Sodium trichloroacetate explained

Sodium trichloroacetate is a chemical compound with a formula of CCl3CO2Na. It is used to increase sensitivity and precision during transcript mapping.[1] It was previously used as an herbicide starting in the 1950s but regulators removed it from the market in the late 1980s and early 1990s.[2] [3] [4] [5]

Preparation

Sodium trichloroacetate is made by reaction trichloroacetic acid with sodium hydroxide:

CCl3CO2H + NaOH -> CCl3CO2Na + H2O

Reactions

Basicity

Sodium trichloroacetate is a weaker base than sodium acetate because of the electron-withdrawing nature of the trichloromethyl group. Sodium trifluoroacetate is likewise a weaker base. However, it can easily be protonated in the presence of suitably strong acids:

CCl3CO2- + H2SO4 -> CCl3CO2H + HSO4-

Trichloromethyl-anion precursor

This reagent is useful for introducing the trichloromethyl group into other molecules. Decarboxylation produces the trichloromethyl anion, which is a sufficiently strong nucleophile to attack various carbonyl functional groups, such as aldehydes, carboxylic acid anhydrides,[6] ketones (making a precursor for the Jocic–Reeve reaction), and acyl halides.

See also

Notes and References

  1. Murray. M. G.. Use of sodium trichloroacetate and mung bean nuclease to increase sensitivity and precision during transcript mapping. Analytical Biochemistry. 158. 1. 165–170. 0003-2697. 2432801. 1986. 10.1016/0003-2697(86)90605-6.
  2. , accessed June 20, 2014
  3. G. S. Rai and C. L. Hamner Persistence of Sodium Trichloroacetate in Different Soil Types Weeds 2(4) Oct. 1953: 271-279
  4. OECD Trichloroacetic Acid CAS N°: 76-03-9 Accessed June 20, 2014
  5. EPA December 1991. trichloroacetic acid (TCA) EPA Cancellation 12/91 Accessed June 20, 2014
  6. Anthony . Winston . John P. M. . Bederka . William G. . Isner . Peter C. . Juliano . John C. . Sharp . J. Org. Chem. . 1965 . 30 . 8 . 2784–2787 . Trichloromethylation of Anhydrides. Ring—Chain Tautomerism . 10.1021/jo01019a068 .