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809268

Sigma-Aldrich

N-Ethyl-N-isopropylpropan-2-aminium 4-Oxo-3-(perfluoropyridin-4-yl)-1,5-dioxaspiro[5.5]undec-2-en-2-olate

≥95%

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About This Item

Empirical Formula (Hill Notation):
C22H30F4N2O4
CAS Number:
1632145-10-8
Molecular Weight:
462.48
UNSPSC Code:
12352200
PubChem Substance ID:
329769151
NACRES:
NA.22

Assay

≥95%

form

powder

mp

134-139 °C

storage temp.

2-8°C

SMILES string

CC([NH+](CC)C(C)C)C.[O-]C(OC1(CCCCC1)O2)=C(C3=C(F)C(F)=NC(F)=C3F)C2=O

InChI

1S/C14H11F4NO4.C8H19N/c15-8-6(9(16)11(18)19-10(8)17)7-12(20)22-14(23-13(7)21)4-2-1-3-5-14;1-6-9(7(2)3)8(4)5/h20H,1-5H2;7-8H,6H2,1-5H3

InChI key

RCRKIJBXPWODMA-UHFFFAOYSA-N

General description

N-Ethyl-N-isopropylpropan-2-aminium 4-oxo-3-(perfluoropyridin-4-yl)-1,5-dioxaspiro[5.5]undec-2-en-2-olate is a fluoroarylated-Meldrum′s acid adduct. It can be prepared by reacting pentafluoropyridine with cyclohexyl-Meldrum′s acid in the presence of N,N-diisopropylethylamine and acetonitrile.

Application

N-Ethyl-N-isopropylpropan-2-aminium 4-oxo-3-(perfluoropyridin-4-yl)-1,5-dioxaspiro[5.5]undec-2-en-2-olate may be used to synthesize ethyl 2-(2-(perfluoropyridin-4-yl)acetamido)-acetate and N-methoxy-N-methyl-2-(perfluoropyridin-4-yl)-acetamide.
This compound undergoes cycloreversion to form the fluoro(hetero)aryl ketene, which undergoes efficient coupling with nucleophiles and allows rapid incorporation of highly fluorinated α-fluoro(hetero)aryl acetic acid derivatives.

Other Notes

Selective Perfluoro- and Polyfluoroarylation of Meldrum′s Acid

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P305 + P351 + P338

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Sameera M Senaweera et al.
The Journal of organic chemistry, 79(21), 10466-10476 (2014-10-02)
This work describes the facile and mono-selective per- and polyfluoroarylation of Meldrum's acid to generate a versatile synthon for highly fluorinated α-phenyl acetic acid derivatives, which provide straightforward access to fluorinated building blocks. The reaction takes place quickly, and most

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