Sodium trichloroacetate

Sodium trichloroacetate
Names
	Preferred IUPAC name Sodium trichloroacetate
Identifiers
CAS Number	650-51-1;
3D model (JSmol)	Interactive image;
ChemSpider	12073;
ECHA InfoCard	100.010.437
EC Number	211-479-2;
PubChem CID	23681045;
RTECS number	AJ9100000;
UNII	2N76A3BRJ0;
CompTox Dashboard (EPA)	DTXSID6034924 ;
	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)[O-])(Cl)(Cl)Cl.[Na+];
Properties
Chemical formula	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
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
Signal word	Warning
Hazard statements	H335, H410
Precautionary statements	P261, P271, P273, P304+P340, P312, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)	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 [77 °F], 100 kPa). Infobox references

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:

{\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:

{\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,[6] ketones (making a precursor for the Jocic–Reeve reaction), and acyl halides.

References

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
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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[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.