Skip to Content
MilliporeSigma
All Photos(1)

Documents

809136

Sigma-Aldrich

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C18H17F4NO6
CAS Number:
1632145-40-4
Molecular Weight:
419.32
MDL number:
MFCD28359688
UNSPSC Code:
12352202
PubChem Substance ID:
329769141

form

powder

storage temp.

2-8°C

SMILES string

FC1=C(F)C([N+]([O-])=O)=C(F)C(F)=C1C2(CCC)C(OC3(CCCCC3)OC2=O)=O

InChI

1S/C18H17F4NO6/c1-2-6-18(9-10(19)12(21)14(23(26)27)13(22)11(9)20)15(24)28-17(29-16(18)25)7-4-3-5-8-17/h2-8H2,1H3

InChI key

JWAHHCQJIGIGMQ-UHFFFAOYSA-N

General description

3-Propyl-3-(2,3,5,6-tetrafluoro-4-nitrophenyl)-1,5-dioxaspiro[5.5]undecane-2,4-dione can be synthesized from pentafluoronitrobenzene, 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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Related Content

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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service