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:
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:
Heating induces decarboxylation and hydrolysis, yielding chloroform and sodium bicarbonate:
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, 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.
In the laboratory, it is used to increase sensitivity and precision during transcript mapping.
Safety Its use as a herbicide is regulated., accessed June 20, 2014G. S. Rai and C. L. Hamner Persistence of Sodium Trichloroacetate in Different Soil Types Weeds 2(4) Oct. 1953: 271-279OECD Trichloroacetic Acid CAS N°: 76-03-9 Accessed June 20, 2014EPA December 1991. trichloroacetic acid (TCA) EPA Cancellation 12/91 Accessed June 20, 2014 The compound has a halflife of week in soils. It is of modest toxicity, with an LD50 (oral, rats) of grams/kg.
See also
Sodium chloroacetate
References