Chemistry:Sodium trichloroacetate

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Sodium trichloroacetate
Natriumtrichlooracetaat.png
Names
Preferred IUPAC name
Sodium trichloroacetate
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 211-479-2
RTECS number
  • AJ9100000
UNII
Properties
C2Cl3NaO2
Molar mass 185.36 g/mol
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
Main hazards Corrosive
GHS pictograms GHS07: HarmfulGHS09: Environmental hazard
GHS Signal word Warning
H335, H410
P261, P271, P273, P304+340, P312, P391, P403+233, P405, P501
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
3
1
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
Tracking categories (test):

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:

[math]\ce{ CCl3CO2H + NaOH -> CCl3CO2Na + H2O }[/math]

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:

[math]\ce{ CCl3CO2- + H2SO4 -> CCl3CO2H + HSO4- }[/math]

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

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 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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