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Merck
CN

86849

Tetrabutylammonium acetate

≥90% (T), powder, technical grade

Synonym(s):

TBAAc

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N(OCOCH3)
CAS Number:
10534-59-5
Molecular Weight:
301.51
NACRES:
NA.22
PubChem Substance ID:
57653198
UNSPSC Code:
12352116
EC Number:
234-101-8
MDL number:
MFCD00043208
Beilstein/REAXYS Number:
3599376

Key Documents

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Product Name

Tetrabutylammonium acetate, technical, ≥90% (T)

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

grade

technical

assay

≥90% (T)

form

powder

mp

95-98 °C (lit.)

Quality Level

100

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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.

General description

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

Other Notes

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

pictograms

Exclamation mark
GHS07

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCN9954
BCCN4872
BCCN3471
BCCL7304
BCCK4901

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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)
A.C. Cope et al.
Journal of the American Chemical Society, 87, 3122-3122 (1965)
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