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Sigma-Aldrich

Tetrabutylammonium acetate

technical, ≥90% (T)

Synonym(s):

TBAAc

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About This Item

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:
57653198
NACRES:
NA.22

grade

technical

Quality Level

100

Assay

≥90% (T)

form

powder

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 is an effective alternative for sodium acetate (NaOAc) due to its good solubility in organic solvents.

Application

Tetrabutylammonium acetate (TBAAc) is a good source of nucleophilic acetate ion for SN2 substitution reactions. It is commonly used to displace sulfonates and allylic halides to get corresponding acetates. Additionally, TBAAc can also be used as a mild, soluble base in Sonogashira reaction and Heck arylation.

Other Notes

Reagent for the epimerization of hydroxyl groups; base-molten salt for directing Heck-type reactions

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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Ligand-, copper-, and amine-free Sonogashira reaction of aryl iodides and bromides with terminal alkynes.
Urgaonkar S and Verkade JG
The Journal of Organic Chemistry, 69(17), 5752-5755 (2004)
Pd nanoparticle catalyzed Heck arylation of 1, 1-disubstituted alkenes in ionic liquids. Study on factors affecting the regioselectivity of the coupling process.
Calo V, et al.
Organometallics, 22(21), 4193-4197 (2003)
T. Jeffery, M. David
Tetrahedron Letters, 39, 5751-5751 (1998)
T. Jeffery
Tetrahedron Letters, 40, 1673-1673 (1999)
G. Battistuzzi et al.
Synlett, 439-439 (2002)
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