Structural formula | |||
Unit cell of anhydrous caesium acetate. | |||
Names | |||
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Preferred IUPAC name Caesium acetate | |||
Other names Cesium acetate | |||
Identifiers | |||
3D model (JSmol) | |||
ChemSpider | |||
ECHA InfoCard | 100.020.226 | ||
PubChem CID | |||
UNII | |||
CompTox Dashboard (EPA) | |||
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Properties | |||
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) | ||
945.1 g/100 g (−2.5 °C) 1345.5 g/100 ml (88.5 °C) | |||
Structure [2] | |||
Primitve hexagonal | |||
P6/m, No. 175 | |||
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). |
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]
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 SN2 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 ]
In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl functional group bound to a saturated carbon atom. The term alcohol originally referred to the primary alcohol ethanol, which is used as a drug and is the main alcohol present in alcoholic drinks. An important class of alcohols, of which methanol and ethanol are the simplest examples, includes all compounds which conform to the general formula CnH2n+1OH. Simple monoalcohols that are the subject of this article include primary, secondary and tertiary alcohols.
Caesium is a chemical element with the symbol Cs and atomic number 55. It is a soft, silvery-golden alkali metal with a melting point of 28.5 °C (83.3 °F), 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. The element has 40 known isotopes, making it, along with barium and mercury, one of the elements with the most isotopes. Caesium-137, a fission product, is extracted from waste produced by nuclear reactors.
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.
In chemistry, an ester is a compound derived from an oxoacid in which at least one hydroxyl group is replaced by an alkoxy group, as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils.
In organic chemistry, a ketene is an organic compound of the form RR'C=C=O, where R and R' are two arbitrary monovalent chemical groups. The name may also refer to the specific compound ethenone H2C=C=O, the simplest ketene.
In organic chemistry, butyl is a four-carbon alkyl radical or substituent group with general chemical formula −C4H9, derived from either of the two isomers of butane.
In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure R−CH2−C6H5. Benzyl features a benzene ring attached to a methylene group group.
Caesium fluoride or cesium fluoride is an inorganic compound with the formula CsF and it is a hygroscopic white salt. Caesium fluoride can be used in organic synthesis as a source of the fluoride anion. Caesium also has the highest electropositivity of all non-radioactive elements and fluorine has the highest electronegativity of all known elements.
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.
Dess–Martin periodinane (DMP) is a chemical reagent used in the Dess–Martin oxidation, oxidizing primary alcohols to aldehydes and secondary alcohols to ketones. This periodinane has several advantages over chromium- and DMSO-based oxidants that include milder conditions, shorter reaction times, higher yields, simplified workups, high chemoselectivity, tolerance of sensitive functional groups, and a long shelf life. However, use on an industrial scale is made difficult by its cost and its potentially explosive nature. It is named after the American chemists Daniel Benjamin Dess and James Cullen Martin who developed the reagent in 1983. It is based on IBX, but due to the acetate groups attached to the central iodine atom, DMP is much more reactive than IBX and is much more soluble in organic solvents.
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.
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.
Propan-1-ol is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colorless liquid and an isomer of 2-propanol. It is formed naturally in small amounts during many fermentation processes and used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.
Caesium carbonate or cesium carbonate is a white crystalline solid compound. Caesium carbonate has a high solubility in polar solvents such as water, alcohol and DMF. Its solubility is higher in organic solvents compared to other carbonates like potassium and sodium carbonates, 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.
The Mukaiyama taxol total synthesis published by the group of Teruaki Mukaiyama of the Tokyo University of Science between 1997 and 1999 was the 6th successful taxol total synthesis. The total synthesis of Taxol is considered a hallmark in organic synthesis.
3,4-Dihydropyran (DHP) is a heterocyclic compound with the formula C5H8O. The six-membered C5O ring has the unsaturation adjacent to oxygen. The isomeric 3,6-dihydropyran has a methylene separating the double bond and oxygen. DHP is used for protecting group for alcohols. It is a colorless liquid.
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.
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.
Trifluoroacetone (1,1,1-trifluoroacetone) is an organofluorine compound with the chemical formula CF3C(O)CH3. The compound is a colorless liquid with chloroform-like odour.