Tin(IV) acetate

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Tin(IV) acetate
4.svg Acetat-Ion.svg Sn4+.svg
Names
Other names
Tin(IV) acetate
Tin tetraacetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.157.007 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 628-765-1
PubChem CID
  • InChI=1S/4C2H4O2.Sn/c4*1-2(3)4;/h4*1H3,(H,3,4);/q;;;;+4/p-4
    Key: YJGJRYWNNHUESM-UHFFFAOYSA-J
  • CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].[Sn+4]
Properties
Sn(CH3COO)4
Molar mass 353.89
Appearancewhite needles [1]
Melting point 242 °C (468 °F; 515 K)
Hazards
GHS labelling: [2]
GHS-pictogram-exclam.svg
Warning
H302, H312, H332
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P501
Related compounds
Other anions
Tin(IV) fluoroacetate
Other cations
Lead(IV) acetate
Related compounds
Tin(II) acetate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tin(IV) acetate is the acetate salt of tin(IV), with the chemical formula of Sn(CH3COO)4.

Contents

Preparation

Tin(IV) acetate can be refluxed by thallium acetate and tin(IV) iodide in acetic anhydride. After the reaction is completed, the solution is concentrated and cooled to precipitate crystals, which are washed with anhydrous ether and dried in vacuum: [1]

4 CH3COOTl + SnI4 → Sn(CH3COO)4 + 4 TlI↓

Tetraphenyltin is refluxed at 120°C in acetic acid-acetic anhydride mixture, and tin(IV) acetate can be quantitatively generated: [3]

4 CH3COOH + (C6H5)4Sn → Sn(CH3COO)4 + 4C6H6

The reaction of tin(IV) nitrate with acetic acid and acetic anhydride can also produce tin(IV) acetate, but the reaction with trifluoroacetic anhydride can not get its analogue, but (NO2)2[Sn(CF3COO)6]. [4]

4 CH3COOH + Sn(NO3)4 → Sn(CH3COO)4 + 4 HNO3

Properties

Tin(IV) acetate decomposes in water to form tin hydroxide and acetic acid: [1]

Sn(CH3COO)4 + 4 H2O → Sn(OH)4 + 4 CH3COOH

It reacts with sulfur-containing species such as thiols to generate corresponding sulfur-containing tin compounds. [5]

Related Research Articles

In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively charged sodium ions and negatively charged chloride ions.

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

Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis. It is a colorless solid. Related compounds are dichloroacetic acid and trichloroacetic acid.

<span class="mw-page-title-main">Fischer–Speier esterification</span>

Fischer esterification or Fischer–Speier esterification is a special type of esterification by refluxing a carboxylic acid and an alcohol in the presence of an acid catalyst. The reaction was first described by Emil Fischer and Arthur Speier in 1895. Most carboxylic acids are suitable for the reaction, but the alcohol should generally be primary or secondary. Tertiary alcohols are prone to elimination. Contrary to common misconception found in organic chemistry textbooks, phenols can also be esterified to give good to near quantitative yield of products. Commonly used catalysts for a Fischer esterification include sulfuric acid, p-toluenesulfonic acid, and Lewis acids such as scandium(III) triflate. For more valuable or sensitive substrates other, milder procedures such as Steglich esterification are used. The reaction is often carried out without a solvent or in a non-polar solvent to facilitate the Dean-Stark method. Typical reaction times vary from 1–10 hours at temperatures of 60-110 °C.

In organic chemistry, an acyl chloride is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.

<span class="mw-page-title-main">Acetic anhydride</span> Organic compound with formula (CH₃CO)₂O

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.

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

Sodium acetate, CH3COONa, also abbreviated NaOAc, is the sodium salt of acetic acid. This colorless deliquescent salt has a wide range of uses.

<span class="mw-page-title-main">Acetyl chloride</span> Organic compound (CH₃COCl)

Acetyl chloride is an acyl chloride derived from acetic acid. It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl.

<span class="mw-page-title-main">Organic acid anhydride</span> Any chemical compound having two acyl groups bonded to the same oxygen atom

An organic acid anhydride is an acid anhydride that is an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhydride, where the parent acid is a carboxylic acid, the formula of the anhydride being (RC(O))2O. Symmetrical acid anhydrides of this type are named by replacing the word acid in the name of the parent carboxylic acid by the word anhydride. Thus, (CH3CO)2O is called acetic anhydride.Mixed (or unsymmetrical) acid anhydrides, such as acetic formic anhydride (see below), are known, whereby reaction occurs between two different carboxylic acids. Nomenclature of unsymmetrical acid anhydrides list the names of both of the reacted carboxylic acids before the word "anhydride" (for example, the dehydration reaction between benzoic acid and propanoic acid would yield "benzoic propanoic anhydride").

