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87303

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/REAXYS Number:
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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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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)
R. Bar et al.
Tetrahedron Letters, 22, 1709-1709 (1981)
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)
Masamichi Yamanaka et al.
Journal of the American Chemical Society, 126(9), 2939-2943 (2004-03-05)
Resorcinarene 1b forms a hexameric assembly in water-saturated CDCl(3) that encapsulates one tetraalkylammonium salt (2(+)Br(-)). The remaining space is occupied by coencapsulated solvent molecules. A maximum of three and minimum of one CHCl(3) molecule were found inside of capsules with
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