Caesium acetate

Caesium acetate or cesium acetate is an ionic caesium compound with the molecular formula CH₃CO₂Cs. 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
Unit cell of anhydrous caesium acetate.
Names
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
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/cm^3, 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 cm^3·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).
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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 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.

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.

External links

• Caesium acetate factsheet from Chemetall GmbH

Acetyl halides and salts of the acetate ion
AcOH																	He
LiOAc	Be(OAc)2 BeAcOH											B(OAc)3	AcOAc ROAc	NH4OAc	AcOOH	FAc	Ne
NaOAc	Mg(OAc)2											Al(OAc)3 ALSOL Al(OAc)2OH Al2SO4(OAc)4	Si	P	S	ClAc	Ar
KOAc	Ca(OAc)2	Sc(OAc)3	Ti(OAc)4	VO(OAc)3	Cr(OAc)2 Cr(OAc)3	Mn(OAc)2 Mn(OAc)3	Fe(OAc)2 Fe(OAc)3	Co(OAc)2, Co(OAc)3	Ni(OAc)2	Cu(OAc)2	Zn(OAc)2	Ga(OAc)3	Ge	As(OAc)3	Se	BrAc	Kr
RbOAc	Sr(OAc)2	Y(OAc)3	Zr(OAc)4	Nb	Mo(OAc)2	Tc	Ru(OAc)2 Ru(OAc)3 Ru(OAc)4	Rh2(OAc)4	Pd(OAc)2	AgOAc	Cd(OAc)2	In	Sn(OAc)2 Sn(OAc)4	Sb(OAc)3	Te	IAc	Xe
CsOAc	Ba(OAc)2		Hf	Ta	W	Re	Os	Ir	Pt(OAc)2	Au	Hg2(OAc)2, Hg(OAc)2	TlOAc Tl(OAc)3	Pb(OAc)2 Pb(OAc)4	Bi(OAc)3	Po	At	Rn
Fr	Ra		Rf	Db	Sg	Bh	Hs	Mt	Ds	Rg	Cn	Nh	Fl	Mc	Lv	Ts	Og
		↓
		La(OAc)3	Ce(OAc)x	Pr	Nd	Pm	Sm(OAc)3	Eu(OAc)3	Gd(OAc)3	Tb	Dy(OAc)3	Ho(OAc)3	Er	Tm	Yb(OAc)3	Lu(OAc)3
		Ac	Th	Pa	UO2(OAc)2	Np	Pu	Am	Cm	Bk	Cf	Es	Fm	Md	No	Lr