Caesium acetate or cesium acetate is an
ionic
caesium
Caesium (IUPAC spelling) (or cesium in American English) is a chemical element with the symbol Cs and atomic number 55. It is a soft, silvery-golden alkali metal with a melting point of , which makes it one of only five elemental metals that a ...
compound with the molecular formula CH
3COOCs. It is a white solid that may be formed by the reaction of
caesium hydroxide
Caesium hydroxide is a strong base (pKa= 15.76) containing the highly reactive alkali metal caesium, much like the other alkali metal hydroxides such as sodium hydroxide and potassium hydroxide. Caesium hydroxide is corrosive enough to quickly ...
or
caesium carbonate
Caesium carbonate or cesium carbonate is a white crystalline solid compound. Caesium carbonate has a high solubility in polar solvents such as water, alcohol and DMF. Its solubility is higher in organic solvents compared to other carbonates l ...
with
acetic acid
Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main componen ...
.
Uses
It is used in organic synthesis. One example is in the
Perkin synthesis: the formation of
unsaturated cinnamic-type acids by the condensation of aromatic
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 gro ...
s with
fatty acid
In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, f ...
s. Replacement of the commonly used sodium acetate with caesium acetate has been shown to improve yields by up to 10 times.
[.]
It is often used to invert secondary alcohols, first by direct
SN2 substitution of the
hydroxyl group
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...
with acetate, which is then converted back to a hydroxyl group.
Caesium acetate is occasionally used instead of caesium formate in petroleum drilling fluids.
References
Further reading
*.
External links
Caesium acetate factsheet from Chemetall GmbH
{{Acetates
Caesium compounds
Acetates
Reagents for organic chemistry