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809071

3-Propyl-3-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-1,5-dioxaspiro[5.5]undecane-2,4-dione

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About This Item

Empirical Formula (Hill Notation):
C19H17F7O4
CAS Number:
1632145-44-8
Molecular Weight:
442.32
NACRES:
NA.22
PubChem Substance ID:
329769136
UNSPSC Code:
12352200
MDL number:
MFCD28359687
Form:
powder
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form

powder

mp

70 °C

storage temp.

2-8°C

SMILES string

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

InChI

1S/C19H17F7O4/c1-2-6-18(15(27)29-17(30-16(18)28)7-4-3-5-8-17)9-11(20)13(22)10(19(24,25)26)14(23)12(9)21/h2-8H2,1H3

InChI key

GQONRLKFRLHMSB-UHFFFAOYSA-N

General description

3-Propyl-3-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-1,5-dioxaspiro[5.5]undecane-2,4-dione is a perfluorinated organic building block. It can be prepared by reacting octafluorotoluene, 3-propyl-1,5-dioxaspiro[5.5]-undecane-2,4-dione, N,N-diisopropylethylamine and CH3CN.

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

12 - Non Combustible Liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBZ2630V

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Weaver Group – Professor Product Portal

Organofluorine chemistry is an essential part of drug discovery programs as well as agrochemical programs and even plays a major role in materials chemistry. Despite the undeniable importance of fluorinated organic molecules, our ability to synthesize these substrates is lacking - though arguably it is better than that of Nature. Consequently, methods that allow facile access to fluorinated molecules are important especially when they provide unique access to fluorinated chemical space.

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

Global Trade Item Number

SKUGTIN
809071-250MG04061833243961