Caesium acetate

Last updated
Caesium acetate [1]
Cesium acetate.svg
Structural formula
Caesiumacetat.png
Unit cell of anhydrous caesium acetate.
Acetate-anion-3D-balls.png
Caesium-3D.png
Names
Preferred IUPAC name
Caesium acetate
Other names
Cesium acetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.020.226 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C2H4O2.Cs/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1 Yes check.svgY
    Key: ZOAIGCHJWKDIPJ-UHFFFAOYSA-M Yes check.svgY
  • InChI=1/C2H4O2.Cs/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1
    Key: ZOAIGCHJWKDIPJ-REWHXWOFAB
  • [Cs+].[O-]C(=O)C
Properties
C2H3CsO2
Molar mass 191.949 g/mol
Appearancecolourless, 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)
945.1 g/100 g (−2.5 °C)
1345.5 g/100 ml (88.5 °C)
Structure [2]
Primitve hexagonal
P6/m, No. 175
a = 1488.0 pm, c = 397.65 pm [2]
76.542 cm3·mol−1
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

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 SN2 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 ]

Related Research Articles

<span class="mw-page-title-main">Caesium</span> Chemical element with atomic number 55 (Cs)

Caesium is a chemical element; it has symbol Cs and atomic number 55. It is a soft, silvery-golden alkali metal with a melting point of 28.5 °C, which makes it one of only five elemental metals that are liquid at or near room temperature. Caesium has physical and chemical properties similar to those of rubidium and potassium. It is pyrophoric and reacts with water even at −116 °C (−177 °F). It is the least electronegative element, with a value of 0.79 on the Pauling scale. It has only one stable isotope, caesium-133. Caesium is mined mostly from pollucite. Caesium-137, a fission product, is extracted from waste produced by nuclear reactors. It has the largest atomic radius of all elements whose radii have been measured or calculated, at about 260 picometers.

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a functional group derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

Transesterification is the process of exchanging the organic functional group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. Strong acids catalyze the reaction by donating a proton to the carbonyl group, thus making it a more potent electrophile. Bases catalyze the reaction by removing a proton from the alcohol, thus making it more nucleophilic. The reaction can also be accomplished with the help of enzymes, particularly lipases.

<span class="mw-page-title-main">Alkylation</span> Transfer of an alkyl group from one molecule to another

Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene. Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents.

<span class="mw-page-title-main">1-Pentanol</span> Chemical compound

1-Pentanol,, is an organic compound with the formula CH3CH2CH2CH2CH2OH and is classified as a primary alcohol. It is a colourless liquid with a distinctive aroma. It is one of 8 isomeric alcohols with the formula C5H11OH. It is used as a solvent, a biological drying agent and in the synthesis of some fragrance compounds. It is also a common component of fusel alcohols, the undesirable byproducts of alcoholic fermentation.

<span class="mw-page-title-main">Caesium fluoride</span> Chemical compound

Caesium fluoride is an inorganic compound with the formula CsF. A hygroscopic white salt, caesium fluoride is used in the synthesis of organic compounds as a source of the fluoride anion. The compound is noteworthy from the pedagogical perspective as caesium also has the highest electropositivity of all commonly available elements and fluorine has the highest electronegativity.

The Perkin reaction is an organic reaction developed by English chemist William Henry Perkin that is used to make cinnamic acids. It gives an α,β-unsaturated aromatic acid or α-substituted β-aryl acrylic acid by the aldol condensation of an aromatic aldehyde and an acid anhydride, in the presence of an alkali salt of the acid. The alkali salt acts as a base catalyst, and other bases can be used instead.

<i>N</i>,<i>N</i>-Dicyclohexylcarbodiimide Chemical compound

N,N′-Dicyclohexylcarbodiimide (DCC or DCCD) is an organic compound with the chemical formula (C6H11N)2C. It is a waxy white solid with a sweet odor. Its primary use is to couple amino acids during artificial peptide synthesis. The low melting point of this material allows it to be melted for easy handling. It is highly soluble in dichloromethane, tetrahydrofuran, acetonitrile and dimethylformamide, but insoluble in water.

