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Merck

335991

Sigma-Aldrich

Tetrabutylammonium acetate

97%

Sinónimos:

N,N,N-tributyl-1-butanaminium acetate, Tetra-n-butylammonium acetate

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About This Item

Fórmula lineal:
(CH3CH2CH2CH2)4N(OCOCH3)
Número de CAS:
Peso molecular:
301.51
Beilstein:
3599376
Número CE:
Número MDL:
Código UNSPSC:
12352116
ID de la sustancia en PubChem:
NACRES:
NA.22
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Nivel de calidad

Ensayo

97%

mp

95-98 °C (lit.)

cadena SMILES

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

Clave InChI

MCZDHTKJGDCTAE-UHFFFAOYSA-M

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Descripción general

Tetrabutylammonium acetate (TBAA) is a phase transfer catalyst (PTC).

Aplicación

Tetrabutylammonium acetate can be used:
  • To catalyze the alkynylation of carbonyl compounds with trimethylsilylacetylenes providing good yields of propargylic alcohols.[1]
  • Along with tetrabutylammonium bromide (TBAB) as a molten reaction medium in the synthesis of 4-aryl-2-quinolones.[2]
  • As a promoter in the regioselective direct arylation of azoles (1-methylpyrazole, oxazole, and thiazole) with aryl bromides in presence of palladium acetate catalyst.[3]
  • As an ionic liquid to dissolve cellulose in the presence of DMSO co-solvent.[4]
  • As an activator in the synthesis of disubstituted alkynes through copper-free Sonogashira coupling reaction.[5]

Pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

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

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves


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Certificados de análisis (COA)

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Visite la Librería de documentos

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)
Chemistry Letters (Jpn), 35, 1002-1002 (2006)
Palladium-based catalytic systems for the synthesis of conjugated enynes by Sonogashira reactions and related alkynylations
Doucet H, and Hierso J-C,
Angewandte Chemie (International Edition in English), 46(6), 834-871 (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)

Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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