37125-92-1

Basic information

• Product Name: 2-METHYL-3-N,N-DIMETHYLAMINOMETHYLINDOLE
• Synonyms: 3-(DIMETHYLAMINOMETHYL)-2-METHYLINDOLE;2-METHYL-3-N,N-DIMETHYLAMINOMETHYLINDOLE;2-METHYLGRAMINE;DIMETHYL-(2-METHYL-1H-INDOL-3-YLMETHYL)-AMINE;1H-Indole-3-methanamine, N,N,2-trimethyl-;N,N-dimethyl-1-(2-methyl-1H-indol-3-yl)methanamine
• CAS NO: 37125-92-1
• Molecular Formula: C₁₂H₁₆N₂
• Molecular Weight: 188.27
• Mol File: 37125-92-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 120-121 °C(Solv: acetone (67-64-1); ethanol (64-17-5))
• Boiling Point: 309.6 °C at 760 mmHg
• Flash Point: 141.1 °C
• Appearance: /
• Density: 1.077 g/cm³
• Vapor Pressure: 0.000631mmHg at 25°C
• Refractive Index: 1.618
• PKA: 17.57±0.30(Predicted)
• CAS DataBase Reference: 2-METHYL-3-N,N-DIMETHYLAMINOMETHYLINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-3-N,N-DIMETHYLAMINOMETHYLINDOLE(37125-92-1)
• EPA Substance Registry System: 2-METHYL-3-N,N-DIMETHYLAMINOMETHYLINDOLE(37125-92-1)

Safety Data

• Hazardous Substances Data: 37125-92-1(Hazardous Substances Data)

Usage

General Description

2-Methyl-3,N,N-dimethylaminomethylindole is a chemical compound belonging to the indole family, which is often found in many crucial biological molecules. This specific compound has a molecular formula of C12H16N2 and features a methyl group bonded to the 2-position of the indole ring, as well as a dimethylaminomethyl group at the 3-position. Despite the detailed understanding of its structure, the exact properties, applications, and safety profile of 2-Methyl-3,N,N-dimethylaminomethylindole are not commonly documented, which suggests that it might be a relatively obscure or less-studied compound within the domain of organic chemistry. Therefore, personal protective equipment should be used and caution exercised when handling this compound, especially without specific information on its hazard and toxicity levels.

InChI:InChI=1/C12H16N2/c1-9-11(8-14(2)3)10-6-4-5-7-12(10)13-9/h4-7,13H,8H2,1-3H3

Upstream product

• 95-20-5 2-methyl-1H-indole 
• 50-00-0 formaldehyd 
• 124-40-3 dimethyl amine 
• 33797-51-2 eschenmoser's salt 
• 506-59-2 N,N-dimethylammonium chloride 

Downstream Products

• 1912-43-2 2-methyl-3-indoleacetic acid 
• 4071-16-3 2-(2-methyl-1H-indol-3-yl)acetonitrile 
• 82255-15-0 3-<2-(N-benzyloxycarbonyl-L-prolylamido)-2,2-diethoxycarbonylethyl>-2-methylindole 
• 36634-78-3 (E)-2-methyl-3-styryl-1H-indole 
• 72742-77-9 1-[[1,1-dimethyl-2-(2-methyl-3-indolyl)ethyl]amino]-3-(2-methylphenoxy)-2-propanol 
• 72742-82-6 2-[2-hydroxy-3-[[2-(2-methyl-1H-indol-3-yl)-1,1-dimethylethyl]amino]propoxy]benzonitrile 
• 75057-62-4 2-amino-4,5-dibromobenzoic acid 
• 20776-50-5 2-amino-4-bromobenzoic acid 
• 82255-19-4 3-<2-(2'-acetamidophenyl-2-oxoethyl)>-pyrrolo-<1,2,a>-pyrazine-1,4-dione 
• 82255-16-1 3-<2-(N-benzyloxycarbonyl-L-prolylamido)-2-carboxyethyl>-2-methylindole 
• 82255-17-2 3-<2-(N-benzyloxycarbonyl-L-prolylamido)-2-ethoxycarbonylethyl>-2-methylindole 
• 83020-27-3 1,3-Dioxo-2-phenyl-2,3,3a,4,10,10a-hexahydro-1H-pyrrolo[3,4-b]carbazole-5-carboxylic acid tert-butyl ester 
• 21495-41-0 2-amino-3-(2-methyl-1H-indol-3-yl)propanoic acid 
• 1609030-75-2 (E)-N-(2-(3-((dimethylamino)methyl)-2-methyl-1H-indol-1-yl)ethyl)-3-(3,4,5-trimethoxyphenyl)acrylamide 

Relevant articles and documents

A convenient metal-free reagent for the generation and capture of trifluoromethanethiol

O-Octadecyl-S-trifluorothiolcarbonate is a cheap and storable crystalline source of trifluoromethanethiol that can be prepared in two steps on a multigram scale from trifluoroacetic anhydride and sodium O-octadecyl-dithiocarbonate (xanthate). It reacts directly with gramines or with α-bromoketones and -esters in the presence of KF and pyrrolidine to give the corresponding trifluoromethyl sulfides in generally high yield.

Catalyst-Controlled Regiodivergence in Rearrangements of Indole-Based Onium Ylides

We have developed catalyst-controlled regiodivergent rearrangements of onium-ylides derived from indole substrates. Oxonium ylides formed in situ from substituted indoles selectively undergo [2,3]- and [1,2]-rearrangements in the presence of a rhodium and a copper catalyst, respectively. The combined experimental and density functional theory (DFT) computational studies indicate divergent mechanistic pathways involving a metal-free ylide in the rhodium catalyzed reaction favoring [2,3]-rearrangement, and a metal-coordinated ion-pair in the copper catalyzed [1,2]-rearrangement that recombines in the solvent-cage. The application of our methodology was demonstrated in the first total synthesis of the indole alkaloid (±)-sorazolon B, which enabled the stereochemical reassignment of the natural product. Further functional group transformations of the rearrangement products to generate valuable synthetic intermediates were also demonstrated.

I2-induced cascade cyclization and dearomatization of indoles for the highly efficient synthesis of iodinated and vinylic spiroindolenines

The spiroindolenine framework is a privileged heterocyclic motif and is widely present in numerous indole alkaloids. Herein, we develop a metal-free and environmentally friendly approach for the intramolecular cascade cyclization and dearomatization of indole derivatives to selectively afford iodinated and vinylic spiroindolenines by a substrate-controlled strategy. Simple operation, mild conditions, and high yield make this strategy a green and attractive pathway to construct functionalizable spiroindolenine scaffolds, which could be converted into diverse useful spiroindolenine derivatives.