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374598

Sigma-Aldrich

Cetyltrimethylammonium hydrogensulfate

99%

Synonym(s):

CTAHSO4, Hexadecyltrimethylammonium hydrogen sulfate

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About This Item

Linear Formula:
CH3(CH2)15N(HSO4)(CH3)3
CAS Number:
Molecular Weight:
381.61
EC Number:
MDL number:
UNSPSC Code:
12352107
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

mp

250-260 °C (dec.) (lit.)

SMILES string

OS([O-])(=O)=O.CCCCCCCCCCCCCCCC[N+](C)(C)C

InChI

1S/C19H42N.H2O4S/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(2,3)4;1-5(2,3)4/h5-19H2,1-4H3;(H2,1,2,3,4)/q+1;/p-1

InChI key

UCRJJNVFJGKYQT-UHFFFAOYSA-M

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Application

Cetyltrimethylammonium hydrogensulfate is commonly used as a surfactant for organic transformation in the aqueous medium.
Some of the applications include:
  • Rhodium(I)-catalyzed asymmetric hydrogenation of (Z)-methyl-α-acetamidocinnamate.
  • Asymmetric palladium-catalyzed alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate.

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

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Influence of different types of amphiphiles on the rhodium (I) complex-catalyzed asymmetric hydrogenation of (Z)-methyl-α-acetamidocinnamate in aqueous medium
Grassert I, et al.
Tetrahedron, 49(30), 6605-6612 (1993)
Micellar effects upon oxidation of organic sulfides by anionic oxidants
Bacaloglu R, et al.
Journal of Physical Organic Chemistry, 5(4), 171-178 (1992)
Catalytic asymmetric alkylation in water in the presence of surfactants
Sinou D, et al.
advanced synthesis and catalysis, 345(3), 357-363 (2003)
Junqi Tang et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 103, 349-355 (2012-12-25)
Cetyltrimethyl ammonium bromide (CTAB) has been extensively applied in the solution-phase synthesis of many types of colloidal nanoparticles. However, the uses of CTAB were mainly considered as template or capping agents to form controllable shape and protect the product from
K Ranta et al.
Journal of investigational allergology & clinical immunology, 23(4), 226-233 (2013-08-24)
Immunoglobulin E-mediated allergies have doubled in prevalence during recent decades in developed countries.This increase has been attributed, in part, to high hygiene standards, which have reduced exposure to microbes. The capacity of microbes to induce type 1 helper T cell

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