CAS 32503-27-8 Tetrabutylammonium hydrogen sulfate

Synonyms

N,N,N-tributyl-1-butanaminiusulfate(1:1)

IUPAC Name

hydrogen sulfate;tetrabutylazanium

Molecular Weight

339.53

Molecular Formula

C16H37NO4S

Canonical SMILES

CCCC[N+](CCCC)(CCCC)CCCC.OS(=O)(=O)[O-]

InChI

InChI=1S/C16H36N.H₂O4S/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-5(2,3)4/h5-16H2,1-4H3;(H2,1,2,3,4)/q+1;/p-1

InChI Key

SHFJWMWCIHQNCP-UHFFFAOYSA-M

Purity

99%

Appearance

White solid

Storage

Refrigerator

Complexity

192

Covalently-Bonded Unit Count

EC Number

251-068-5

Exact Mass

339.24433g/mol

Formal Charge

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

MeSH Entry Terms

tetra-n-butylammonium dodecylsulfate;tetra-n-butylammonium hexafluorophosphate;tetrabutylammonium;tetrabutylammonium azide;tetrabutylammonium bromide;tetrabutylammonium chloride;tetrabutylammonium cyanide;tetrabutylammonium fluoride;tetrabutylammonium hydrogen sulfate;tetrabutylammonium hydroxide;tetrabutylammonium iodide;tetrabutylammonium monophosphate;tetrabutylammonium nitrate;tetrabutylammonium perchlorate;tetrabutylammonium sulfate;tetrabutylammonium sulfate (1:1), sodium salt

Monoisotopic Mass

339.24433g/mol

Physical State

White crystal or powder

Rotatable Bond Count

Application

Tetrabutylammonium hydrogen sulfate is a versatile compound utilized for a wide range of chemical and industrial applications. As a stable, hygroscopic, white powder, its primary purpose encompasses serving as an ion-pairing reagent in liquid chromatography, facilitating the analysis of pharmaceutical compounds and metabolites. Its unique properties as a quaternary ammonium salt lend it antibacterial capabilities, attributed to the presence of a quaternary amine and counter ion. Moreover, it acts as a phase-transfer catalyst and cocatalyst in various synthesis processes, such as the hydrocarboxylation of ethylene to produce propionic acid and ketones. It plays a crucial role in N-alkylation reactions, beta-amino acid cyclization to form beta-lactams, conversion of nitriles to amides, and other key transformations in organic chemistry. Additionally, it finds application as a surface-active agent, solvent, emulsifying agent, and pigment disperser. Tetrabutylammonium hydrogen sulfate is also employed as an active ingredient in conditioners, antistatic agents, detergent sanitizers, and fabric softeners for textiles and paper products, underscoring its importance across multiple industries.

January 20, 2025

Excellent Ion-Pairing Reagent for Research

Using Alfa Chemistry's Tetrabutylammonium hydrogen sulfate in chromatography enhanced our pharmaceutical analyses significantly. Its stable, white powder form was reliable as a phase transfer catalyst. Highly recommended for efficient N-alkylation and hydrocarboxylation applications.