<span class="mw-page-title-main">Caesium chloride</span> Chemical compound

Caesium chloride or cesium chloride is the inorganic compound with the formula CsCl. This colorless salt is an important source of caesium ions in a variety of niche applications. Its crystal structure forms a major structural type where each caesium ion is coordinated by 8 chloride ions. Caesium chloride dissolves in water. CsCl changes to NaCl structure on heating. Caesium chloride occurs naturally as impurities in carnallite, sylvite and kainite. Less than 20 tonnes of CsCl is produced annually worldwide, mostly from a caesium-bearing mineral pollucite.

<span class="mw-page-title-main">Palladium(II) acetate</span> Chemical compound

Palladium(II) acetate is a chemical compound of palladium described by the formula [Pd(O2CCH3)2]n, abbreviated [Pd(OAc)2]n. It is more reactive than the analogous platinum compound. Depending on the value of n, the compound is soluble in many organic solvents and is commonly used as a catalyst for organic reactions.

<span class="mw-page-title-main">Allyl alcohol</span> Organic compound (CH2=CHCH2OH)

Allyl alcohol is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a precursor to many specialized compounds such as flame-resistant materials, drying oils, and plasticizers. Allyl alcohol is the smallest representative of the allylic alcohols.

2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group.

<span class="mw-page-title-main">1-Propanol</span> Primary alcohol compound

1-Propanol is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colourless liquid and an isomer of 2-propanol. 1-Propanol is used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.

<span class="mw-page-title-main">Silver acetate</span> Chemical compound with formula AgC₂H₃O₂

Silver acetate is a coordination compound with the empirical formula CH3CO2Ag (or AgC2H3O2). A photosensitive, white, crystalline solid, it is a useful reagent in the laboratory as a source of silver ions lacking an oxidizing anion.

<span class="mw-page-title-main">Caesium carbonate</span> Chemical compound

Caesium carbonate or cesium carbonate is a chemical compound with the chemical formula Cs2CO3. It is white crystalline solid. Caesium carbonate has a high solubility in polar solvents such as water, ethanol and DMF. Its solubility is higher in organic solvents compared to other carbonates like potassium carbonate and sodium carbonate, although it remains quite insoluble in other organic solvents such as toluene, p-xylene, and chlorobenzene. This compound is used in organic synthesis as a base. It also appears to have applications in energy conversion.

<span class="mw-page-title-main">Lead(IV) acetate</span> Organometallic compound (Pb(C2H3O2)4)

Lead(IV) acetate or lead tetraacetate is an metalorganic compound with chemical formula Pb(C2H3O2)4. It is a colorless solid that is soluble in nonpolar, organic solvents, indicating that it is not a salt. It is degraded by moisture and is typically stored with additional acetic acid. The compound is used in organic synthesis.

<span class="mw-page-title-main">Erlenmeyer–Plöchl azlactone and amino-acid synthesis</span>

The Erlenmeyer–Plöchl azlactone and amino acid synthesis, named after Friedrich Gustav Carl Emil Erlenmeyer who partly discovered the reaction, is a series of chemical reactions which transform an N-acyl glycine to various other amino acids via an oxazolone.

The Ritter reaction is a chemical reaction that transforms a nitrile into an N-alkyl amide using various electrophilic alkylating reagents. The original reaction formed the alkylating agent using an alkene in the presence of a strong acid.

<span class="mw-page-title-main">Trichloroacetonitrile</span> Chemical compound

Trichloroacetonitrile is an organic compound with the formula CCl3CN. It is a colourless liquid, although commercial samples often are brownish. It is used commercially as a precursor to the fungicide etridiazole. It is prepared by dehydration of trichloroacetamide. As a bifunctional compound, trichloroacetonitrile can react at both the trichloromethyl and the nitrile group. The electron-withdrawing effect of the trichloromethyl group activates the nitrile group for nucleophilic additions. The high reactivity makes trichloroacetonitrile a versatile reagent, but also causes its susceptibility towards hydrolysis.

In organic chemistry, alkynylation is an addition reaction in which a terminal alkyne is added to a carbonyl group to form an α-alkynyl alcohol.

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. 1 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. 1 2 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