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498327

Sigma-Aldrich

Ethyl 2-fluoroacetoacetate

Synonym(s):

2-Fluoro-3-oxobutanoic acid ethyl ester, Ethyl 2-fluoro-3-oxobutanoate, Ethyl 2-fluoro-3-oxobutyrate, NSC 24563

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About This Item

Linear Formula:
CH3COCH(F)CO2C2H5
CAS Number:
1522-41-4
Molecular Weight:
148.13
MDL number:
MFCD00215830
UNSPSC Code:
12352100
PubChem Substance ID:
24873190

refractive index

n20/D 1.414 (lit.)

bp

183 °C (lit.)

density

1.181 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/C6H9FO3/c1-3-10-6(9)5(7)4(2)8/h5H,3H2,1-2H3

InChI key

SHTFQLHOTAJQRJ-UHFFFAOYSA-N

General description

Ethyl 2-fluoroacetoacetate is an α-fluorinated β-keto ester that can be prepared by the fluorination of ethyl acetoacetate.

Application

Ethyl 2-fluoroacetoacetate may be used in the preparation of:
  • δ-keto-β-hydroxy-α-fluoro esters
  • fluorinated [1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-ones
  • fluorinated [1,2,4]triazolo[5,1-c][1,2,4]triazin-4(1H)-ones
  • 4-fluorofarnesol
Reactant for:
  • Michael addition-induced cyclization reaction
  • Asymmetric Mannich reaction
  • Enantioselective organocatalytic conjugate addition

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

194.0 °F - closed cup

Flash Point(C)

90 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBS8874V
BCBK4199V
1431241V
BCBD8942V
1431241

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Fluorinated [1,2,4] triazolo [1,5-a] pyrimidines and [1,2,4] triazolo [5,1-c][1,2,4] triazines*.
Ulomskiy EN, et al.
Chemistry of Heterocyclic Compounds, 47(9), 1164-1169 (2011)
Fluoroisoprenyl synthesis using ethyl 2-fluoroacetoacetate.
Ortiz de Montellano PR and Vinson WA.
The Journal of Organic Chemistry, 42(11), 2013-2014 (1977)
Green chemistry: synthesis in micro reactors.
Haswell SJ and Watts P.
Green Chemistry, 5(2), 240-249 (2003)
Organocatalytic direct aldol reaction between acetone and α-substituted β-keto esters.
London G, et al.
J. Mol. Catal. A: Chem., 267(1), 98-101 (2007)

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