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Sigma-Aldrich

Tetrabutylammonium acetate

97%

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Synonym(s):
N,N,N-tributyl-1-butanaminium acetate, Tetra-n-butylammonium acetate
Linear Formula:
(CH3CH2CH2CH2)4N(OCOCH3)
CAS Number:
10534-59-5
Molecular Weight:
301.51
Beilstein:
3599376
EC Number:
234-101-8
MDL number:
MFCD00043208
UNSPSC Code:
12352116
PubChem Substance ID:
24860355
NACRES:
NA.22

Quality Level

200

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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 and catalysis, 3(349), 297-302 (2007)
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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