Tin(IV) chloride

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Tin(IV) chloride
Tin (IV) chloride Tin(IV) chloride.jpg
Tin (IV) chloride
Anhydrous Tin(IV) chloride
Tin(IV) chloride pentahydrate.jpg Tin(IV) chloride pentahydrate.jpg
Tin(IV) chloride pentahydrate.jpg
Tin(IV) chloride pentahydrate
Tin(IV)-chlorid.svg
SnCl4 OH2 2.svg
Names
IUPAC names
Tetrachlorostannane
Tin tetrachloride
Tin(IV) chloride
Other names
Stannic chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.028.717 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 231-588-9
PubChem CID
RTECS number
  • XP8750000
UNII
UN number 1827
  • InChI=1S/4ClH.Sn/h4*1H;/q;;;;+4/p-4 Yes check.svgY
    Key: HPGGPRDJHPYFRM-UHFFFAOYSA-J Yes check.svgY
  • InChI=1/4ClH.Sn/h4*1H;/q;;;;+4/p-4
    Key: HPGGPRDJHPYFRM-XBHQNQODAC
  • Cl[Sn](Cl)(Cl)Cl
Properties
SnCl4
Molar mass 260.50 g/mol (anhydrous)
350.60 g/mol (pentahydrate)
AppearanceColorless fuming liquid
Odor Acrid
Density 2.226 g/cm3 (anhydrous)
2.04 g/cm3 (pentahydrate)
Melting point −34.07 °C (−29.33 °F; 239.08 K) (anhydrous)
56 °C (133 °F; 329 K) (pentahydrate)
Boiling point 114.15 °C (237.47 °F; 387.30 K)
hydrolysis,very hygroscopic (anhydrous)
very soluble (pentahydrate)
Solubility soluble in alcohol, benzene, toluene, chloroform, acetone, kerosene, CCl4, methanol, gasoline, CS2
Vapor pressure 2.4 kPa
115·10−6 cm3/mol
1.512
Structure
monoclinic (P21/c)
Hazards
GHS labelling:
GHS-pictogram-acid.svg
Danger
H314, H412
P260, P264, P273, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
NFPA 704 (fire diamond)
3
0
1
Safety data sheet (SDS) ICSC 0953
Related compounds
Other anions
Tin(IV) fluoride
Tin(IV) bromide
Tin(IV) iodide
Other cations
Carbon tetrachloride
Silicon tetrachloride
Germanium tetrachloride
Lead(IV) chloride
Related compounds
Tin(II) chloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tin(IV) chloride, also known as tin tetrachloride or stannic chloride, is an inorganic compound with the formula Sn Cl 4. It is a colorless hygroscopic liquid, which fumes on contact with air. It is used as a precursor to other tin compounds. [1] It was first discovered by Andreas Libavius (1550–1616) and was known as spiritus fumans libavii.

Contents

Preparation

It is prepared from reaction of chlorine gas with tin at 115 °C (239 °F).

Sn + 2 Cl2 → SnCl4

Structure

Anhydrous tin(IV) chloride solidifies at −33 °C to give monoclinic crystals with the P21/c space group. It is isostructural with SnBr4. The molecules adopt near-perfect tetrahedral symmetry with average Sn–Cl distances of 227.9(3) pm. [2]

Structure of solid SnCl4. SnCl4-xtal-down-b-axis-2005-CM-3D-polyhedra.png
Structure of solid SnCl4.

Reactions

Tin(IV) chloride is well known as a Lewis acid. Thus it forms hydrates. The pentahydrate SnCl4·5H2O was formerly known as butter of tin. They all consist of [SnCl4(H2O)2] molecules together with varying amounts of water of crystallization. The additional water molecules link together the molecules of [SnCl4(H2O)2] through hydrogen bonds. [3] Although the pentahydrate is the most common hydrate, lower hydrates have also been characterised. [4]

Aside from water, other Lewis bases form adducts with SnCl4. These include ammonia and organophosphines. The complex [SnCl6]2− is formed with hydrochloric acid making hexachlorostannic acid. [1]

Applications

Precursor to organotin compounds

Anhydrous tin(IV) chloride is a major precursor in organotin chemistry. Upon treatment with Grignard reagents, tin(IV) chloride gives tetraalkyltin compounds: [5]

SnCl4 + 4 RMgCl → SnR4 + 4 MgCl2

Anhydrous tin(IV) chloride reacts with tetraorganotin compounds in redistribution reactions:

SnCl4 + SnR4 → 2 SnCl2R2

These organotin halides are useful precursors to catalysts (e.g., dibutyltin dilaurate) and polymer stabilizers. [6]

