diethyl 2,2-difluoropentanedioate

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diethyl 2,2-difluoropentanedioate manufacturers

diethyl 2,2-difluoropentanedioate Basic information
Product Name:diethyl 2,2-difluoropentanedioate
Synonyms:diethyl 2,2-difluoropentanedioate;Pentanedioic acid, 2,2-difluoro-, 1,5-diethyl ester
CAS:428-97-7
MF:C9H14F2O4
MW:224.2
EINECS:
Product Categories:
Mol File:428-97-7.mol
diethyl 2,2-difluoropentanedioate Structure
diethyl 2,2-difluoropentanedioate Chemical Properties
Boiling point 127-128 °C(Press: 28 Torr)
density 1.149±0.06 g/cm3(Predicted)
storage temp. 2-8°C
InChIInChI=1S/C9H14F2O4/c1-3-14-7(12)5-6-9(10,11)8(13)15-4-2/h3-6H2,1-2H3
InChIKeyYVPKMLFMDHSTKJ-UHFFFAOYSA-N
SMILESC(OCC)(=O)C(F)(F)CCC(OCC)=O
Safety Information
HS Code 2918199890
MSDS Information
diethyl 2,2-difluoropentanedioate Usage And Synthesis
Synthesis
Ethyl bromodifluoroacetate

667-27-6

Ethyl acrylate

140-88-5

diethyl 2,2-difluoropentanedioate

428-97-7

General procedure for the synthesis of diethyl 2,2-difluoroglutarate from ethyl bromodifluoroacetate and ethyl acrylate: copper powder (700 mg) and tetrahydrofuran (5.8 mL) were added to the reaction vessel and stirred at 50 °C. Ethyl acrylate (0.50 g), ethyl bromodifluoroacetate (2.53 g), TMEDA (0.29 g) and acetic acid (0.27 g) were then added sequentially. The reaction was terminated after 0.5 hrs. To the reaction mixture was added 10% aqueous ammonium chloride solution, filtered through a diatomaceous earth pad to remove the copper residue, and the filtrate was extracted with methyl tert-butyl ether to afford diethyl 2,2-difluoroglutarate (1.09 g, 97.4% yield). Alternatively, diethyl 2,2-difluoroglutarate (1.08 g, 96.4% yield) was obtained by following the same method as described above except that water (0.10 g) was used instead of acetic acid.

References[1] Patent: CN104159884, 2016, B. Location in patent: Paragraph 0060; 0061; 0062; 0063; 0064
[2] Synthesis, 2012, vol. 44, # 20, p. 3165 - 3170,6
[3] Patent: WO2009/82134, 2009, A2. Location in patent: Page/Page column 41-42
[4] Patent: WO2012/30106, 2012, A2. Location in patent: Page/Page column 11
[5] Patent: US2013/165659, 2013, A1. Location in patent: Paragraph 0098; 0099; 0100
diethyl 2,2-difluoropentanedioate Preparation Products And Raw materials
Raw materialsSodium ethoxide-->Ethyl bromodifluoroacetate-->Ethyl acrylate-->Cyclopentene, 3,3-difluoro--->N,N,N',N'-Tetramethylethylenediamine-->Copper-->Acetic acid-->Tetrahydrofuran
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