Reaction #4078972
Related Literature (1)
openreactiondata ↗doi:10.1039/C8SC04228D
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-241c5467b31c4d8fbccfc52b801b1825No renderable structure data available
C(=O)(C(C(=O)F)(F)F)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2,2-difluoropropanedioyl difluoride |
|---|---|
| IUPAC Name | — |
| CAS Number | 5930-67-6 |
| Database ID | 2774099 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2,2-difluoropropanedioyl difluoride (CAS 5930-67-6) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 2774099
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
11 reactions · 11 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-241c5467b31c4d8fbccfc52b801b1825Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 1 L monel metal reactor charged with 18 g (0.43 mol) of NaF, 12.1 g (0.112 mol) of CH2(COF)2 was charged with condensation, and thereto, 0.1 g/h of fluorine gas was blown gradually while controlling increasing the inner pressure with keeping the reactor at 0° C., and the reaction was conducted. When the total pressure increased by the product reached to 0.44 atm, the blowing of fluorine gas was finshed. The reaction product was separated and purified, and 1.7 g (0.0118 mol) of CF2(COF)2 was obtained. It was confirmed with FT-IR and 19F-NMR that the resulting compound was CF2(COF)2. The yield thereof was 10%. was charged with condensation while controlling increasing the inner pressure at 0° C. When the total pressure increased by the product The reaction product was separated purified
Source ID: ord-17b2e450575c48c88d007eb0a57546f7Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-241c5467b31c4d8fbccfc52b801b1825Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Methoxytetrafluoropropionyl fluoride (F. S. Fawcett, C. W. Tullock and D. D. Coffman, J. Amer. Chem. Soc., 84, 4275 (1962)) (81 g, 0.45 mol) was slowly added to sulfur trioxide (80 g, 1.0 mol) at 40° C., and the product difluoromalonyl difluoride, bp -9° C., was continuously removed by distillation through a low temperature still, yield 58 g (0.40 mol, 90%). The product structure was confirmed by: λmax 1860 cm-1 (COF), 19F NMR (no solvent), +17.1 ppm (t J=10 Hz) 2F, COF and -114.2 ppm (t J=10 Hz) 2F, CF2. the product difluoromalonyl difluoride, bp -9° C., was continuously removed by distillation through a low temperature still
Source ID: ord-7065c9f392b84b1999c24db01f1d4cc6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Methoxytetrafluoropropionyl fluoride (F. S. Fawcett, C. W. Tullock and D. D. Coffman, J. Amer. Chem. Soc., 84, 4275 (1962)) (81 g, 0.45 mol) was slowly added to sulfur trioxide (80 g, 1.0 mol) at 40° C., and the product difluoromalonyl difluoride, bp -9° C., was continuously removed by distillation through a low temperature still, yield 58 g (0.40 mol, 90%). The product structure was confirmed by: λmax 1860 cm-1 (COF), 19F NMR (no solvent), +17.1 ppm (t J=10 Hz) 2F, COF and -114.2 ppm (t J=10 Hz) 2F, CF2. the product difluoromalonyl difluoride, bp -9° C., was continuously removed by distillation through a low temperature still
Source ID: ord-4aaf57d3b9884f31b0f50d45f0aeebe8Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Methoxytetrafluoropropionyl fluoride (F. S. Fawcett, C. W. Tullock and D. D. Coffman, J. Amer. Chem. Soc., 84, 4275 (1962)) (81 g, 0.45 mol) was slowly added to sulfur trioxide (80 g, 1.0 mol) at 40° C., and the product difluoromalonyl difluoride, bp -9° C., was continuously removed by distillation through a low temperature still, yield 58 g (0.40 mol, 90%). The product structure was confirmed by: λmax 1860 cm-1 (COF), 19F NMR (no solvent), +17.1 ppm (t J=10 Hz), 2F, COF and -114.2 ppm (t J=10 Hz) 2F, CF2. the product difluoromalonyl difluoride, bp -9° C., was continuously removed by distillation through a low temperature still
