBase Reference: N-Methyl pyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl pyrrole(96-54-8)
• EPA Substance Registry System: N-Methyl pyrrole(96-54-8)

Safety Data

• Hazard Codes: F,Xi,Xn
• Statements: 11-36/37/38-37/38-22
• Safety Statements: 16-26-36-37-25-23
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• RTECS: UX9640000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 96-54-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-Methyl pyrrole is used as an organic synthetic material for its versatile reactivity and ability to form a wide range of chemical compounds. Its presence in various molecular structures makes it a key component in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
N-Methyl pyrrole is used as a pharmaceutical intermediate for its potential role in the development of new drugs. Its unique chemical properties allow it to be incorporated into medicinal compounds, potentially leading to the creation of novel therapeutic agents with improved efficacy and selectivity.
Used in Medicine:
N-Methyl pyrrole is widely used in medicine due to its diverse applications in drug development and synthesis. Its presence in various pharmaceutical compounds contributes to the treatment and management of a range of medical conditions, highlighting its importance in the healthcare sector.

Hazard

Flammable, dangerous fire risk.

Purification Methods

Dry N-methylpyrrole with CaSO4, then fractionally distil it from KOH immediately before use. [Beilstein 20 III/IV 2080, 20/5 V 8.]

InChI:InChI=1/C5H7N/c1-6-4-2-3-5-6/h2-5H,1H3

Upstream product

• 120-94-5 1-Methylpyrrolidine 
• 110-00-9 furan 
• 74-89-5 methylamine 
• 109-97-7 pyrrole 
• 21898-43-1 2-(1-methyl-1H-pyrrol-2-yl)-2-oxoacetic acid 
• 69309-33-7 1,4-bis-(dimethylamino)-1,3-butadiene 
• 16199-06-7 potassium pyrrolide 
• 74-88-4 methyl iodide 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 593-51-1 methylamine hydrochloride 
• 7223-38-3 N,N-Dimethylpropargylamin 
• 593-53-3 Methyl fluoride 
• 64710-12-9 dimethylfluoronium ion 
• 333-27-7 methyl trifluoromethanesulfonate 

Downstream Products

• 6974-95-4 2-(N-morpholinylmethyl)-1-methylpyrrole 
• 21898-59-9 1-methylpyrrole-2-acetic acid 
• 49669-45-6 ethyl (1-methyl-1H-pyrrol-2-yl)acetate 
• 26052-09-5 N-methyl(1-methyl-1H-pyrrol-2-yl)methylanamine 
• 56139-76-5 2-(N,N-dimethylaminomethyl)-1-methylpyrrole 
• 24460-50-2 1-(1-methyl-1H-pyrrol-2-yl)butan-2-one 
• 1192-58-1 N-methylpyrrole aldehyde 
• 69217-15-8 (E)-1-methyl-2-(phenyldiazenyl)-1H-pyrrole 
• 103503-90-8 1-methyl-2,5-bis-(3-oxo-3-phenyl-propyl)-pyrrole 
• 56453-98-6 N-methyl-2-((4'-nitrophenyl)diazenyl)-pyrrole 
• 766-95-0 2,5-diethyl-pyrrole 
• 145497-60-5 1-methyl-2-p-tolylazo-pyrrole 
• 932-16-1 N-methyl-2-acetylpyrrole 
• 37496-06-3 2-benzoyl-1-methyl-1H-pyrrole 

Relevant articles and documents

Structural reorganization of allyl isothiocyanate into pyrrole ring under superbase: A straightforward access to NH-2-(Alkylsulfanyl)-1H-pyrroles and N-Alkyl-2-(alkylsulfanyl)-1H-pyrroles

A novel and facile synthetic route to NH-2-(alkylsulfanyl)-1H-pyrroles and N-alkyl-2-(alkylsulfanyl)-1H-pyrroles is reported. This was achieved by deprotonation of allyl isothiocyanate with the superbasic pair lithium diisopropylamide and potassium tert-butoxide (1:1 molar mixture), followed by intramolecular ring closure, deprotonation of cyclic anion with a second equivalent of the superbase, and final sequential N-protolysis/S-alkylation or N,S-dialkylation of the formed N,S-centered pyrrol-2-ylsulfide dianion. Georg Thieme Verlag Stuttgart · New York.

Copper-Catalyzed Synthesis of Indolyl Benzo[b]carbazoles and Their Photoluminescence Property

A copper-catalyzed cascade cyclization of dihydroisobenzofurans with indoles for the rapid construction of indoly benzo[b]carbazoles has been reported, providing the desired products in moderate to good yields under mild conditions along with a broad substrate scope and good functional group tolerance. The photoluminescence property of these indoly benzo[b]carbazoles has also been investigated.

