Sodium trichloroacetate is a chemical compound with a formula of CCl
3CO
2Na. 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:
:
CCl3CO2H + NaOH -> CCl3CO2Na + H2O
Reactions
Basicity
Sodium trichloroacetate is a weaker base than
sodium acetate
Sodium acetate, CH3COONa, also abbreviated Na O Ac, is the sodium salt of acetic acid. This colorless deliquescent salt has a wide range of uses.
Applications
Biotechnological
Sodium acetate is used as the carbon source for culturing bacteria ...
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
In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they a ...
to attack various
carbonyl
In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containin ...
functional groups, such as
aldehyde
In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group ...
s,
carboxylic acid anhydride
An organic acid anhydride is an acid anhydride that is an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhydride, where the p ...
s,
[{{cite journal , first1= Anthony , last1= Winston , first2= John P. M. , last2= Bederka , first3= William G. , last3= Isner , first4= Peter C. , last4= Juliano , first5= John C. , last5= Sharp , journal= J. Org. Chem. , year= 1965 , volume= 30 , issue= 8 , pages= 2784–2787 , title= Trichloromethylation of Anhydrides. Ring—Chain Tautomerism , doi= 10.1021/jo01019a068 ] ketone
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bon ...
s (making a precursor for the
Jocic–Reeve reaction), and
acyl halide
In organic chemistry, an acyl halide (also known as an acid halide) is a chemical compound derived from an oxoacid by replacing a hydroxyl group () with a halide group (, where X is a halogen).
If the acid is a carboxylic acid (), the compound ...
s.
See also
*
Trichloroacetic acid
Trichloroacetic acid (TCA; TCAA; also known as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms. Salts and esters of trichloroacetic acid are call ...
*
Sodium trifluoroacetate
*
Sodium chloroacetate
References
Organic sodium salts
Trichloromethyl compounds