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358681

Sigma-Aldrich

Tetrabutylammonium p-toluenesulfonate

99%

Synonym(s):
p-Toluenesulfonic acid tetrabutylammonium salt
Linear Formula:
(CH3CH2CH2CH2)4N(CH3C6H4SO3)
CAS Number:
Molecular Weight:
413.66
Beilstein:
3643278
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

mp

70-72 °C (lit.)

SMILES string

Cc1ccc(cc1)S([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC

InChI

1S/C16H36N.C7H8O3S/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-6-2-4-7(5-3-6)11(8,9)10/h5-16H2,1-4H3;2-5H,1H3,(H,8,9,10)/q+1;/p-1

InChI key

REAVCZWUMGIGSW-UHFFFAOYSA-M

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Application

Tetrabutylammonium p-toluenesulfonate (TBAOTs) can be used as:
  • A phase transfer catalyst (PTC) in SN2 fluorinations.
  • An electrolyte in the preparation of conducting polymer polypyrrole (PPy) by electrochemical polymerization technique.
  • A reagent to synthesize 1-alkynyl sulfonates from 1-alkynyl-bromanes by Michael-carbene rearrangement reaction.

Packaging

2, 10 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Actuator based on doping/undoping-induced volume change in anisotropic polypyrrole film
Okamoto T, et al.
Thin Solid Films, 393(1-2), 383-387 (2001)
Synthesis, Structure, and Reaction of 1-Alkynyl (aryl)-λ-bromanes
Ochiai M, et al.
Journal of the American Chemical Society, 125(50), 15304-15305 (2003)
Tetrabutylammonium tosylate as inert phase-transfer catalyst: The key to high efficiency SN2 radiofluorinations
Orlovskaya V, et al.
Applied Radiation and Isotopes, 109195-109195 (2020)
Michelle L Ingalsbe et al.
Bioorganic & medicinal chemistry letters, 19(17), 4984-4987 (2009-08-08)
Due to the increasing number of strains of drug-resistant bacteria, the development of new antibiotics has become increasingly important. The antibacterial properties of quaternary amines and their derivatives on both Gram-positive and Gram-negative bacteria are well known. However, an encompassing...

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