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Sigma-Aldrich

Tetrahexylammonium hydrogensulfate

≥98.0% (T)

Synonym(s):

THAHS, Tetra-n-Hexylammonium Hydrogen Sulfate

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About This Item

Linear Formula:
[CH3(CH2)5]4N(HSO4)
CAS Number:
32503-34-7
Molecular Weight:
451.75
Beilstein:
4629729
EC Number:
251-069-0
MDL number:
MFCD00037675
UNSPSC Code:
12352116
PubChem Substance ID:
57653236
NACRES:
NA.22

Quality Level

100

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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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R. Bar et al.
Tetrahedron Letters, 22, 1709-1709 (1981)
Epoxidation of ?, ?-unsaturated ketones with sodium perborate.
Straub T S, et al.
Tetrahedron Letters, 36(5), 663-664 (1995)
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)
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)
N Surendran et al.
Journal of chromatography. B, Biomedical sciences and applications, 691(2), 305-312 (1997-04-11)
The objective of this research was to develop a rapid, sensitive and reliable method for the separation of phosphonodipeptide prodrugs and parent compounds to facilitate the evaluation of cell permeation using in vitro cell culture models. Separation was accomplished isocratically
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