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809209

Sigma-Aldrich

4-(2,4-Dioxo-3-propyl-1,5-dioxaspiro[5.5]-undecan-3-yl)-2,3,5,6-tetrafluorobenzonitrile

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About This Item

Empirical Formula (Hill Notation):
C19H17F4NO4
CAS Number:
1632145-41-5
Molecular Weight:
399.34
MDL number:
MFCD28359685
UNSPSC Code:
12352200
PubChem Substance ID:
329769147
NACRES:
NA.22

form

powder

storage temp.

2-8°C

SMILES string

FC1=C(F)C(C#N)=C(F)C(F)=C1C2(CCC)C(OC3(CCCCC3)OC2=O)=O

InChI

1S/C19H17F4NO4/c1-2-6-19(11-14(22)12(20)10(9-24)13(21)15(11)23)16(25)27-18(28-17(19)26)7-4-3-5-8-18/h2-8H2,1H3

InChI key

YAKREKYYFSATAN-UHFFFAOYSA-N

General description

4-(2,4-Dioxo-3-propyl-1,5-dioxaspiro[5.5]-undecan-3-yl)-2,3,5,6-tetrafluorobenzonitrile is a substituted Meldrum′s acid derivative. It can be prepared by reacting pentafluorobenzonitrile with 3-propyl-1,5-dioxaspiro[5.5]-undecane-2,4-dione.

Application

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

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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