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Merck
CN

335991

Tetrabutylammonium acetate

97%

Synonym(s):

N,N,N-tributyl-1-butanaminium acetate, Tetra-n-butylammonium acetate

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N(OCOCH3)
CAS Number:
Molecular Weight:
301.51
UNSPSC Code:
12352116
NACRES:
NA.22
PubChem Substance ID:
EC Number:
234-101-8
Beilstein/REAXYS Number:
3599376
MDL number:
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Product Name

Tetrabutylammonium acetate, 97%

InChI key

MCZDHTKJGDCTAE-UHFFFAOYSA-M

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

SMILES string

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

assay

97%

mp

95-98 °C (lit.)

Quality Level

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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.

General description

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

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Chemistry Letters (Jpn), 35, 1002-1002 (2006)
Mild Palladium?Catalyzed Regioselective Direct Arylation of Azoles Promoted by Tetrabutylammonium Acetate
Bellina F, et al.
European Journal of Organic Chemistry, 25(349), 5621-5630 (2013)
4?Aryl?2?quinolones through a Pseudo?Domino Heck/Buchwald?Hartwig Reaction in a Molten Tetrabutylammonium Acetate/Tetrabutylammonium Bromide Mixture
Battistuzzi G, et al.
Advanced Synthesis & Catalysis, 3(349), 297-302 (2007)
A copper-and amine-free Sonogashira coupling reaction promoted by a ferrocene-based phosphinimine-phosphine ligand at low catalyst loading
Arques A, et al.
Tetrahedron Letters, 22(45), 4337-4340 (2004)
Quaternary ammonium acetate: an efficient ionic liquid for the dissolution and regeneration of cellulose
Miao J, et al.
Royal Society of Chemistry Advances, 4(69), 36721-36724 (2014)

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