14745-84-7

Basic information

• Product Name: N,N-dimethyl-1-(1H-pyrrol-2-yl)methanamine
• Synonyms: N,N-dimethyl-1-(1H-pyrrol-2-yl)methanamine;2-[(DiMethylaMino)Methyl]pyrrole;1H-Pyrrole-2-methanamine, N,N-dimethyl-;dimethyl-(1H-pyrrol-2-ylmethyl)amine;N,N-Dimethyl(1H-pyrrol-2-yl)methanamine
• CAS NO: 14745-84-7
• Molecular Formula: C₇H₁₂N₂
• Molecular Weight: 124.19
• Mol File: 14745-84-7.mol

Chemical Properties

• Melting Point: 64 °C
• Boiling Point: 181.3°C at 760 mmHg
• Flash Point: 63.5°C
• Appearance: /
• Density: 0.998g/cm³
• Vapor Pressure: 0.858mmHg at 25°C
• Refractive Index: 1.533
• Storage Temp.: 2-8°C
• PKA: 16.96±0.50(Predicted)
• CAS DataBase Reference: N,N-dimethyl-1-(1H-pyrrol-2-yl)methanamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-dimethyl-1-(1H-pyrrol-2-yl)methanamine(14745-84-7)
• EPA Substance Registry System: N,N-dimethyl-1-(1H-pyrrol-2-yl)methanamine(14745-84-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 14745-84-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
N,N-dimethyl-1-(1H-pyrrol-2-yl)methanamine is used as a reagent in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure and properties make it a valuable component in the development of new and effective compounds for these industries.
Used in Organic Synthesis:
N,N-dimethyl-1-(1H-pyrrol-2-yl)methanamine is also used in the synthesis of other nitrogen-containing compounds, contributing to the creation of a wide range of organic molecules with diverse applications in various fields.

InChI:InChI=1/C7H12N2/c1-9(2)6-7-4-3-5-8-7/h3-5,8H,6H2,1-2H3

Upstream product

• 109-97-7 pyrrole 
• 50-00-0 formaldehyd 
• 506-59-2 N,N-dimethylammonium chloride 
• 469-61-4 alpha-cedrene 
• 7309-47-9 bis(N-pyrrolidinyl)methane 
• 51-80-9 bis-(dimethylamino)methane 
• 7732-18-5 water 
• 33797-51-2 eschenmoser's salt 
• 75866-92-1 N-((1H-pyrrol-2-yl)methylene)-N-methylmethanaminium hydrogen chloride 
• 78307-76-3 N,N-dimethyl-1H-pyrrol-1-amine 
• 124-41-4 sodium methylate 
• 925-90-6 ethylmagnesium bromide 
• 19611-54-2 6-dimethylamino-1-azafulvene 

Downstream Products

• 99185-44-1 2-(phenyldiazenyl)-1H-pyrrole 
• 101-60-0 porphyrin 
• 50551-29-6 2-pyrroleacetonitrile 
• 2683-84-3 Chlorin 
• 148103-72-4 2-(phenylthiomethyl)pyrrole 
• 50-00-0 formaldehyd 
• 62-75-9 N-Nitrosodimethylamine 
• 74230-05-0 maleimidemonooxime 
• 67883-10-7 trans-iso-Bacteriochlorin 
• 148103-71-3 2-Benzenesulfinylmethyl-1H-pyrrole 
• 860362-26-1 4-methylpyrrolo[3,2-c]pyridine 
• 860721-07-9 4-phenyl-6,7-dihydro-1H-pyrrolo[3,2-c]pyridine 
• 855263-47-7 N-(2-pyrrol-2-yl-ethyl)-benzamide 

Relevant articles and documents

Nickel(II) and Palladium(II) Complexes Bearing an Unsymmetrical Pyrrole-Based PNN Pincer and Their Norbornene Polymerization Behaviors versus the Symmetrical NNN and PNP Pincers

Unsymmetrical pincers have been shown to be better than the corresponding symmetrical pincers in several catalysis reactions. A new unsymmetrical PNN propincer, 2-(3,5-dimethylpyrazolylmethyl)-5-(diphenylphosphinomethyl)pyrrole (1), was synthesized from pyrrole through Mannich bases in a good yield. In addition, the new byproduct 2-(3,5-dimethylpyrazolylmethyl)-5-(dimethylaminomethyl)-N-(hydroxymethyl)pyrrole was also isolated. The reaction of 1 with [PdCl2(PhCN)2] and Et3N in toluene yielded [PdCl{C4H2N-2-(CH2Me2pz)-5-(CH2PPh2)-κ3P,N,N}] (2). The analogous reaction between 1 and [NiCl2(DME)] or NiX2 (X = Br, I) in the presence of NEt3 in acetonitrile afforded [NiX{C4H2N-2-(CH2Me2pz)-5-(CH2PPh2)-κ3P,N,N}] (3; X = Cl, Br, I). All complexes were structurally characterized. The norbornene polymerization behaviors of the unsymmetrical pincer complexes 2 and 3 in the presence of MMAO or EtAlCl2 were compared with those of the symmetrical pincer complexes chloro[2,5-bis(3,5-dimethylpyrazolylmethyl)pyrrolido]palladium(II) (NNN), chloro[2,5-bis(diphenylphosphinomethyl)pyrrolido]palladium(II), and chloro[2,5-bis(diphenylphosphinomethyl)pyrrolido]nickel(II) (PNP) at different temperatures. The PNN and NNN complexes exhibited far greater activity on the order of 107 g of PNB/mol/h, with quantitative yields in some cases, in comparison to the PNP pincer palladium and nickel complexes. This trend was also supported by the iPr group substituted PNP nickel and palladium pincer complexes. These polymerization behaviors are explained using steric crowding around the metal atom with the support of NMR studies and suggested that the activity increases as the Npyrazole donor increases. Polymers were characterized by 1H NMR, IR, TGA, and powder XRD methods.

