Oxalyl fluoride

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Oxalyl fluoride
Structural formula of oxalyl fluoride Oxalyl fluoride.svg
Structural formula of oxalyl fluoride
Ball-and-stick model of oxalyl fluoride Oxalyl-fluoride-3D-balls.png
Ball-and-stick model of oxalyl fluoride
Names
Preferred IUPAC name
Oxalyl difluoride
Other names
TL-108
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.029 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 206-630-4
PubChem CID
UNII
  • InChI=1/C2F2O2/c3-1(5)2(4)6
  • C(=O)(C(=O)F)F
Properties
C2F2O2
Molar mass 94.017 g/mol
Melting point −3 °C (27 °F; 270 K)
Boiling point 26.6 °C (79.9 °F; 299.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Oxalyl fluoride is the organofluorine compound with the formula (COF)2. It is a fluorinated derivative of oxalic acid. This colorless liquid is prepared by reaction of sodium fluoride with oxalyl chloride. [1]

Oxalyl fluoride is being investigated for use in etching as a replacement for compounds which have the liability of high global warming potential. [2] [3]

See also

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Fluoride is an inorganic, monatomic anion of fluorine, with the chemical formula F
, whose salts are typically white or colorless. Fluoride salts typically have distinctive bitter tastes, and are odorless. Its salts and minerals are important chemical reagents and industrial chemicals, mainly used in the production of hydrogen fluoride for fluorocarbons. Fluoride is classified as a weak base since it only partially associates in solution, but concentrated fluoride is corrosive and can attack the skin.

The Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol is oxidized to an aldehyde or ketone using oxalyl chloride, dimethyl sulfoxide (DMSO) and an organic base, such as triethylamine. It is one of the many oxidation reactions commonly referred to as 'activated DMSO' oxidations. The reaction is known for its mild character and wide tolerance of functional groups.

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Iron(III) chloride Inorganic compound

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Sodium fluoride Chemical compound

Sodium fluoride (NaF) is an inorganic compound with the formula NaF. It is used in trace amounts in the fluoridation of drinking water, in toothpaste, in metallurgy, and as a flux, and is also used in pesticides and rat poison. It is a colorless or white solid that is readily soluble in water. It is a common source of fluoride in the production of pharmaceuticals and is used to prevent dental cavities.

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Oxalyl chloride Chemical compound

Oxalyl chloride is an organic chemical compound with the formula (COCl)2. This colorless, sharp-smelling liquid, the diacyl chloride of oxalic acid, is a useful reagent in organic synthesis.

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2
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References

  1. C. W. Tullock, D. D. Coffman (1960). "Synthesis of Fluorides by Metathesis with Sodium Fluoride". J. Org. Chem. 25 (11): 2016–2019. doi:10.1021/jo01081a050.
  2. Method of etching and cleaning using fluorinated carbonyl compounds, US Patent 6635185.
  3. Simon Karecki; Ritwik Chatterjee; Laura Pruette; Rafael Reif; Terry Sparks; Laurie Beu; Victor Vartanian & Konstantin Novoselovc (2001). "Evaluation of Oxalyl Fluoride for a Dielectric Etch Application in an Inductively Coupled Plasma Etch Tool". J. Electrochem. Soc. 148 (3): G141–G149. Bibcode:2001JElS..148G.141K. doi:10.1149/1.1348263.