Organic synthesis

SnCl4 is used in Friedel-Crafts reactions as a Lewis acid catalyst. [1] For example, the acetylation of thiophene to give 2-acetylthiophene is promoted by tin(IV) chloride. [7] Similarly, tin(IV) chloride is useful for the nitrations. [8]

Safety

Stannic chloride was used as a chemical weapon in World War I, as it formed an irritating (but non-deadly) dense smoke on contact with air: it was substituted for by a mixture of silicon tetrachloride and titanium tetrachloride near the end of the war due to shortages of tin. [9]

Related Research Articles

<span class="mw-page-title-main">Tin</span> Chemical element, symbol Sn and atomic number 50

Tin is a chemical element with the symbol Sn and atomic number 50. Tin is a silvery-coloured metal.

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

Zinc chloride is the name of inorganic chemical compounds with the formula ZnCl2 and its hydrates. Zinc chlorides, of which nine crystalline forms are known, are colorless or white, and are highly soluble in water. This salt is hygroscopic and even deliquescent. Zinc chloride finds wide application in textile processing, metallurgical fluxes, and chemical synthesis. No mineral with this chemical composition is known aside from the very rare mineral simonkolleite, Zn5(OH)8Cl2·H2O.

<span class="mw-page-title-main">Titanium tetrachloride</span> Inorganic chemical compound

Titanium tetrachloride is the inorganic compound with the formula TiCl4. It is an important intermediate in the production of titanium metal and the pigment titanium dioxide. TiCl4 is a volatile liquid. Upon contact with humid air, it forms thick clouds of titanium dioxide and hydrochloric acid, a reaction that was formerly exploited for use in smoke machines. It is sometimes referred to as "tickle" or "tickle 4" due to the phonetic resemblance of its molecular formula to the word.

In chemistry, water(s) of crystallization or water(s) of hydration are water molecules that are present inside crystals. Water is often incorporated in the formation of crystals from aqueous solutions. In some contexts, water of crystallization is the total mass of water in a substance at a given temperature and is mostly present in a definite (stoichiometric) ratio. Classically, "water of crystallization" refers to water that is found in the crystalline framework of a metal complex or a salt, which is not directly bonded to the metal cation.

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

Lithium chloride is a chemical compound with the formula LiCl. The salt is a typical ionic compound (with certain covalent characteristics), although the small size of the Li+ ion gives rise to properties not seen for other alkali metal chlorides, such as extraordinary solubility in polar solvents (83.05 g/100 mL of water at 20 °C) and its hygroscopic properties.

In chemistry the term stannate refers to compounds of tin (Sn). Stannic acid (Sn(OH)4), the formal precursor to stannates, does not exist and is actually a hydrate of SnO2. The term is also used in naming conventions as a suffix; for example the hexachlorostannate ion is SnCl2−
6
.

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

Chromium(III) chloride (also called chromic chloride) describes any of several chemical compounds with the formula CrCl3 · xH2O, where x can be 0, 5, and 6. The anhydrous compound with the formula CrCl3 is a violet solid. The most common form of the trichloride is the dark green hexahydrate, CrCl3 · 6 H2O. Chromium chlorides find use as catalysts and as precursors to dyes for wool.

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

Nickel(II) chloride (or just nickel chloride) is the chemical compound NiCl2. The anhydrous salt is yellow, but the more familiar hydrate NiCl2·6H2O is green. Nickel(II) chloride, in various forms, is the most important source of nickel for chemical synthesis. The nickel chlorides are deliquescent, absorbing moisture from the air to form a solution. Nickel salts have been shown to be carcinogenic to the lungs and nasal passages in cases of long-term inhalation exposure.

<span class="mw-page-title-main">Organotin chemistry</span> Branch of organic chemistry

Organotin compounds or stannanes are chemical compounds based on tin with hydrocarbon substituents. Organotin chemistry is part of the wider field of organometallic chemistry. The first organotin compound was diethyltin diiodide, discovered by Edward Frankland in 1849. The area grew rapidly in the 1900s, especially after the discovery of the Grignard reagents, which are useful for producing Sn–C bonds. The area remains rich with many applications in industry and continuing activity in the research laboratory.

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

Tin(II) chloride, also known as stannous chloride, is a white crystalline solid with the formula SnCl2. It forms a stable dihydrate, but aqueous solutions tend to undergo hydrolysis, particularly if hot. SnCl2 is widely used as a reducing agent (in acid solution), and in electrolytic baths for tin-plating. Tin(II) chloride should not be confused with the other chloride of tin; tin(IV) chloride or stannic chloride (SnCl4).

