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
Herbicides (, ), also commonly known as weed killers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page f ...
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:
:
Reactions
Basicity
Sodium trichloroacetate is a weaker base than
sodium acetate
Sodium acetate, CH3COONa, also abbreviated Sodium, NaOxygen, OAcetyl, Ac, is the sodium Salt (chemistry), salt of acetic acid. This salt is colorless, deliquescent, and hygroscopy, hygroscopic.
Applications
Biotechnological
Sodium acetate is u ...
because of the electron-withdrawing nature of the
trichloromethyl group
The trichloromethyl group is a functional group that has the chemical formula, formula . The naming of is group is derived from the methyl group (which has the formula ), by replacing each hydrogen atom by a chlorine atom. Compounds with this grou ...
.
Sodium trifluoroacetate is likewise a weaker base. However, it can easily be protonated in the presence of suitably strong acids:
:
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 are ...
to attack various
carbonyl
In organic chemistry, a carbonyl group is a functional group with the formula , composed of a carbon atom double bond, double-bonded to an oxygen atom, and it is divalent at the C atom. It is common to several classes of organic compounds (such a ...
functional groups, such as
aldehyde
In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...
s,
carboxylic acid anhydride
An organic acid anhydride is an acid anhydride that is also an organic compound. An acid anhydride is a compound that has two acyl groups chemical bond, bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhyd ...
s,
ketone
In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...
s (making a precursor for the
Jocic–Reeve reaction), and
acyl halides.
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 cal ...
*
Sodium trifluoroacetate
*
Sodium chloroacetate
Sodium chloroacetate is the organic compound with the formula CH2ClCO2Na. A white, water-soluble solid, it is the sodium Salt (chemistry), salt of chloroacetic acid. Many of its uses are similar to those of the parent acid. It is prepared by tre ...
References
{{Reflist
Organic sodium salts
Trichloromethyl compounds