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335991

Tetrabutylammonium acetate

Name: Tetrabutylammonium acetate
Brand: ALDRICH

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:

10534-59-5

Molecular Weight:

301.51

UNSPSC Code:

12352116

NACRES:

NA.22

PubChem Substance ID:

24860355

EC Number:

234-101-8

Beilstein/REAXYS Number:

3599376

MDL number:

MFCD00043208

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Properties

Quality Level

200

assay

97%

form

powder

reaction suitability

core: ammonium

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

Description

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.

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pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

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)

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)

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)

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Global Trade Item Number

SKU	GTIN
335991-10G	04061826742747
335991-50G	04061826742754
335991-5G	04061826742761