51-92-3

Usage

Uses

Used in Organic Synthesis:
Tetramethylammonium is used as a phase-transfer catalyst for facilitating the transfer of reactants between different phases in organic synthesis reactions. This enhances the efficiency and selectivity of the reactions, making it a valuable tool in the synthesis of various organic compounds.
Used in Synthesis of Other Organic Compounds:
Tetramethylammonium serves as a precursor in the synthesis of other organic compounds, contributing to the formation of a wide range of chemical products.
Used in Biochemical Research:
As a reagent, tetramethylammonium is utilized in biochemical research to study various biological processes and interactions, providing insights into the mechanisms of different biochemical systems.
Used in Energy Storage Devices:
Tetramethylammonium compounds have been explored for their potential applications in energy storage devices such as supercapacitors, owing to their high ionic conductivity. This makes them promising candidates for improving the performance of energy storage technologies.
It is crucial to handle tetramethylammonium compounds with care, as they can pose hazards if not used properly, ensuring safety in their application across various industries.

InChI:InChI=1/C4H12N/c1-5(2,3)4/h1-4H3/q+1

Upstream product

• 129916-53-6 C₄H₁₂N⁽¹⁺⁾*CH₅N 
• 151168-20-6 C₆H₆*C₄H₁₂N⁽¹⁺⁾ 
• 3878-60-2 C₇H₈*C₄H₁₂N⁽¹⁺⁾ 
• 24400-15-5 dimethylchloronium 
• 75-50-3 trimethylamine 
• 24400-21-3 ethyl-methyl-chloronium 
• 67-56-1 methanol 
• 56-84-8 L-Aspartic acid 
• 77-78-1 dimethyl sulfate 
• 62483-45-8 tetramethylammonium chloroperchloratoaluminate 

Downstream Products

• 112-62-9 Methyl oleate 
• 96-96-8 4-methoxy-2-nitroaniline 
• 75-50-3 trimethylamine 
• 25493-69-0 (4aS,6aS,6bR,10S,12aR)-methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate 
• 593-79-3 dimethylselenide 
• 25255-90-7 tetramethylammonium benzoate 
• 107-46-0 Hexamethyldisiloxane 
• 107-51-7 octamethyltrisiloxabe 
• 141-62-8 decamethyltetrasiloxane 
• 556-67-2 octamethylcyclotetrasiloxane 
• 7726-95-6 bromine 
• 62-75-9 N-Nitrosodimethylamine 
• 12386-10-6 tetramethylammonium octahydrotriborate 
• 12557-40-3 {(CH₃)4N}⁽¹⁺⁾*{(B₁₀H₁₀PC₆H₅)Mn(CO)3}^(1-)={(CH₃)4N}{(B₁₀H₁₀PC₆H₅)Mn(CO)3} 

Relevant academic research and scientific papers

13C and 15N solid-state MAS NMR study of the conversion of methanol and ammonia over H-RHO and H-SAPO-34 microporous catalysts

13C and 15N MAS NMR have been used to study the conversion of methanol and ammonia over H-SAPO-34 and H-RHO using sealed glass ampoules as microreactors under static batch conditions. The product peaks were well resolved in the 13C NMR spectra whereas the 15N NMR spectra gave only a single broad peak making it impossible to follow the reaction by observing this nucleus. Both catalysts give the tetramethyammonium cation whereas only zeolite H-RHO produces the monomethylammonium cation.

Unconventional Ionic Hydrogen Bonds. 1. Complexes of Quaternary Ions with n- and ?-Donors

interaction energies are obtained from the clustering of quaternary onium ions with n-donor solvent molecules.The dissociation energies (ΔHoD) of Me4N(1+) clustered with the n-donor H2O, MeOH, MeNH2, and Me3N and with the ?-donors benzene and toluene range between 8 and 10 kcal mol-1.With the weak, bulky n-donor MeCl the interaction is weaker (6.5 kcal mol-1) while the more polar ligands Me2CO and MeCONMe2 attach strongly (14.6 and 18.0 kcal mol-1, respectively) to Me4N(1+).Strong interactions, 20-23 kcal mol-1, are also observed with polyethers and CH3CO-gly-OCH3, indicating polydentate complexing.The attachment energies of ligands to Et4N(1+) are smaller by 2 kcal mol-1 than those to Me4N(1+).Ab initio calculations show that in the Me4N(1+)*H2O, MeOH, MeNH2, and MeCl complexes the ligands attach electrostatically to a cavity created by protons of three CH3 gropus rather than hydrogen bonding to one proton or to one CH3 group.Both experiment and theory indicate that a second solvent molecule (H2O or CH3OH) attaches preferentially to the first solvent molecule rather than to Me4N(1+).

Chloronium Ions as Alkylating Agents in the Gas-Phase Ion-Molecule Reactions with Negative Temperature Dependence

The kinetics of the reactions Me2Cl+ + B = MeB+ + MeCl and MeEtCl+ + B = MeB+ or (EtB+) + EtCl (or MeCl) were studied with a pulsed-electron-beam, high-pressure mass spectrometer.At room temperature the rate constants were found to increase in the order B = benzene, toluene, isopropylbenzene, EtOH, Me2O, Et2O.At this point k become equal to the orbiting capture rate constant k1 ca. 10-9 molecule-1 cm3 s-.NH3 and Me3N were alkylated at orbiting capture rates.The temperature dependence of the rate constants for B = toluene, Me2O, and Et2O was examined.The rate constants were found to increase with decrease of temperature.This increase continued until the rate constants reached the magnitude of the orbiting rate constant kL.The rates remained approximately independent of temperature below this temperature.At low temperatures the collision-stabilized Me2Cl+B and MeEtCl+B could be observed.The temperature dependence of the equilibrium Me2Cl+ + toluene = (Me2Cl-toluene)+ was measured and led to the corresponding ΔHo and ΔSo.The reaction Me2Cl+ + benzene = Me-benzene+ + MeCl was found to have positive temperature dependence.On the basis of the above data it is suggested that the reactions Me2Cl+ + B = MeB+ + MeCl have an internal barrier in the potential energy of the reaction coordinate.This barrier protrudes above the energy level of the reactants (Me2Cl+ + B) for B = benzene.This leads to positive temperature dependence.For all other B, the top of the internal barrier lies below the level of the reactants and sinks lower, roughly in the order of increasing basicity of B.This lead to negative temperature dependence (toluene, isopropylbenzene, Me2O, Et2O).For B = NH3, MeNH2, Me3N, the barrier is so low that the reactions have orbiting capture rates equal to kL.Alkylation of bases B by chloronium ions like Me2Cl+ might have considerable utility in mass spectrometric analysis by chemical ionization.Ethers can be distinguished from alcohols and tertiary amines from primary and secondary amines.The alkylated ethers and the tertiary amines have no protic hydrogens and therefore do not form strongly hydrogen-bonded adducts.