Methyl trichloroacetate

Methyl trichloroacetate
Methyl trichloroacetate molecule
Names
IUPAC name
Methyl 2,2,2-trichloroacetate[1]
Other names
  • Trichloroacetic acid methyl ester[1]
  • Methyl trichloroethanoate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.056
EC Number
  • 209-960-7
UNII
UN number 2533
  • InChI=1S/C3H3Cl3O2/c1-8-2(7)3(4,5)6/h1H3
    Key: VHFUHRXYRYWELT-UHFFFAOYSA-N
  • COC(=O)C(Cl)(Cl)Cl
Properties
C3H3Cl3O2
Molar mass 177.41 g·mol−1
Appearance Colorless liquid[1]
Odor Sweet, fruity[2]; pungent[3]
Density 1.488 g/mL[4]
Melting point −18 °C (0 °F; 255 K)[4]
Boiling point 152–153 °C (306–307 °F; 425–426 K)[4]
Insoluble[1]
Solubility Soluble in organic solvents[2]
log P 2.03[4]
Vapor pressure 4.3 mmHg[3]
1.455[4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic, serious eye irritation
GHS labelling:
GHS07: Exclamation mark
Warning
H227, H302, H312, H315, H319, H331, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 73 °C (163 °F; 346 K)[4]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Methyl trichloroacetate is an organochlorine compound with the chemical formula CCl3COOCH3. It is a colorless liquid. It is the methyl ester of trichloroacetic acid.

Synthesis

Methyl trichloroacetate can be synthesized by an esterification reaction between trichloroacetic acid and methanol in the presence of an acid as a catalyst (e.g. sulfuric acid).[5]

CCl3COOH + CH3OH → CCl3COOCH3 + H2O

Uses

Methyl trichloroacetate is primarily used in organic synthesis, especially as an intermediate in the production of various pharmaceuticals and agrochemicals.[2]

Reactions

Methyl trichloroacetate methylates carboxylic acids with the loss of chloroform and carbon dioxide.[6] Direct fluorination of liquid methyl trichloroacetate produces fluoromethyl trichloroacetate CCl3COOCH2F and difluoromethyl trichloroacetate CCl3COOCHF2.[7]

Hazards

Methyl trichloroacetate possesses hazards typical of chlorinated organic compounds, including toxicity and environmental hazards. It can cause skin and respiratory irritation and serious eye irritation. It is toxic when inhaled.[1][2]

References

  1. 1 2 3 4 5 PubChem. "Methyl trichloroacetate". pubchem.ncbi.nlm.nih.gov. Retrieved 22 March 2026.
  2. 1 2 3 4 cymitquimica.com. "CAS 598-99-2: Methyl trichloroacetate". cymitquimica.com. Retrieved 22 March 2026.
  3. 1 2 ChemicalBook. "Methyl trichloroacetate". www.chemicalbook.com. Retrieved 22 March 2026.
  4. 1 2 3 4 5 6 Chemical Book. "Methyl trichloroacetate". www.chemicalbook.com. Retrieved 22 March 2026.
  5. ↑ Wang, Y. H.; Wong, P. K. (2005). "Determination of dichloroacetic acid and trichloroacetic acid in drinking water by acidic methanol esterification and headspace gas chromatography". Water Research. 39 (9): 1844–1848. doi:10.1016/j.watres.2005.02.010. PMID 15899282.
  6. ↑ Renga, James M.; Wang, Pen-Chung (1984-01-23). "The Methylation of Carboxylic Acids Using Methyl, Trichloroacetates". Synthetic Communications. 14 (1): 77–82. doi:10.1080/00397918408060867. Retrieved 2026-03-23 – via CrossRef.
  7. ↑ Grakauskas, Vytautas (April 1, 1969). "Direct liquid-phase fluorination of methyl trichloroacetate and acetic anhydride". The Journal of Organic Chemistry. 34 (4): 963–965. doi:10.1021/jo01256a040. Retrieved 2026-03-23.
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