Caesium acetate

Caesium acetate^[1]
	; Structural formula
	; Unit cell of anhydrous caesium acetate.
Names
	Preferred IUPAC name Caesium acetate
	Other names Cesium acetate
Identifiers
CAS Number	3396-11-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	141192 ;
ECHA InfoCard	100.020.226
PubChem CID	160687;
UNII	M74D2UJ8C9 ;
CompTox Dashboard (EPA)	DTXSID00883971 ;
	InChI InChI=1S/C2H4O2.Cs/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1 Key: ZOAIGCHJWKDIPJ-UHFFFAOYSA-M ; 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
Crystal structure	Primitive hexagonal
Space group	P6/m, No. 175
Lattice constant	a = 1488.0 pm, c = 397.65 pm
Lattice volume (V)	76.542 cm3·mol−1
Formula units (Z)	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). verify (what is ?) 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.^[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. After converting the alcohol to a good leaving group, such as a mesylate, direct S_N2 substitution with the acetate produces the O-acetate with inverted stereochemistry, which can be 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.

External links

Caesium acetate factsheet from Chemetall GmbH

[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..

[crystal_structure-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.

[e-EROS-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.

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Uses

References

Further reading

External links