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E50205

Sigma-Aldrich

Ethyl 4,4,4-trifluoroacetoacetate

99%

Sinonimo/i:

ETFAA, Ethyl 3-oxo-4,4,4-trifluorobutyrate

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5 G
32,10 €
25 G
52,60 €
100 G
111,00 €

32,10 €


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5 G
32,10 €
25 G
52,60 €
100 G
111,00 €

About This Item

Formula condensata:
CF3COCH2CO2C2H5
Numero CAS:
Peso molecolare:
184.11
Beilstein:
608353
Numero CE:
Numero MDL:
Codice UNSPSC:
12352100
ID PubChem:
NACRES:
NA.22

32,10 €


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Livello qualitativo

Saggio

99%

Stato

liquid

Indice di rifrazione

n20/D 1.375 (lit.)

P. ebollizione

129-130 °C (lit.)

Densità

1.259 g/mL at 25 °C (lit.)

Stringa SMILE

CCOC(=O)CC(=O)C(F)(F)F

InChI

1S/C6H7F3O3/c1-2-12-5(11)3-4(10)6(7,8)9/h2-3H2,1H3
OCJKUQIPRNZDTK-UHFFFAOYSA-N

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Applicazioni

Ethyl 4,4,4-trifluoroacetoacetate (ETFAA) is a general reagent to synthesize enantiopure trifluoromethyl-functionalized products.[1] Applications include:
  • Synthesis of (S)- and (R)-α-trifluoromethyl-aspartic acid and α- trifluoromethyl-serine from chiral CF3-oxazolidines, which is derived from ETFAA.[2]
  • Enantiopure synthesis of trifluoromethyl-β-amino acid derivatives.[1]
  • Synthesis of (2R)-2-trifluoromethyl-2-carboxyazetidine, (R)- and (S)-trifluoromethylhomoserines from oxazolidine intermediate obtained by condensing (R)-phenylglycinol with ETFAA.[3]

Pittogrammi

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Avvertenze

Warning

Indicazioni di pericolo

Classi di pericolo

Acute Tox. 4 Oral - Aquatic Chronic 3 - Flam. Liq. 3

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 2

Punto d’infiammabilità (°F)

100.4 °F - closed cup

Punto d’infiammabilità (°C)

38 °C - closed cup

Dispositivi di protezione individuale

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Certificati d'analisi (COA)

Lot/Batch Number

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Concise synthesis of enantiopure (S)-and (R)-α-trifluoromethyl aspartic acid and α-trifluoromethyl serine from chiral trifluoromethyl oxazolidines (Fox) via a Strecker-type reaction.
Simon J, et al.
Tetrahedron Asymmetry, 22(3), 309-314 (2011)
Straightforward Synthesis of Novel Enantiopure α-Trifluoromethylated Azetidine 2-Carboxylic Acid and Homoserines.
Lensen N, et al.
Organic Letters, 17(2), 342-345 (2015)
Ethyl-4, 4, 4-trifluoroacetoacetate (ETFAA), a powerful building block for enantiopure chirons in trifluoromethyl-β-amino acid series.
Michaut V, et al.
Journal of Fluorine Chemistry, 128(8), 889-895 (2007)

Domande

1–2 di 2 domande  
  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 risposta
    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 risposta
    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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