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

Zinc acetate is a salt with the formula Zn(CH3CO2)2, which commonly occurs as the dihydrate Zn(CH3CO2)2·2H2O. Both the hydrate and the anhydrous forms are colorless solids that are used as dietary supplements. When used as a food additive, it has the E number E650.

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

Lead(IV) acetate or lead tetraacetate is an organometallic 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">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water and other trace elements.

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

Platinum(II) acetate is a purple-colored coordination complex. The complex adopts an unusual structure consisting of a square array of Pt atoms.

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

Anhydrous magnesium acetate has the chemical formula Mg(C2H3O2)2 and in its hydrated form, magnesium acetate tetrahydrate, it has the chemical formula Mg(CH3COO)2 • 4H2O. In this compound magnesium has an oxidation state of 2+. Magnesium acetate is the magnesium salt of acetic acid. It is deliquescent and upon heating, it decomposes to form magnesium oxide. Magnesium acetate is commonly used as a source of magnesium in biological reactions.

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

Barium acetate (Ba(C2H3O2)2) is the salt of barium(II) and acetic acid. Barium acetate is toxic to humans, but has use in chemistry and manufacturing.

<span class="mw-page-title-main">Chloro(pyridine)cobaloxime</span> Chemical compound

Chloro(pyridine)cobaloxime is a coordination compound containing a CoIII center with octahedral coordination. It has been considered as a model compound of vitamin B12 for studying the properties and mechanism of action of the vitamin. It belongs to a class of bis(dimethylglyoximato)cobalt(III) complexes with different axial ligands, called cobaloximes. Chloro(pyridine)cobaloxime is a yellow-brown powder that is sparingly soluble in most solvents, including water.

<span class="mw-page-title-main">Terbium(III) nitrate</span> Chemical compound

Terbium(III) nitrate is an inorganic chemical compound, a salt of terbium and nitric acid, with the formula Tb(NO3)3. The hexahydrate crystallizes as triclinic colorless crystals with the formula [Tb(NO3)3(H2O)4]·2H2O. It can be used to synthesize materials with green emission.

<span class="mw-page-title-main">Tin(IV) nitrate</span> Chemical compound

Tin(IV) nitrate is a salt of tin with nitric acid. It is a volatile white solid, subliming at 40 °C under a vacuum. Unlike other nitrates, it reacts with water to produce nitrogen dioxide.

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

Gallium acetate is a salt composed of a gallium atom trication and three acetate groups as anions where gallium exhibits the +3 oxidation state. It has a chemical formula of Ga(CH3COO)3 although it can be informally referred to as GaAc because Ac is an informal symbol for acetate. Gallium is moderately water-soluble and decomposes to gallium oxide when heated to around 70 °C. Gallium acetate, like other acetate compounds, is a good precursor to ultra-pure compounds, catalysts and nanoscale materials. Gallium acetate is being considered as a substitute in de-icing compounds like calcium chloride and magnesium chloride.

<span class="mw-page-title-main">Holmium acetate</span> Compound of holmium

Holmium acetate is the acetate salt of holmium, with a chemical formula of Ho(CH3COO)3.

Tin(II) acetate is the acetate salt of tin(II), with the chemical formula of Sn(CH3COO)2. It was first discovered in 1822.

References

  1. 1 2 3 Tin(IV) acetate
  2. "Tin(IV) acetate". pubchem.ncbi.nlm.nih.gov.
  3. Sawyer, Albert K.; Frey, Craig (January 1983). "A Simple Synthesis of Tin(IV) Acetate from Tetraphenyltin". Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry. 13 (2): 259–262. doi:10.1080/00945718308059330. ISSN   0094-5714.
  4. Harrison, Philip G.; Khalil, Mutassim I.; Logan, Norman (January 1978). "A contribution to the chemistry of tin(IV) nitrate". Inorganica Chimica Acta. 30: 165–170. doi:10.1016/S0020-1693(00)89031-3.
  5. Mehrotra, R.C.; Srivastava, G.; Vasanta, E.N. (January 1981). "Reactions of tin tetraacetate with sulphur ligands". Inorganica Chimica Acta. 47: 125–130. doi:10.1016/S0020-1693(00)89317-2.

See also

Further reading