Chemistry:Methyl trichloroacetate
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Short description: Methyl ester chemical compound
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| Names | |
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| IUPAC name
Methyl 2,2,2-trichloroacetate[1]
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Other names
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| UNII | |
| UN number | 2533 |
CompTox Dashboard (EPA)
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| 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] |
Refractive index (nD)
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1.455[4] |
| Hazards | |
| Main hazards | Toxic, serious eye irritation |
| GHS pictograms | 
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| GHS Signal word | Warning |
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| PP261Script error: No such module "Preview warning".Category:GHS errors, PP264Script error: No such module "Preview warning".Category:GHS errors, PP264+P265Script error: No such module "Preview warning".Category:GHS errors, PP271Script error: No such module "Preview warning".Category:GHS errors, PP280Script error: No such module "Preview warning".Category:GHS errors, PP302+P352Script error: No such module "Preview warning".Category:GHS errors, PP304+P340Script error: No such module "Preview warning".Category:GHS errors, PP305+P351+P338Script error: No such module "Preview warning".Category:GHS errors, PP319Script error: No such module "Preview warning".Category:GHS errors, PP321Script error: No such module "Preview warning".Category:GHS errors, PP332+P317Script error: No such module "Preview warning".Category:GHS errors, PP337+P317Script error: No such module "Preview warning".Category:GHS errors, PP362+P364Script error: No such module "Preview warning".Category:GHS errors, PP403+P233Script error: No such module "Preview warning".Category:GHS errors, PP405Script error: No such module "Preview warning".Category:GHS errors, PP501Script error: No such module "Preview warning".Category:GHS errors | |
| NFPA 704 (fire diamond) | |
| 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 | |
Tracking categories (test):
Methyl trichloroacetate is an organochlorine compound with the chemical formula CCl
3COOCH
3. 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]
- CCl
3COOH + CH
3OH → CCl
3COOCH
3 + H
2O
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 CCl
3COOCH
2F and difluoromethyl trichloroacetate CCl
3COOCHF
2.[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
- ↑ 1.0 1.1 1.2 1.3 1.4 PubChem. "Methyl trichloroacetate". https://pubchem.ncbi.nlm.nih.gov/compound/Methyl-trichloroacetate.
- ↑ 2.0 2.1 2.2 2.3 cymitquimica.com. "CAS 598-99-2: Methyl trichloroacetate". https://cymitquimica.com/cas/598-99-2/.
- ↑ 3.0 3.1 ChemicalBook. "Methyl trichloroacetate". https://www.chemicalbook.com/msds/methyltrichloroacetate.htm.
- ↑ 4.0 4.1 4.2 4.3 4.4 4.5 Chemical Book. "Methyl trichloroacetate". https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7276383.htm.
- ↑ 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. https://www.sciencedirect.com/science/article/abs/pii/S0043135405000783.
- ↑ 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. http://www.tandfonline.com/doi/abs/10.1080/00397918408060867. Retrieved 2026-03-23.
- ↑ 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. https://pubs.acs.org/doi/10.1021/jo01256a040. Retrieved 2026-03-23.
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