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Merck

E50205

Sigma-Aldrich

4,4,4-Trifluoracetessigsäureethylester

99%

Synonym(e):

3-Oxo-4,4,4-trifluor-buttersäure-ethylester

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About This Item

Lineare Formel:
CF3COCH2CO2C2H5
CAS-Nummer:
Molekulargewicht:
184.11
Beilstein:
608353
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352100
PubChem Substanz-ID:
NACRES:
NA.22
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Assay

99%

Form

liquid

Brechungsindex

n20/D 1.375 (lit.)

bp

129-130 °C (lit.)

Dichte

1.259 g/mL at 25 °C (lit.)

SMILES String

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

InChIKey

OCJKUQIPRNZDTK-UHFFFAOYSA-N

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Anwendung

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]

Piktogramme

FlameExclamation mark

Signalwort

Warning

Gefahreneinstufungen

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

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 2

Flammpunkt (°F)

100.4 °F - closed cup

Flammpunkt (°C)

38 °C - closed cup

Persönliche Schutzausrüstung

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


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Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

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)

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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