Caesium acetate

Caesium acetate or cesium acetate is an ionic caesium compound with the molecular formula CH3COOCs. It is a white solid that may be formed by the reaction of caesium hydroxide or caesium carbonate with acetic acid.[3]

Caesium acetate[1]

Structural formula
anhydrous caesium acetate crystallizes in a hexagonal unit cell.
Unit cell of anhydrous caesium acetate.
Names
Preferred IUPAC name
Caesium acetate
Other names
Cesium acetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.020.226
UNII
  • InChI=1S/C2H4O2.Cs/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1 checkY
    Key: ZOAIGCHJWKDIPJ-UHFFFAOYSA-M checkY
  • InChI=1/C2H4O2.Cs/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1
    Key: ZOAIGCHJWKDIPJ-REWHXWOFAB
  • [Cs+].[O-]C(=O)C
Properties
C2H3CsO2
Molar mass 191.949 g/mol
Appearance colourless, hygroscopic
Density 2.423 g/cm3, solid
Melting point 194 °C (381 °F; 467 K)
Boiling point 945 °C (1,733 °F; 1,218 K)
945.1 g/100 g (−2.5 °C)
1345.5 g/100 ml (88.5 °C)
Structure[2]
Primitve hexagonal
P6/m, No. 175
a = 1488.0 pm, c = 397.65 pm[2]
76.542 cm3·mol−1
6
Hazards
Flash point Non-flammable
Related compounds
Other anions
 Caesium formate
Other cations
 Lithium acetate
Sodium acetate
Potassium acetate
Rubidium acetate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

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 aldehydes with fatty acids. Replacement of the commonly used sodium acetate with caesium acetate has been shown to improve yields by up to 10 times.[3][4]

It is often used to invert secondary alcohols, first by direct SN2 substitution of the hydroxyl group with acetate, which is then converted back to a hydroxyl group.[3]

Caesium acetate is occasionally used instead of caesium formate in petroleum drilling fluids.

References
  1. Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. B-91. ISBN 0-8493-0462-8..
  2. Lossin, Adalbert; Meyer, Gerd (1993). "Kristallstruktur von Caesiumacetat, Cs(CH3COO)". Zeitschrift für Anorganische und Allgemeine Chemie. 619 (8): 1462–1464. doi:10.1002/zaac.19936190823.
  3. Yode, Ryan (2015), "Cesium Acetate", Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, pp. 1–11, doi:10.1002/047084289x.rn01845, ISBN 978-0-470-84289-8, retrieved 2020-07-21
  4. Koepp, E.; Vögtle, F. (1987), "Perkin-Synthese mit Cäsiumacetat", Synthesis, 1987 (2): 177–179, doi:10.1055/s-1987-27880.

Further reading
  • Torisawa, Yasuhiro; Okabe, Hiromitsu; Ikegami, Shiro (1984), "Efficient Inversions of Secondary Alcohols using Cesium Acetate and 18-Crown-6", Chem. Lett., 13 (9): 1555–56, doi:10.1246/cl.1984.1555.
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