3983-91-3

Basic information

• Product Name: TETRAMETHYLAMMONIUM P-TOLUENESULFONATE
• Synonyms: TETRAMETHYLAMMONIUM P-TOLUENESULFONATE;Tetramethylammoniumtoluenesulfonate;tetramethylammonium toluene-p-sulphonate;Tetramethylaminium·tosylate;TetraMethylaMMoniuM tosylate;N1,1,1,1TS;Tetramethylammonium p-Toluenesulfonate;[N1,1,1,1] TsO
• CAS NO: 3983-91-3
• Molecular Formula: C₄H₁₂N*C₇H₇O₃S
• Molecular Weight: 245.34
• EINECS: 223-625-2
• Product Categories: Ammonium Polyhalides, etc. (Quaternary);Quaternary Ammonium Compounds
• Mol File: 3983-91-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Water Solubility: almost transparency in Water
• CAS DataBase Reference: TETRAMETHYLAMMONIUM P-TOLUENESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAMETHYLAMMONIUM P-TOLUENESULFONATE(3983-91-3)
• EPA Substance Registry System: TETRAMETHYLAMMONIUM P-TOLUENESULFONATE(3983-91-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 3983-91-3(Hazardous Substances Data)

Usage

General Description

Tetramethylammonium p-toluenesulfonate is a quaternary ammonium salt with the chemical formula C9H18NO3S. It is a white crystalline powder that is soluble in water and organic solvents. This chemical serves as a phase transfer catalyst and is commonly used in organic synthesis as a reagent for the conversion of alcohols to alkyl chlorides. It is also utilized as an electrolyte in semiconductor industries and as a stabilizer in the synthesis of nanoparticles. Tetramethylammonium p-toluenesulfonate is considered to be a low hazard chemical, with a low potential for skin irritation and no significant environmental toxicity reported.

Upstream product

• 75-58-1 tertamethylammonium iodide 
• 104-15-4 toluene-4-sulfonic acid 
• 64-20-0 tetramethylammonium bromide 
• 75-59-2 tetramethyl ammoniumhydroxide 

Downstream Products

• 645388-99-4 bis(2,9-dimethyl-1,10-phenanthroline)copper(I) tosylate 

Relevant articles and documents

C(sp3)-O bond-forming reductive elimination from PdIV with diverse oxygen nucleophiles

This article describes an investigation of C(sp3)-O bond-forming reductive elimination reactions from PdIV complexes. Phenoxide, acetate, difluoroacetate, dimethylphosphate, tosylate, and nitrate nucleophiles are shown to participate in this reaction. In all cases, C(sp3)-O bond formation occurs with high selectivity over potentially competing C(sp2)-O coupling. Additives have a profound impact on the chemoselectivity of these reductive elimination reactions. An excess of RO- was found to limit competing C(sp3)-C(sp2) bond-forming reductive elimination, while the presence of Lewis acidic cations was found to suppress competing C(sp3)-F coupling. Mechanistic investigations were conducted, and the available data are consistent with a sequence involving pre-equilibrium dissociation of the oxyanion ligand (RO-) followed by nucleophilic attack of RO- on a cationic PdIV-alkyl intermediate.

Backscattering Interferometry: An alternative approach for the study of hydrogen bonding interactions in organic solvents

Intermolecular interactions involving hydrogen bonds are responsible for catalysis and recognition. Traditional methods used to study hydrogen-bonding interactions are generally limited to relatively large volumes and high substrate concentrations. Backscattering Interferometry (BSI) provides a microfluidic platform to study these interactions in nonaqueous media at micromolar to nanomolar concentrations in picoliter volumes by monitoring changes in the refractive index.

Constituent Analysis of the Interaction of Solvents with the Leaving Group Anions for SN1-E1 Reactions. Thermodynamic Evidence for the Nature of the Conjugate Base of p-Nitrophenylhydrazonomalononitrile

Enthalpies of solution in dimethyl sulphoxide and in methanol for the tetraethylammonium salt of the conjugate base of p-nitrophenylhydrazonomalononitrile were measured and compared with those of tetraethylammonium chloride.The former salt is more stable in the strongly dipolar aprotic solvent dimethyl sulphoxide than in the protic solvent methanol, whereas the latter is more stable in methanol because of hydrogen bonding of the solvent with chloride ion.Single ion enthalpies of transfer were determined in acetonitrile-methanol mixtures for the hydrazono anion as well as for tosylate ion and were dissected into constituent terms; a 'more physical' and a 'specific' interaction, solvation being due to hydrogen bonding.The hydrazono anion resembles BBun4- and ClO4- in that the contribution from the latter term is negligible.On the other hand, tosylate ion is susceptible to hydrogen bonding as is halide ion.The result is consistent with the kinetic behaviour of the leaving group anions for SN1-E1 reactions.