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345857

Sigma-Aldrich

Tetrabutylammonium chloride hydrate

98%

Synonym(s):

TBAC hydrate

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N(Cl) · xH2O
CAS Number:
Molecular Weight:
277.92
Beilstein:
3765327
EC Number:
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

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Quality Level

Assay

98%

form

solid

mp

41-44 °C (lit.)

InChI

1S/C16H36N.ClH.H2O/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;;/h5-16H2,1-4H3;1H;1H2/q+1;;/p-1

InChI key

FODWRUPJCKASBN-UHFFFAOYSA-M

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Application

Tetrabutylammonium chloride (TBAC) hydrate has been used as a phase transfer catalyst in the synthesis of fullerenols[1] and in Heck-type palladium-catalyzed vinylation of organic halides in water.[2] TBAC hydrate has also been reported to be a promising candidate for cool energy storage material.[3]
Tetrabutylammonium chloride hydrate can be used:
  • As an additive in palladium-catalyzed cross-coupling reaction of heteroaromatic carboxylic acids with aryl bromides.[4]
  • To enhance the reactivity of palladium-catalyzed arylation of methyl acrylates.[5]
  • In derivatization of bis(spirodienone) calixarene having exocyclic double bonds to its chloro derivative.[6]

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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    Phase equilibrium of ionic semiclathrate hydrates formed with tetrabutylammonium bromide and tetrabutylammonium chloride.
    Sato K, et al.
    Fluid Phase Equilibria, 337, 115-118 (2013)
    On the efficiency of tetraalkylammonium salts in Heck type reactions
    Jeffery T
    Tetrahedron, 52(30), 10113-10130 (1996)
    Unexpected intermolecular Pd-catalyzed cross-coupling reaction employing heteroaromatic carboxylic acids as coupling partners
    Forgione P, et al.
    Journal of the American Chemical Society, 128(35), 11350-11351 (2006)
    Synthesis of p-tert-butylcalix-4-arene derivatives with trans-alkyl substituents on opposite methylene bridges
    Simaan S and Biali SE
    The Journal of Organic Chemistry, 68(9), 3634-3639 (2003)
    Electrical and optical properties of fullerenol Langmuir? Blodgett films deposited on polyaniline substrates.
    Rincon M E, et al.
    The Journal of Physical Chemistry B, 107(17), 4111-4117 (2003)

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