18265-23-1

Basic information

• Product Name: N,N,N-tribenzyl methylammonium iodide
• Synonyms: N,N,N-tribenzyl methylammonium iodide
• CAS NO: 18265-23-1
• Molecular Weight: 429.344
• Mol File: 18265-23-1.mol

Chemical Properties

• CAS DataBase Reference: N,N,N-tribenzyl methylammonium iodide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,N-tribenzyl methylammonium iodide(18265-23-1)
• EPA Substance Registry System: N,N,N-tribenzyl methylammonium iodide(18265-23-1)

Safety Data

• Hazardous Substances Data: 18265-23-1(Hazardous Substances Data)

Upstream product

• 620-40-6 tribenzylamine 
• 74-88-4 methyl iodide 

Downstream Products

• 102-05-6 N-methyldibenzylamine 
• 767-90-8 (2-ethylphenyl)methanol 

Relevant articles and documents

Tribenzyl(methyl)ammonium: A Versatile Counterion for the Crystallization of Nanojars with Incarcerated Selenite and Phosphite Ions and Tethered Pyrazole Ligands

One hundred and thirty-five years after its initial discovery, the crystal structure of the tribenzyl(methyl)ammonium (TBMA+) cation is reported for the first time (as the nitrate salt). It is shown that TBMA+ is an excellent counterion for the crystallization of large supramolecular assemblies. Thus, single crystals of previously uncrystallizable nanojars with incarcerated selenite and phosphite ions, as well as tethered pyrazole ligands, have been successfully grown by solvent vapor diffusion into solutions with added (TBMA)NO3. X-ray diffraction studies reveal a variety of possible noncovalent interactions between pairs of TBMA+ cations. Indeed, the structurally adaptable TBMA+ dimer can take on different shapes and sizes to maximize supramolecular interactions with neighboring molecules and to fill up voids in the crystal lattice. The new nanojar crystal structures (TBMA)(Bu4N)[SeO3?{Cu(OH)(pz)}28] and (TBMA)2[HPO3?{Cu(OH)(pz)}29] (pz = pyrazolate) provide unprecedented examples of noncovalently bound selenite and phosphite ions in supramolecular complexes. The use of TBMA+ counterions has also allowed for the crystallization of a nanojar based on tethered pyrazole ligands, (TBMA)2[SO4?{Cu28(OH)28(pzCH2CH2pz)14}]. The synthesis and mass spectrometric studies of the new nanojars are presented along with crystallographic studies detailing the nanojar structure, anion binding, and nanojar-counterion/counterion-counterion supramolecular interactions in the crystal lattice. Finally, the binding of SeO32- and SO42- ions by the same Cu28 nanojar and the binding of HPO32-, CO32-, and SO42- ions by the same Cu29 nanojar are contrasted, and the δ/λ chelate-ring isomerism in the tethered-ligand nanojar is discussed.

Ni-Catalyzed Iterative Alkyl Transfer from Nitrogen Enabled by the in Situ Methylation of Tertiary Amines

Current methods to achieve transition-metal-catalyzed alkyl carbon-nitrogen (C-N) bond cleavage require the preformation of ammonium, pyridinium, or sulfonamide derivatives from the corresponding alkyl amines. These activated substrates permit C-N bond cleavage, and their resultant intermediates can be intercepted to affect carbon-carbon bond-forming transforms. Here, we report the combination of in situ amine methylation and Ni-catalyzed benzalkyl C-N bond cleavage under reductive conditions. This method permits iterative alkyl group transfer from tertiary amines and demonstrates a deaminative strategy for the construction of Csp3-Csp3 bonds. We demonstrate PO(OMe)3 (trimethylphosphate) to be a Ni-compatible methylation reagent for the in situ conversion of trialkyl amines into tetraalkylammonium salts. Single, double, and triple benzalkyl group transfers can all be achieved from the appropriately substituted tertiary amines. Transformations developed herein proceed via recurring events: The in situ methylation of tertiary amines by PO(OMe)3, Ni-catalyzed C-N bond cleavage, and concurrent Csp3-Csp3 bond formation.