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86868

Sigma-Aldrich

Tetrabutylammonium bisulfate

puriss., ≥99.0% (T)

Synonym(s):

Tetrabutylammonium hydrogen sulfate

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N(HSO4)
CAS Number:
32503-27-8
Molecular Weight:
339.53
Beilstein:
3599663
EC Number:
251-068-5
MDL number:
MFCD00011637
UNSPSC Code:
12352100
PubChem Substance ID:
57653204
NACRES:
NA.21

grade

puriss.

Quality Level

200

Assay

≥99.0% (T)

form

crystals

mp

169-173 °C

solubility

H2O: soluble 10 % (w/v), clear, colorless

functional group

amine

SMILES string

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

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

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General description

Tetrabutylammonium bisulfate, a quaternary ammonium salt, is a phase-transfer reagent.

Application

Tetrabutylammonium bisulfate may be employed in the following studies:
  • As a catalyst during the synthesis of β-amino alcohols and 1,2-diols.
  • As a phase transfer catalyst for the synthesis of asymmetrical ethers.
  • To compose the mobile phase for use in high performance liquid chromatographic (HPLC) analysis.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314,H412

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 2

Flash Point(F)

348.1 °F - closed cup

Flash Point(C)

175.6 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF3084V
BCCM2154
BCCM2600
WXBF4453V
WXBF1166V

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Phase-transfer synthesis of monoalkyl ethers of oligoethylene glycols.
Gibson T.
The Journal of Organic Chemistry, 45(6), 1095-1098 (1980)
Polyesters bearing furan moieties: IV. Solution and interfacial polycondensation of 2, 2'-bis (5-chloroformyl-2-furyl) propane with various diols and bisphenols.
Gharbi S, et al.
European Polymer Journal, 36(3), 463-472 (2000)
Ren-Hua Fan et al.
Organic & biomolecular chemistry, 1(9), 1565-1567 (2003-08-21)
Bu4NHSO4 (TBAHS) is an effective catalyst for the hydrolysis of aziridines and epoxides under mild and non-metal conditions to give the corresponding beta-amino alcohols and 1,2-diols in high yields. The catalyst can be recycled.
Erythrocytic adenosine monophosphate as an alternative purine source in Plasmodium falciparum.
Cassera MB, et al.
The Journal of Biological Chemistry, 283(47), 32889-32899 (2008)
David J Posson et al.
Nature structural & molecular biology, 20(2), 159-166 (2012-12-25)
Understanding how ion channels open and close their pores is crucial for comprehending their physiological roles. We used intracellular quaternary ammonium blockers, electrophysiology and X-ray crystallography to locate the voltage-dependent gate in MthK potassium channels from Methanobacterium thermoautotrophicum. Blockers bind
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