:Caesium acetate
{{chembox
| verifiedrevid = 409701857
| Name =
| Reference = {{RubberBible62nd|page=B-91}}.
| ImageFile = cesium acetate.svg
| ImageSize = 120px
| ImageCaption = Structural formula
| ImageFile1 = Caesiumacetat.png
| ImageFileL1 = Acetate-anion-3D-balls.png
| ImageFileR1 = Caesium-3D.png
| ImageSize1 = 240px
| ImageCaption1 = Unit cell of anhydrous caesium acetate.
| ImageAlt1 = anhydrous caesium acetate crystallizes in a hexagonal unit cell.
| PIN = Caesium acetate
| OtherNames = Cesium acetate
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 141192
| InChI = 1/C2H4O2.Cs/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1
| InChIKey = ZOAIGCHJWKDIPJ-REWHXWOFAB
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C2H4O2.Cs/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZOAIGCHJWKDIPJ-UHFFFAOYSA-M
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 3396-11-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = M74D2UJ8C9
| PubChem = 160687
| SMILES = [Cs+].[O-]C(=O)C
}}
| Section2 = {{Chembox Properties
| C=2 | H=3 | O=2 | Cs=1
| MolarMass = 191.949 g/mol
| Appearance = colourless, hygroscopic
| Density = 2.423 g/cm3, solid
| MeltingPtC = 194
| BoilingPtC = 945
| Solubility = 945.1 g/100 g (−2.5 °C)
1345.5 g/100 ml (88.5 °C)
}}
| Section3 =
| Section4 = {{Chembox Structure
| CrystalStruct = Primitive hexagonal
| LattConst_a = 1488.0 pm
| LattConst_c = 397.65 pm
| SpaceGroup = P6/m, No. 175
| UnitCellFormulas = 6
| UnitCellVolume = 76.542 cm3·mol−1
}}
| Section5 =
| Section6 =
| Section7 = {{Chembox Hazards
| FlashPt = Non-flammable
}}
| Section8 = {{Chembox Related
| OtherAnions = Caesium formate
| OtherCations = Lithium acetate
Sodium acetate
Potassium acetate
Rubidium 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.{{Citation|last=Yode|first=Ryan|title=Cesium Acetate|date=2015|url=https://onlinelibrary.wiley.com/doi/abs/10.1002/047084289X.rn01845|encyclopedia=Encyclopedia of Reagents for Organic Synthesis|pages=1–11|publisher=John Wiley & Sons|language=en|doi=10.1002/047084289x.rn01845|isbn=978-0-470-84289-8|access-date=2020-07-21}}
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.{{citation|last1=Koepp|first1=E.|title=Perkin-Synthese mit Cäsiumacetat|journal=Synthesis|volume=1987|issue=2|pages=177–179|year=1987|doi=10.1055/s-1987-27880|last2=Vögtle|first2=F.}}.
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.
Caesium acetate is occasionally used instead of caesium formate in petroleum drilling fluids.{{cn|date=October 2013}}
References
{{Reflist}}
Further reading
- {{citation | last1 = Torisawa | first1 = Yasuhiro | last2 = Okabe | first2 = Hiromitsu | last3 = Ikegami | first3 = Shiro | title = Efficient Inversions of Secondary Alcohols using Cesium Acetate and 18-Crown-6 | journal = Chem. Lett. | year = 1984 | volume = 13 | issue = 9 | pages = 1555–56 | doi = 10.1246/cl.1984.1555| doi-access = free }}.
External links
- [https://web.archive.org/web/20080511192739/http://specialmetals.chemetall.com/pdf/Cesium_Acetate_pure.pdf Caesium acetate factsheet from Chemetall GmbH]
{{Caesium compounds}}
{{Acetates}}