Source ID: ord-325d9b4ab01649eb8e2c2eedd0c4cd92Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Methoxytetrafluoropropionyl fluoride (F. S. Fawcett, C. W. Tullock and D. D. Coffman, J. Amer. Chem. Soc., 84, 4275 (1962)) (81 g, 0.45 mol) was slowly added to sulfur trioxide (80 g, 1.0 mol) at 40° C., and the product difluoromalonyl difluoride, bp -9° C., was continuously removed by distillation through a low temperature still, yield 58 g (0.40 mol, 90%). The product structure was confirmed by: λmax 1860 cm-1 (COF), 19F NMR (no solvent), +17.1 ppm (t J=10 Hz) 2F, COF and -114.2 ppm (t J=10 Hz) 2F, CF2. the product difluoromalonyl difluoride, bp -9° C., was continuously removed by distillation through a low temperature still
Source ID: ord-e7060104b948402dbaf13a5afc904951Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Methoxytetrafluoropropionyl fluoride (F. S. Fawcett, C. W. Tullock and D. D. Coffman, J. Amer. Chem. Soc., 84, 4275 (1962)) (81 g, 0.45 mol) was slowly added to sulfur trioxide (80 g, 1.0 mol) at 40° C., and the product difluoromalonyl difluoride, bp-9° C., was continuously removed by distillation through a low temperature still, yield 58 g (0.40 mol, 90%). The product structure was confirmed by: λmax 1860 cm-1 (COF), 19F NMR (no solvent), +17.1 ppm (t J=10 Hz) 2F, COF and -114.2 ppm (t J=10 Hz) 2F, CF2. the product difluoromalonyl difluoride, bp-9° C., was continuously removed by distillation through a low temperature still
Source ID: ord-7b672e4534d54d038702eb1112895b53Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 624 g (4.0 mol) of methyl difluorofluoroformylacetate, 348 g (3.5 mol) of fluorosulfonic acid and 25 ml of HSbF6 (0.3 mol) was charged to a 1 liter Teflon® pot fitted with a Teflon® condenser connected to a trap cooled to -80°. The mixture was stirred and heated at 80° to 110° for about 24 h. Then, 187 g (65% yield) of crude difluoromalonyl fluoride was collected which, after trap-to-trap distillation, was analyzed by NMR at -30°. NMR (CCl4): 19F 21.0 (t, JFF 10.9 Hz, 2F, COF) and -112.4 ppm (t, JFF 10.9 Hz, 2F, CF2) with a very small amount of impurity showing at -162.1 ppm. Distillation of a 140 g sample gave 118 g of pure FCOCF2COF, b.p. -4° to -5°. Dimethyl difluoromalonate was also formed. connected to a trap cooled to -80° heated at 80° to 110° for about 24 h
Source ID: ord-e06c4b4a741e424c8372b32805392475Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 84 g (0.54 mol) of methyl difluorofluoroformylacetate, 104 g (1.0 mol) of fluorosulfonic acid and 9 g (0.038 mol) of HSbF6 was heated at 100° to 115° for 20 h. Then, 25.6 g of volatile product, collected through a condenser in a -80° trap, and boiling in the range of -25° to +10°, was identified by IR as difluoromalonyl fluoride (66% yield) based on the stoichiometry 2 FOCCF2CO2CH3 :CF2 (COF)2. Dimethyl difluoromalonate was also formed. was heated at 100° to 115° for 20 h Then, 25.6 g of volatile product, collected through a condenser in a -80° trap boiling in the range of -25° to +10°
Source ID: ord-df175e990a3e46a0aac702a46a1a72a1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 1 L monel metal reactor charged with 18 g (0.43 mol) of NaF, 12.1 g (0.112 mol) of CH2(COF)2 was charged with condensation, and thereto, 0.1 g/h of fluorine gas was blown gradually while controlling increasing the inner pressure with keeping the reactor at 0° C., and the reaction was conducted. When the total pressure increased by the product reached to 0.44 atm, the blowing of fluorine gas was finshed. The reaction product was separated and purified, and 1.7 g (0.0118 mol) of CF2(COF)2 was obtained. It was confirmed with FT-IR and 19F-NMR that the resulting compound was CF2(COF)2. The yield thereof was 10%. was charged with condensation while controlling increasing the inner pressure at 0° C. When the total pressure increased by the product The reaction product was separated purified
Source ID: ord-17b2e450575c48c88d007eb0a57546f7PubChem References
These sources are listed in the compound's public database record.
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