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Sigma-Aldrich

Tetrahexylammonium hydrogensulfate

≥98.0% (T)

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Synonym(s):
THAHS, Tetra-n-Hexylammonium Hydrogen Sulfate
Linear Formula:
[CH3(CH2)5]4N(HSO4)
CAS Number:
Molecular Weight:
451.75
Beilstein:
4629729
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥98.0% (T)

form

crystals

mp

98-100 °C (lit.)

SMILES string

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

InChI

1S/C24H52N.H2O4S/c1-5-9-13-17-21-25(22-18-14-10-6-2,23-19-15-11-7-3)24-20-16-12-8-4;1-5(2,3)4/h5-24H2,1-4H3;(H2,1,2,3,4)/q+1;/p-1

InChI key

RULHPTADXJPDSN-UHFFFAOYSA-M

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Application

Tetrahexylammonium hydrogensulfate can be used as a phase-transfer agent to facilitate certain organic reactions in a two-liquid phase system. For example:
  • Epoxidation of α,β-unsaturated ketones in a biphasic dichloromethane/water mixture using sodium perborate.
  • Transfer hydrogenolysis of aryl bromides by aqueous sodium formate catalyzed by palladium-triphenylphospine.
  • Carbonylation of benzylic and allylic bromides to synthesize carboxylic esters.

Other Notes

Lipophilic phase transfer catalyst. Most efficient catalyst in ruthenium-catalyzed reactions

Pictograms

Exclamation mark

Signal Word

Warning

Hazard 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

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R. Bar et al.
Tetrahedron Letters, 22, 1709-1709 (1981)
Catalytic carbonylation of benzylic and allylic bromides by a rhodium zwitterionic complex under phase transfer catalysis conditions
Amaratunga S and Alper H
Journal of Organometallic Chemistry, 488, 25-28 (1995)
Epoxidation of ?, ?-unsaturated ketones with sodium perborate.
Straub T S, et al.
Tetrahedron Letters, 36(5), 663-664 (1995)
Transfer hydrogenolysis of aryl bromides by sodium formate and palladium?phosphine catalyst under phase transfer conditions.
Bar R, et al.
J. Mol. Catal., 16(2), 175-180 (1982)
Y C Ho et al.
Digestive diseases and sciences, 33(4), 435-442 (1988-04-01)
Our purpose is to develop a standard method for preparing the bile for beta-glucuronidase determination by removal of bile acids and conjugated bilirubin which interfere with its activity. The bile acids and conjugated bilirubin in their purified solutions and in

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