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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

498327-25ML:
498327-VAR:
498327-BULK:

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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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