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72453

Sigma-Aldrich

Tetrabutylammonium bisulfate solution

~55% in H2O

Synonym(s):

Tetrabutylammonium hydrogen sulfate solution

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N(HSO4)
CAS Number:
32503-27-8
Molecular Weight:
339.53
Beilstein:
3599663
MDL number:
MFCD00011637
UNSPSC Code:
12352107
PubChem Substance ID:
57652417
NACRES:
NA.22

form

liquid

concentration

~55% in H2O

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

Application

Tetrabutylammonium bisulfate (Bu4NHSO4) can be used as a reagent along with potassium fluoride dihydrate to synthesize β-fluoro amine derivatives by the ring-opening reaction of aziridines. It may also be utilized as a catalyst in the hydrolysis of aziridines and epoxides to corresponding β-amino alcohols and 1,2-diols, respectively.

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)

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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Ren-Hua Fan et al.
The Journal of organic chemistry, 69(2), 335-338 (2004-01-17)
Potassium fluoride combined with tetrabutylammonium bisulfate is an efficient reagent to convert a variety of aziridines derived from cyclic and acyclic alkenes to beta-fluoro amine derivatives in high yield.
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.
Kosei Sugahara et al.
Chemical communications (Cambridge, England), 48(67), 8422-8424 (2012-07-14)
A tetra-n-butylammonium (TBA) salt of a γ-Keggin -6-charged germanodecatungstate, [γ-H(2)GeW(10)O(36)](6-) (I), could act as an efficient homogeneous catalyst for Knoevenagel condensation of active methylene compounds with carbonyl compounds.
Shohei Sakashita et al.
Organic letters, 15(17), 4308-4311 (2013-08-21)
Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of tetrabutylammonium 2-pyridyltriolborate salts with various aryl (heteroaryl) chlorides can produce the corresponding desired coupling products with good to excellent yields. These tetrabutylammonium salts are more reactive than the corresponding lithium salts. The coupling reactions with
Jia Bao et al.
Environmental science and pollution research international, 21(12), 7650-7655 (2014-03-14)
Severe perfluoroalkyl acid (PFAA) contamination resulting from the fast-growing semiconductor, electrochemical, and optoelectronic industries has been determined in the river water in the vicinity of the Taipei area, Taiwan, during recent years. However, little is known about body burdens of
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