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

3396-11-0^Y

3D model (JSmol)

Interactive image

ChemSpider

141192^Y

ECHA InfoCard

100.020.226

PubChem CID

160687

UNII

M74D2UJ8C9^Y

CompTox Dashboard (EPA)

DTXSID00883971

InChI

InChI=1S/C2H4O2.Cs/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1^Y
Key: ZOAIGCHJWKDIPJ-UHFFFAOYSA-M^Y
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

Primitve 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)

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).

Y verify (what is ^YN ?)

Infobox references

Chemical compound

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]

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 S_N2 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.^{[citation needed]}

References

^ 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..
^ ^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.
^ ^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
^ Koepp, E.; Vögtle, F. (1987), "Perkin-Synthese mit Cäsiumacetat", Synthesis, 1987 (2): 177–179, doi:10.1055/s-1987-27880.