Fluoroacetyl chloride

Fluoroacetyl chloride
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
Fluoroacetyl chloride
Other names
2-Fluoroacetyl chloride
Fluoroethanoyl chloride
Identifiers
CAS Number
  • 359-06-8 checkY=
3D model (JSmol)
  • Interactive image
ChemSpider
  • 9282 ☒N
ECHA InfoCard 100.006.022 Edit this at Wikidata
PubChem CID
  • 9663
UNII
  • 0CQX1ANG4H checkY
CompTox Dashboard (EPA)
  • DTXSID4059885 Edit this at Wikidata
InChI
  • InChI=1S/C2H2ClFO/c3-2(5)1-4/h1H2 ☒N
    Key: ZBHDTYQJAQDBIH-UHFFFAOYSA-N ☒N
  • InChI=1/C2H2ClFO/c3-2(5)1-4/h1H2
    Key: ZBHDTYQJAQDBIH-UHFFFAOYAI
  • FCC(Cl)=O
Properties
Chemical formula
 C2H2ClFO
Molar mass 96.49 g·mol−1
Boiling point 70 to 71 °C (158 to 160 °F; 343 to 344 K) at 755 mmHg[1]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
4
1
2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references
Chemical compound

Fluoroacetyl chloride is an acyl chloride.

In 1948, William E. Truce of Purdue University described a synthesis of fluoroacetyl chloride which was undertaken "because of its potential value for introducing the group, —COCH2F, into organic molecules."[1] In this synthesis, he reacted sodium fluoroacetate with phosphorus pentachloride to obtain the desired compound.

See also

  • Fluoroacetic acid
  • Methyl fluoroacetate

References

  1. ^ a b Truce, William E. (August 1948). "The Preparation of Fluoroacetyl Chloride". Journal of the American Chemical Society. 70 (88): 2828. doi:10.1021/ja01188a524.
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Derivatives of fluoroacetic acid and 2-fluoroethanol
Fluoroacetate salts
  • Aluminum fluoroacetate
  • Ammonium fluoroacetate
  • Barium fluoroacetate
  • Cadmium fluoroacetate
  • Calcium fluoroacetate
  • Cupric fluoroacetate
  • Potassium fluoroacetate
  • Sodium fluoroacetate
  • Thallous fluoroacetate
  • Triethyllead fluoroacetate
Fluoroacetate esters
Fluoroethyl esters
  • Bis(2-fluoroethyl) carbonate
  • Bis(2-fluoroethyl) hydrogen phosphite
  • Bis(2-fluoroethyl) phosphorofluoridate
  • Bis(2-fluoroethyl) sulfate
  • Bis(2-fluoroethyl) sulfite
  • Fluenetil
  • Fluoroethyl acetate
  • Fluoroethyl chloroacetate
  • Fluoroethyl chloroformate
  • Fluoroethyl chlorosulfonate
  • Fluoroethyl fluoroacetate
  • Fluoroethyl nitrite
  • Fluoroethyl trichloroacetate
  • Tetrakis(2-fluoroethyl) orthosilicate
  • TL-790
  • TL-821
  • Tris(2-fluoroethyl) arsenite
  • Tris(2-fluoroethyl) borate
  • Tris(2-fluoroethyl) phosphite
  • Tris(2-fluoroethyl) orthoformate
Fluoroacetamides
Other
  • Bis(2-fluoroethyl)ether
  • 2-chloroethyl fluorothioacetate
  • Fluoroacetic anhydride
  • Fluoroacetyl chloride
  • Fluoroacetyl fluoride


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