Anti-inflammatory COX/LOX inhibitor, and preparation method and application thereof

The invention provides an anti-inflammatory COX/LOX inhibitor, and a preparation method and an application thereof. The inhibitor is a compound represented by formula I, or a pharmaceutically acceptable salt thereof. The novel anti-inflammatory COX/LOX inhibitor can significantly reduce the ear swelling degree of mice in an administrated group in xylene-induced ear swelling test, so the compound has an anti-inflammatory effect, and the anti-inflammatory effect of the compound is equivalent with that of aspirin; and additionally, pharmacological tests show that the compound has small irritationto the gastrointestinal tract. The preparation method of the novel anti-inflammatory COX/LOX inhibitor has the advantages of simplicity, easiness in operation, and effectiveness in the reduction of the production cost to realize industrial production.

Alkylation method for nitrogen-hydrogen containing compounds and application thereof

The invention discloses an alkylation method for nitrogen-hydrogen containing compounds and an application thereof, belonging to the technical field of synthesis of organic compounds. The invention provides a series of methods for a nitrogen alkylation reaction of N-H containing heterocyclic compounds (II) with N,N-dimethylformamide dialkyl acetal as an alkyl source under the condition of no participation of metals, and a product with a hydrogen atom on a nitrogen atom substituted by R1 is obtained. The method provided by the invention has the advantages of highly-efficient reaction, high yield, simple treatment after the reaction, simple and convenient operation, mild reaction conditions, no participation of the metals, high tolerance of functional groups of a reaction substrate, wide range and easy preparation of the substrate, high reaction efficiency after amplification of the reaction, and applicability to large-scale industrial production.

Synthesis method of N-methylpyrrole

The invention discloses a synthesis method of N-methylpyrrole. The method comprises the step of enabling butanedial and methylamine to be subjected to a heating reaction under the alkaline condition so as to obtain the N-methylpyrrole. Compared with the prior art, the synthesis method provided by the invention has the characteristics of being short in reaction route, low in cost, relative mild inreaction condition, high in reaction yield, and the like; the method is simple to operate and convenient in aftertreatment, thus having industrial application prospect.

Selective catalytic transfer dehydrogenation of alkanes and heterocycles by an iridium pincer complex

Catalytic alkane dehydrogenation is a reaction with tremendous potential for application. We describe a highly active PSCOP-pincer iridium catalyst for transfer dehydrogenation of cyclic and linear alkanes. The dehydrogenation of linear alkanes occurs under relatively mild conditions with high regioselectivity for a-olefin formation. In addition, the catalyst system is very effective in the dehydrogenation of heterocycles to form heteroarenes and olefinic products.

Green N-methylation of electron deficient pyrroles with dimethylcarbonate

The N-methylation of electron-deficient pyrroles was affected using dimethyl carbonate in the presence of DMF and catalytic DABCO. This alkylation methodology has proven useful for the alkylation of a variety of pyrroles in 72-98% yields and is considered to be green chemistry relative to the more common use of methyl halides or dimethyl sulfate.

Incomparably easy migration of functionalized enol substituent in pyrrole ring

Functionalized pyrrolebvbΕ enols, 2-(1-hydroxy-2.2-dicyanoethenyl)-1- methylpyrroles, at heating (75-135°C) unexpectedly readily rearranged in high yield into 3-isomers. Evidently the migration of the enol fragment involves a mesomeric zwitterion formed as a result of an intra- and intermolecular autoprotonation of the pyrrole ring by the acidic enol hydroxy group. Under similar conditions no migration of the ethenyl moiety occurred in 2-(1-hydroxy-2-carbamoyl-2-cyanoethenyl)-1-methylpyrroles. The quantum-chemical calculations (MP2/6-311G**) show a clear-cut distinction in the relative stability of 2- and 3-isomers of 1H- and 1- methylhydroxyethenylpyrroles: in the former case the 2-isomer is more stable, whereas in the 1-methyl-substituted compound, the 3-isomer.

Superbase-promoted direct N-carbonylation of pyrrole with carbonic acid diesters

Carbonic acid diesters have been investigated as carbonylating agents in the direct reaction with pyrrole (HetNH). In the presence of superbases (DBU, P1-t-Bu, BTPP) as catalysts, the heteroaromatic substrate can be N-carbonylated by direct reaction with carbonic acid diesters under not-severe experimental conditions. The carbonylation reaction makes accessible pyrrole N-carbonyl derivatives (HetNC(O)OR, (HetN)2CO) selectively through a simple straightforward way, which offers a safe eco-friendly alternative to the traditional synthetic methods based on hazardous phosgene or phosgene-derivatives.

Potassium carbonate as a base for the N-alkylation of indole and pyrrole in ionic liquids

The methodology for the N-alkylation of indole and pyrrole using potassium carbonate in 1-n-butyl-3-methylimidazolium tetrafluoroborate [bmim][BF4] as the sustainable reaction media with acetonitrile as the cosolvent is described herein. Our approach provides good yields with alkyl halides as well as sulfonates as the electrophiles. Cesium carbonate was also found to be a consistent base in the N-alkylation. The proposed methodology is simple and mild with easy workup.