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Sigma-Aldrich

Tetrabutylammonium p-toluenesulfonate

99%

Synonym(s):

p-Toluenesulfonic acid tetrabutylammonium salt

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N(CH3C6H4SO3)
CAS Number:
7182-86-7
Molecular Weight:
413.66
Beilstein:
3643278
EC Number:
230-548-8
MDL number:
MFCD00043227
UNSPSC Code:
12352116
PubChem Substance ID:
24861983
NACRES:
NA.22

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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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