<span class="mw-page-title-main">Tin(IV) oxide</span> Chemical compound known as stannic oxide, cassiterite and tin ore

Tin(IV) oxide, also known as stannic oxide, is the inorganic compound with the formula SnO2. The mineral form of SnO2 is called cassiterite, and this is the main ore of tin. With many other names, this oxide of tin is an important material in tin chemistry. It is a colourless, diamagnetic, amphoteric solid.

Tin(IV) iodide, also known as stannic iodide, is the chemical compound with the formula SnI4. This tetrahedral molecule crystallizes as a bright orange solid that dissolves readily in nonpolar solvents such as benzene.

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

Trimethyltin chloride is an organotin compound with the formula (CH3)3SnCl. It is a white solid that is highly toxic and malodorous. It is susceptible to hydrolysis.

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

Tetramethyltin is an organometallic compound with the formula (CH3)4Sn. This liquid, one of the simplest organotin compounds, is useful for transition-metal mediated conversion of acid chlorides to methyl ketones and aryl halides to aryl methyl ketones. It is volatile and toxic, so care should be taken when using it in the laboratory.

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

Tin(IV) fluoride is a chemical compound of tin and fluorine with the chemical formula SnF4 and is a white solid with a melting point above 700 °C.

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

Titanium nitrate is the inorganic compound with formula Ti(NO3)4. It is a colorless, diamagnetic solid that sublimes readily. It is an unusual example of a volatile binary transition metal nitrate. Ill defined species called titanium nitrate are produced upon dissolution of titanium or its oxides in nitric acid.

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

Tributyltin chloride is an organotin compound with the formula (C4H9)3SnCl. It is a colorless liquid that is soluble in organic solvents.

<span class="mw-page-title-main">Transition metal ether complex</span>

In chemistry, a transition metal ether complex is a coordination complex consisting of a transition metal bonded to one or more ether ligand. The inventory of complexes is extensive. Common ether ligands are diethyl ether and tetrahydrofuran. Common chelating ether ligands include the glymes, dimethoxyethane (dme) and diglyme, and the crown ethers. Being lipophilic, metal-ether complexes often exhibit solubility in organic solvents, a property of interest in synthetic chemistry.

Cobalt compounds are chemical compounds formed by cobalt with other elements. In the compound, the most stable oxidation state of cobalt is the +2 oxidation state, and in the presence of specific ligands, there are also stable compounds with +3 valence. In addition, there are cobalt compounds in high oxidation states +4, +5 and low oxidation states -1, 0, +1.

References

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  2. Reuter, Hans; Pawlak, Rüdiger (April 2000). "Die Molekül- und Kristallstruktur von Zinn(IV)-chlorid". Zeitschrift für anorganische und allgemeine Chemie (in German). 626 (4): 925–929. doi:10.1002/(SICI)1521-3749(200004)626:4<925::AID-ZAAC925>3.0.CO;2-R.
  3. Barnes, John C.; Sampson, Hazel A.; Weakley, Timothy J. R. (1980). "Structures of di-μ-hydroxobis[aquatrichlorotin(IV)]-1,4-dioxane(1/3), di-μ-hydroxobis[aquatrichlorotin(IV)]-1,8-epoxy-p-menthane(1/4), di-m-hydroxobis[aquatribromotin(IV)]-1,8-epoxy-p-menthane(1/4), di-μ-hydroxobis[aquatrichlorotin(IV)], and cis-diaquatetrachlorotin(IV)". J. Chem. Soc., Dalton Trans. (6): 949. doi:10.1039/DT9800000949.
  4. Genge, Anthony R. J.; Levason, William; Patel, Rina; et al. (2004). "Hydrates of tin tetrachloride". Acta Crystallographica Section C. 60 (4): i47–i49. doi: 10.1107/S0108270104005633 . PMID   15071197.
  5. Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN   978-0-08-037941-8.
  6. G. G. Graf "Tin, Tin Alloys, and Tin Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2005 Wiley-VCH, Weinheim. doi : 10.1002/14356007.a27_049
  7. John R. Johnson, G. E. May (1938). "2-Acetothienone". Organic Syntheses. 18: 1. doi:10.15227/orgsyn.018.0001.
  8. Thurston, David E.; Murty, Varanasi S.; Langley, David R.; Jones, Gary B. (1990). "O-Debenzylation of a Pyrrolo[2,1-c][1,4]benzodiazepine in the Presence of a Carbinolamine Functionality: Synthesis of DC-81". Synthesis . 1990: 81–84. doi:10.1055/s-1990-26795.
  9. Fries, Amos A. (2008). Chemical Warfare. Read. pp. 148–49, 407. ISBN   978-1-4437-3840-8..