Sodium trichloroacetate
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| Names | |
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| Preferred IUPAC name
Sodium trichloroacetate | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.010.437 |
| EC Number |
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PubChem CID |
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| RTECS number |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C2Cl3NaO2 | |
| Molar mass | 185.36 g·mol−1 |
| Appearance | White powder |
| Density | ~1.5 g/mL−1 |
| Melting point | 200 °C (392 °F; 473 K) |
| Boiling point | Decomposes |
| 55 g / 100 ml | |
| Solubility | Soluble in methanol and ethanol, slightly soluble in acetone, not soluble in ethers and hydrocarbons |
| Acidity (pKa) | 0.7 (conjugate acid) |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Corrosive |
| GHS labelling: | |
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| Warning | |
| H335, H410 | |
| P261, P271, P273, P304+P340, P312, P391, P403+P233, P405, P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | Non-flammable |
| Non-flammable | |
| Related compounds | |
Other anions |
Sodium trifluoroacetate |
Other cations |
Trichloroacetic acid |
Related compounds |
Sodium chloroacetate Sodium acetate |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
Sodium trichloroacetate is a chemical compound with a formula of CCl3CO2Na. It is a colorless, water-soluble solid.
Preparation
Sodium trichloroacetate is made by the neutralization of trichloroacetic acid with sodium hydroxide:
- CCl3CO2H + NaOH → CCl3CO2Na + H2O
Reactions
Sodium trichloroacetate is a weaker base than sodium acetate because of the electron-withdrawing nature of the trichloromethyl group. Sodium trifluoroacetate is likewise an even weaker base. Sodium trichloroacetate can easily be protonated with suitably strong acids:
- CCl3CO−2 + H2SO4 → CCl3CO2H + HSO−4
Heating induces decarboxylation and hydrolysis, yielding chloroform and sodium bicarbonate:[1] CCl3CO2Na + H2O → HCCl3 + NaHCO3
Under anhydrous conditions, thermal decarboxylation produces the trichloromethyl anion, which is a sufficiently nucleophilic to add to carbonyl functional groups in aldehydes, carboxylic acid anhydrides,[2] ketones, and acyl halides. It is thus a precursor for the Jocic–Reeve reaction.
Applications
Sodium trichloroacetate is a commercial herbicide. It is also used in the dye industry.[1]
In the laboratory, it is used to increase sensitivity and precision during transcript mapping.[3]
Safety
Its use as a herbicide is regulated.[4][5][6][7] The compound has a halflife of week in soils. It is of modest toxicity, with an LD50 (oral, rats) of grams/kg.[1]
See also
References
- 1 2 3 Koenig, Günter; Lohmar, Elmar; Rupprich, Norbert (2000). "Chloroacetic Acids". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a06_537. ISBN 3-527-30673-0.
- ↑ Winston, Anthony; Bederka, John P. M.; Isner, William G.; Juliano, Peter C.; Sharp, John C. (1965). "Trichloromethylation of Anhydrides. Ring—Chain Tautomerism". J. Org. Chem. 30 (8): 2784–2787. doi:10.1021/jo01019a068.
- ↑ Murray, M. G. (1986). "Use of sodium trichloroacetate and mung bean nuclease to increase sensitivity and precision during transcript mapping". Analytical Biochemistry. 158 (1): 165–170. doi:10.1016/0003-2697(86)90605-6. ISSN 0003-2697. PMID 2432801.
- ↑ TCA-sodium in the Pesticide Properties DataBase (PPDB), accessed June 20, 2014
- ↑ G. S. Rai and C. L. Hamner Persistence of Sodium Trichloroacetate in Different Soil Types Weeds 2(4) Oct. 1953: 271-279
- ↑ OECD Trichloroacetic Acid CAS N°: 76-03-9 Archived 2016-03-04 at the Wayback Machine Accessed June 20, 2014
- ↑ EPA December 1991. trichloroacetic acid (TCA) EPA Cancellation 12/91 Accessed June 20, 2014