86849

Sigma-Aldrich

Tetrabutylammonium acetate

technical, ≥90% (T)

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

Quality Level

grade

technical

assay

≥90% (T)

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.

Packaging

10, 50 g in glass bottle

Other Notes

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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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)
Tetrabutylammonium Acetate.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
T. Jeffery, M. David
Tetrahedron Letters, 39, 5751-5751 (1998)
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)
Secondary deuterium kinetic isotope effects and the intervention of nonclassical ions in the solvolysis of exo-norborn-2-yl bromobenzene-p-sulfonate.
Maskill H,
Journal of the American Chemical Society, 98(26), 8482-8485 (1976)

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