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Safety Information

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:
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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

87303-25G:
87303-INTR:
87303-5G:
87303-VAR:
87303-BULK:
87303-100G:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH1927
BCCB7401
BCBZ8871
BCBZ7302
BCBW2533

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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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