87303

Sigma-Aldrich

Tetrahexylammonium hydrogensulfate

≥98.0% (T)

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

Quality Level

assay

≥98.0% (T)

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.

Packaging

5, 25 g in glass bottle

Other Notes

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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Epoxidation of ?, ?-unsaturated ketones with sodium perborate.
Straub T S, et al.
Tetrahedron Letters, 36(5), 663-664 (1995)
R. Bar et al.
Tetrahedron Letters, 22, 1709-1709 (1981)
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)
Zeynep S Teksin et al.
Journal of controlled release : official journal of the Controlled Release Society, 116(1), 50-57 (2006-10-20)
Parallel Artificial Membrane Permeability Assay (PAMPA) is a method to screen drug candidates for membrane permeability. The objective was to characterize the transport of a model weak base, metoprolol, across a three lipid-component PAMPA system (denoted A-PAMPA, for anionic-PAMPA) and...
The effects of tetrahexylammonium chloride on calcium mobilization from cerebellar microsomes.
L G Sayers et al.
Biochemical Society transactions, 21(2), 105S-105S (1993-05-01)

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