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537594

Sigma-Aldrich

tert-Butyl acetoacetate

reagent grade, 98%

Sinônimo(s):

TBAA

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About This Item

Fórmula linear:
CH3COCH2COOC(CH3)3
Número CAS:
1694-31-1
Peso molecular:
158.19
Beilstein:
1680303
Número MDL:
MFCD00008811
Código UNSPSC:
12352100
ID de substância PubChem:
24878235
NACRES:
NA.22
Preço e disponibilidade não estão disponíveis no momento.

grau

reagent grade

Ensaio

98%

Lim. expl.

8 % (lit.)

Impurezas

≤0.20% water
water

índice de refração

n20/D 1.419 (lit.)

p.e.

71-72 °C/11 mmHg (lit.)

pf

-38 °C (lit.)

densidade

0.954 g/mL at 25 °C (lit.)

grupo funcional

ester
ketone

cadeia de caracteres SMILES

CC(=O)CC(=O)OC(C)(C)C

InChI

1S/C8H14O3/c1-6(9)5-7(10)11-8(2,3)4/h5H2,1-4H3

chave InChI

JKUYRAMKJLMYLO-UHFFFAOYSA-N

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Descrição geral

tert-Butyl acetoacetate (t-BAA) is a cheap and easy to store commercial reagent. Reaction demonstrated that the more hindered tert-butyl acetoacetate (t-BAA, la) is ca.15-20-fold more reactive than the more commonly used methyl or ethyl analogs.[1] It is widely employed as an acetoacetylating reagent.[2]

Aplicação

tert-Butyl acetoacetate may be used in the synthesis of:
  • various acetoacetic acid derivatives[1][3]
  • acetoacetates[1]
  • acetoacetamides[1]
  • 1-(diethylamino)-2-acetoacetoxypropane[1]
  • (S)-tert-butyl 3-hydroxybutyrate[4]
  • benzothiazole β-keto ester derivatives[5]
  • 3,4-disubstituted pyrroles[6]

Código de classe de armazenamento

10 - Combustible liquids

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

150.8 °F - closed cup

Ponto de fulgor (°C)

66 °C - closed cup

Equipamento de proteção individual

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificados de análise (COA)

Lot/Batch Number
MKCK4314
MKCB0832V
MKBD4606V
MKBL4718V
MKBD4606

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Visite a Biblioteca de Documentos

Transesterification.
Otera J.
Chemical Reviews, 93(4), 1449-1470 (1993)
Deborah A Smithen et al.
Organic & biomolecular chemistry, 11(1), 62-68 (2012-10-17)
Prodigiosenes, possessing a 4-methoxypyrrolyldipyrrin skeleton, are known for their anti-cancer activity. Structural modification of the C-ring resulted in a series of prodigiosenes that displayed promising activity against leukemia cell lines during in vitro analysis against the NCI 60 cancer cell
Transacetoacetylation with tert-butyl acetoacetate: synthetic applications.
Witzeman JS and Nottingham WD.
The Journal of Organic Chemistry, 56(5), 1713-1718 (1991)
Enzymatic Synergism in the Synthesis of ?-Keto Esters.
Wisniewska C, et al.
European Journal of Organic Chemistry, 24, 5432-5437 (2015)
Highly enantioselective Mannich reactions of imines with tert-butyl acetoacetate catalyzed by squaramide organocatalyst.
He HX and Du DM.
Tetrahedron Asymmetry, 25(8), 637-643 (2014)
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Questions

1–2 of 2 Questions  

  1. 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

      Helpful?

  2. 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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