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Sodium trichloroacetate

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Sodium trichloroacetate
Names
Preferred IUPAC name Sodium trichloroacetate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.437 Edit this at Wikidata
EC Number
  • 211-479-2
PubChem CID
RTECS number
  • AJ9100000
UNII
CompTox Dashboard (EPA)
InChI
  • Key: SAQSTQBVENFSKT-UHFFFAOYSA-M
  • InChI=1S/C2HCl3O2.Na/c3-2(4,5)1(6)7;/h(H,6,7);/q;+1/p-1
SMILES
  • C(C(=O))(Cl)(Cl)Cl.
Properties
Chemical formula C2Cl3NaO2
Molar mass 185.36 g/mol
Appearance White powder
Density ~1.5 g/mL
Melting point 200 °C (392 °F; 473 K)
Boiling point Decomposes
Solubility in water 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:
Pictograms GHS07: Exclamation markGHS09: Environmental hazard
Signal word Warning
Hazard statements H335, H410
Precautionary statements P261, P271, P273, P304+P340, P312, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3 1 1
Flash point Non-flammable
Autoignition
temperature 		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 , 100 kPa). Infobox references
Chemical compound

Sodium trichloroacetate is a chemical compound with a formula of CCl3CO2Na. It is used to increase sensitivity and precision during transcript mapping. 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.

Preparation

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

CCl 3 CO 2 H + NaOH ⟶ CCl 3 CO 2 Na + H 2 O {\displaystyle {\ce {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:

CCl 3 CO 2 − + H 2 SO 4 ⟶ CCl 3 CO 2 H + HSO 4 − {\displaystyle {\ce {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, ketones (making a precursor for the Jocic–Reeve reaction), and acyl halides.

See also

References

  1. 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.
  2. TCA-sodium in the Pesticide Properties DataBase (PPDB), 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 Archived 2016-03-04 at the Wayback Machine Accessed June 20, 2014
  5. EPA December 1991. trichloroacetic acid (TCA) EPA Cancellation 12/91 Accessed June 20, 2014
  6. 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.
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