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335991

Sigma-Aldrich

Tetrabutylammonium acetate

97%

Linear Formula:
(CH3CH2CH2CH2)4N(OCOCH3)
CAS Number:
Molecular Weight:
301.51
Beilstein:
3599376
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

mp

95-98 °C (lit.)

SMILES string

CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC

InChI

1S/C16H36N.C2H4O2/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-2(3)4/h5-16H2,1-4H3;1H3,(H,3,4)/q+1;/p-1

InChI key

MCZDHTKJGDCTAE-UHFFFAOYSA-M

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General description

Tetrabutylammonium acetate (TBAA) is a phase transfer catalyst (PTC).

Application

Tetrabutylammonium acetate can be used:
  • To catalyze the alkynylation of carbonyl compounds with trimethylsilylacetylenes providing good yields of propargylic alcohols.
  • Along with tetrabutylammonium bromide (TBAB) as a molten reaction medium in the synthesis of 4-aryl-2-quinolones.
  • As a promoter in the regioselective direct arylation of azoles (1-methylpyrazole, oxazole, and thiazole) with aryl bromides in presence of palladium acetate catalyst.
  • As an ionic liquid to dissolve cellulose in the presence of DMSO co-solvent.
  • As an activator in the synthesis of disubstituted alkynes through copper-free Sonogashira coupling reaction.

Packaging

5, 10, 50 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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

Certificate of Analysis

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Certificate of Origin

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