87303
Tetrahexylammonium hydrogensulfate
≥98.0% (T), crystals
Synonym(s):
THAHS, Tetra-n-Hexylammonium Hydrogen Sulfate
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About This Item
Linear Formula:
[CH3(CH2)5]4N(HSO4)
CAS Number:
Molecular Weight:
451.75
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352116
EC Number:
251-069-0
MDL number:
Beilstein/REAXYS Number:
4629729
Product Name
Tetrahexylammonium hydrogensulfate, ≥98.0% (T)
Quality Level
assay
≥98.0% (T)
form
crystals
reaction suitability
core: ammonium
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
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
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signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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)
Epoxidation of ?, ?-unsaturated ketones with sodium perborate.
Straub T S, et al.
Tetrahedron Letters, 36(5), 663-664 (1995)