1821-38-1

Basic information

• Product Name: N-ethyl-2-methyl-aniline
• Synonyms: Pyrrolidine,2-ethylidene-1-methyl;N-Methyl-2-ethylidenepyrrolidine;2-Methylamino-1-aethyl-benzol;N-methyl-o-ethylaniline;2-Aethyl-N-methyl-anilin;2-ethyl-N-methyl-aniline;N-Methyl-2-aethyl-anilin;N-methyl ortho-ethylaniline;N-methyl-2-ethylphenylamine;1-methyl-2-ethylidenepyrrolidine
• CAS NO: 1821-38-1
• Molecular Formula: C₉H₁₃N
• Molecular Weight: 135.209
• Mol File: 1821-38-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 218°Cat760mmHg
• Flash Point: 88.9°C
• Density: 0.954g/cm³
• CAS DataBase Reference: N-ethyl-2-methyl-aniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-ethyl-2-methyl-aniline(1821-38-1)
• EPA Substance Registry System: N-ethyl-2-methyl-aniline(1821-38-1)

Safety Data

• Hazardous Substances Data: 1821-38-1(Hazardous Substances Data)

Upstream product

• 2860-30-2 N-(2-ethylphenyl)formamide 
• 611-21-2 N,2-dimethylaniline 
• 74-88-4 methyl iodide 
• 95-53-4 o-toluidine 
• 67-56-1 methanol 
• 578-54-1 ortho-ethylaniline 
• 62001-35-8 N-(1-benzotriazolylmethyl)-2-methylaniline 
• 551-93-9 2-aminoacetophenone 
• 1859-75-2 o-(methylamino)acetophenone 
• 932-32-1 N-methyl-2-chloroaniline 
• 160852-85-7 2-[2-(2-methoxyethoxy)ethoxy]ethyl methyl carbonate 
• 13519-87-4 N-allyl-N-methyl-o-chloroaniline 
• 97-93-8 triethylaluminum 
• 128113-82-6 (1S,1'S)-N-(1'-phenylethyl)-1-<2''-(methylamino)phenyl>ethylamine 

Downstream Products

• 79018-57-8 Pd(CH₃NHC₆H₄CH₂CH₃)2Cl₂ 
• 578-54-1 ortho-ethylaniline 
• 125681-81-4 α-methyl-2-(methylamino)benzenemethanol 
• 3558-28-9 1,3-dimethyl-2-phenyl-1H-indole 
• 857622-44-7 acetic acid-(2-ethyl-N-methyl-anilide) 

Relevant articles and documents

Ruthenium(ii) complexes with N-heterocyclic carbene-phosphine ligands for theN-alkylation of amines with alcohols

Metal hydride complexes are key intermediates forN-alkylation of amines with alcohols by the borrowing hydrogen/hydrogen autotransfer (BH/HA) strategy. Reactivity tuning of metal hydride complexes could adjust the dehydrogenation of alcohols and the hydrogenation of imines. Herein we report ruthenium(ii) complexes with hetero-bidentate N-heterocyclic carbene (NHC)-phosphine ligands, which realize smart pathway selection in theN-alkylated reactionviareactivity tuning of [Ru-H] species by hetero-bidentate ligands. In particular, complex6cbwith a phenyl wingtip group and BArF?counter anion, is shown to be one of the most efficient pre-catalysts for this transformation (temperature is as low as 70 °C, neat conditions and catalyst loading is as low as 0.25 mol%). A large variety of (hetero)aromatic amines and primary alcohols were efficiently converted into mono-N-alkylated amines in good to excellent isolated yields. Notably, aliphatic amines, challenging methanol and diamines could also be transformed into the desired products. Detailed control experiments and density functional theory (DFT) calculations provide insights to understand the mechanism and the smart pathway selectionvia[Ru-H] species in this process.

Improved and General Manganese-Catalyzed N-Methylation of Aromatic Amines Using Methanol

A novel lutidine-based manganese PNP-pincer complex has been synthesized for the selective N-methylation of aromatic amines with methanol. Using borrowing hydrogen methodology, a selection of differently functionalized aniline derivatives is selectively methylated in good yields.

Selective N,N-dimethylation of primary aromatic amines with methyl alkyl carbonates in the presence of phosphonium salts

In the presence of onium salts, at 140-170 °C. methyl alkyl carbonates [1a-c, ROCO2Me, R = MeO(CH2)2[O(CH 2)2]n; n = 2-0, respectively] react with primary aromatic amines (XC6H4NH2, X = p-OMe, p-Me, H, p-Cl, p-CO2Me, o-Et, and 2,3-Me2C 6H3NH2) to yield the corresponding N,N-dimethyl derivatives (ArNMe2) with high selectivity (up to 96%) and good isolated yields (78-95%). Phosphonium salts (e.g., Ph3PEtI and n-Bu4PBr) are particularly efficient catalysts. Overall, a solvent-free reaction is coupled with safe methylating agents (1a-c) made from nontoxic dimethyl carbonate.