Caesium acetate

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
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.020.226
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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
SMILES
  • [Cs+].[O-]C(=O)C
Properties
Chemical formula
 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)
Solubility in water
 945.1 g/100 g (−2.5 °C)
1345.5 g/100 ml (88.5 °C)
Structure[2]
Crystal structure
 Primitive hexagonal
Space group
 P6/m, No. 175
Lattice constant
a = 1488.0 pm, c = 397.65 pm[2]
Lattice volume (V)
 76.542 cm3·mol−1
Formula units (Z)
 6
Hazards
GHS labelling:[3]
Pictograms
 GHS07: Exclamation markGHS08: Health hazard
Signal word
 Warning
Hazard statements
 H302, H319, H361f, H373
Precautionary statements
 P203, P260, P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P318, P319, P330, P337+P317, P405, P501
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).
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Infobox references

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.[4]

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.[4][5]

It is often used to invert secondary alcohols. After converting the alcohol to a good leaving group, such as a mesylate, direct SN2 substitution with the acetate produces the O-acetate with inverted stereochemistry, which can be converted back to a hydroxyl group.[4]

Caesium acetate is occasionally used instead of caesium formate in petroleum drilling fluids.[6]

References

  1. ^ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, Florida: CRC Press. p. B-91. ISBN 0-8493-0462-8..
  2. ^ a b 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. ^ PubChem. "Cesium acetate". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-01-18.
  4. ^ a b c 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
  5. ^ Koepp, E.; Vögtle, F. (1987), "Perkin-Synthese mit Cäsiumacetat", Synthesis, 1987 (2): 177–179, doi:10.1055/s-1987-27880.
  6. ^ "cesium_acetate". glossary.slb.com. Retrieved 2026-01-18.

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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