Trichloroacetyl chloride

Trichloroacetyl chloride
Structural formula
Structural formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
Trichloroacetyl chloride
Other names
2,2,2-Trichloroacetyl chloride
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.843
EC Number
  • 200-926-7
PubChem CID
UNII
UN number 2442
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2Cl4O/c3-1(7)2(4,5)6 checkY
    Key: PVFOMCVHYWHZJE-UHFFFAOYSA-N checkY
  • InChI=1/C2Cl4O/c3-1(7)2(4,5)6
    Key: PVFOMCVHYWHZJE-UHFFFAOYAJ
SMILES
  • ClC(Cl)(Cl)C(Cl)=O
Properties
Chemical formula
C2Cl4O
Molar mass 181.832 g/mol
Density 1.62 g/cm3 at 20 °C
Boiling point 117.9 °C (244.2 °F; 391.0 K)
Solubility miscible with diethyl ether[1]
Thermochemistry
Std enthalpy of
formation fH298)
−280.0 kJ•mol−1[2]
Hazards
GHS labelling:[3]
Pictograms
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Signal word
Danger
Hazard statements
H302, H314, H330
Precautionary statements
P260, P264, P270, P271, P280, P284, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P320, P330, P363, P403+P233, P405
Safety data sheet (SDS) Oxford MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Trichloroacetyl chloride is the acyl chloride of trichloroacetic acid. It can be formed by reacting chlorine with acetyl chloride or acetaldehyde in the presence of activated charcoal, or by the isomerisation of tetrachloroethylene oxide via heating. It is used in the manufacture of pharmaceuticals and plant protection compounds.[4]

References

  1. ^ Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, Florida: CRC Press, pp. 3–536, ISBN 0-8493-0594-2
  2. ^ Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, Florida: CRC Press, pp. 5–29, ISBN 0-8493-0594-2
  3. ^ "Trichloroacetyl chloride". pubchem.ncbi.nlm.nih.gov. Retrieved 12 December 2021.
  4. ^ US Patent No. 5,659,078 to Ebmeyer et al., "Process for the preparation of trichloroacetyl chloride," issued August 19, 1997 (as reproduced by freepatentsonline.com and retrieved on October 23, 2007).