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 weedkillers, 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 fo ...
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
The trichloromethyl group is a functional group that has the formula –CCl3. The naming of is group is derived from the methyl group (which has the formula –CH3), by replacing each hydrogen atom by a chlorine atom. Compounds with this group are ...
.
Sodium trifluoroacetate
Sodium trifluoroacetate is a chemical compound with a formula of CF3CO2Na. It is the sodium salt of trifluoroacetic acid. It is used as a source of trifluoromethylations.
Basicity
With a pKa of 0.23 for trifluoroacetic acid, the trifluoroaceta ...
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 are ...
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 containing a ...
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 grou ...
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 bo ...
s (making a precursor for the
Jocic–Reeve reaction
In organic chemistry, the Jocic reaction, also called the Jocic–Reeve reaction (named after Zivojin Jocic and Wilkins Reeve) is a name reaction that generates α-substituted carboxylic acids from trichloromethylcarbinols and corresponding nucleop ...
), 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 c ...
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 calle ...
*
Sodium trifluoroacetate
Sodium trifluoroacetate is a chemical compound with a formula of CF3CO2Na. It is the sodium salt of trifluoroacetic acid. It is used as a source of trifluoromethylations.
Basicity
With a pKa of 0.23 for trifluoroacetic acid, the trifluoroaceta ...
*
Sodium chloroacetate
Sodium chloroacetate is the organic compound with the formula CH2ClCO2Na. A white, water-soluble solid, it is the sodium salt of chloroacetic acid. Many of its uses are similar to those of the parent acid. It is prepared by treating chloroacetic ...
References
Organic sodium salts
Trichloromethyl compounds