Directed Aminomethylation of Pyrrole, Indole, and Carbazole with N,N,N′,N′-Tetramethylmethanediamine

Catalytic aminomethylation of pyrrole and indole with N,N,N′,N′-tetramethylmethanediamine in the presence of 5 mol % of ZrOCl2·8H2O proceeds selectively at the positions 2, 5 of pyrrole and 1, 3 of indole. Carbazole under the same conditions affords 3-formyl-9-aminomethyl derivative. The reaction in the presence of 5 mol % of K2CO3 occurs as monoaminomethylation: for pyrrole at the position 2, for indole at the position 3, and for carbazole at the nitrogen atom of the substrate. Water-soluble 1,1′-(1H-pyrrole-2,5-diyl)bis(N,N-dimethylmethanamine) exhibits a fungistatic activity with respect to phytopathogenic fungi Rhizoctonia solani.

Mild microwave-assisted synthesis of dipyrromethanes and their analogues

The Mannich reaction between pyrroles or indoles and Eschenmoser's salt (dimethylmethylideneammonium iodide) forms N,N-dimethylamino-methylated derivatives in good to excellent yields. The reaction is highly regioselective, and for pyrroles both 2-and 3-s

The behavior of pyrrolyl ligands within the rare-earth metal alkyl complexes. Insertion of CN and CO double bonds into Ln-σ-C bonds

This paper presents some unusual reactions of lanthanide tris(alkyl)s or lanthanide mono-Cp′ (Cp′ = (C5Me4)SiMe 3) bis(alkyl)s with pyrrolyl ligands, and the η5- or η1-coordination mode of the pyrroly

AMINO ALCOHOL DERIVATIVE OR PHOSPHONIC ACID DERIVATIVE AND MEDICINAL COMPOSITION CONTAINING THESE

The present invention relates to amino alcohol derivatives or phosphonic acid derivatives having excellent immunosuppressive activity, pharmacologically acceptable salts thereof or pharmacologically acceptable esters thereof, and to pharmaceutical compositions comprising said compounds as an active ingredient: [wherein, ???R1 and R2 each represent a hydrogen atom, or a protecting group of the amino group; ???R3 represents a hydrogen atom, or a protecting group of the hydroxyl group; ???R4 represents a lower alkyl group; ???n represents an integer of from 1 to 6; ???X represents an oxygen atom or a nitrogen atom unsubstituted or substituted with a lower alkyl group or the like; ???Y represents an ethylene group; ???Z represents a C1-C10 alkylene group; ???R5 represents an aryl group, or an aryl group substituted with substituents; ???R6 and R7 each represents a hydrogen atom; provided that when R5 represents a hydrogen atom, then Z represents a group other than a single bond or a straight chain C1-C10 alkylene group] .

Substituted thiazoles as immunoregulants

Thiazole derivatives have been made, for example, by reacting a 2-aryl-2,2-dialkoxyethylamine with an appropriately substituted aryl acetyl halide followed by treating the resulting amide with diphosphoryl pentasulfide. The thiazole derivatives are found to be effective immunoregulants.

Mannich Reactions of Nucleophilic Aromatic Compounds involving Aminals and α-Amino Ethers activated by Chlorosilane Derivatives; Catalysis by Chlorotrimethylsilane

Aminals and α-amino ethers afford N,N-dialkylmethyleneammonium salts by reaction with dichloro(dimethyl)- and trichloro(methyl)-silanes, but whereas chlorotrimethylsilane interacts with α-amino ethers to yield iminium salts, the reaction of the latter silane with aminals does not; in situ Mannich reactions may be carried out using these systems, and in the case of the reactions using chlorotrimethylsilane and aminals the reactions can be catalytic with respect to the silane.

SYNTHESIS OF N-UNSUBSTITUTED α-ALKYLATED PYRROL-2-ACETONITRILES

Nucleophilic addition of alkyllithium compounds to in situ generated 6-dimethylamino-1-azafulvene produced the α-alkylated pyrrole Mannich bases (3).Reaction of the p-toluenesulfonic acid salt of such bases with excess sodium cyanide in wet acetonitrile, at reflux temperature, provided the corresponding α-alkylpyrrol-2-acetonitriles (5) via the putative 6-alkyl-1-azafulvenes.

1-pyrrole from Trimethyl(1-pyrrolyl)ammonium Ion

Trimethyl(1-pyrrolyl)ammonium iodide (5a) and the corresponding p-toluenesulfonate 5b are transformed by strong bases into 1-pyrrole (9), i.e. into a N-Mannich base, a type of compound novel in the pyrrole series.In this reaction, which is very fast in DMSO the cation of compounds 5 is deprotonated to form the nitrogen ylide 6.The latter undergoes a Stevens-type rearrangement to 9.Several facts, namely the negative outcome of a cross-reaction experiment with 3,4-dimethylpyrrole and of an attempt to obtain 9 from pyrrole and dimethyl(methylidene)ammonium iodide in the presence of one equivalent of sodium methoxide, as well as unsuccessful CIDNP studies point to a rearrangement mechanism via the contact ion pair 12.