Tin(IV) chloride, also known as tin tetrachloride or stannic chloride, is an inorganic compound with the formula SnCl4. It is a colorless hygroscopicliquid, 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.
It is prepared from reaction of chlorine gas with tin at 115 °C (239 °F).
Sn + 2Cl 2 → SnCl 4
StructureEdit
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.
ReactionsEdit
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]
ApplicationsEdit
Precursor to organotin compoundsEdit
Anhydrous tin(IV) chloride is a major precursor in organotin chemistry. Upon treatment with Grignard reagents, tin(IV) chloride gives tetraalkyltin compounds:[5]
These organotin halides are useful precursors to catalysts (e.g., dibutyltin dilaurate) and polymer stabilizers.[6]
Organic synthesisEdit
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]
^ abcEgon Wiberg, Nils Wiberg, Arnold Frederick Holleman (2001). Inorganic Chemistry. Elsevier. ISBN0-12-352651-5.{{cite book}}: CS1 maint: multiple names: authors list (link)
^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.
^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.
^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.
^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
^John R. Johnson, G. E. May (1938). "2-Acetothienone". Organic Syntheses. 18: 1. doi:10.15227/orgsyn.018.0001.
^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.
^Fries, Amos A. (2008). Chemical Warfare. Read. pp. 148–49, 407. ISBN978-1-4437-3840-8..
External linksEdit
Wikimedia Commons has media related to Tin(IV) chloride.
International Chemical Safety Card 0953
at the Wayback Machine (archived 2005-02-28)
October 18, 2023
chloride, also, known, tetrachloride, stannic, chloride, inorganic, compound, with, formula, sncl4, colorless, hygroscopic, liquid, which, fumes, contact, with, used, precursor, other, compounds, first, discovered, andreas, libavius, 1550, 1616, known, spiritu. Tin IV chloride also known as tin tetrachloride or stannic chloride is an inorganic compound with the formula SnCl4 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 Tin IV chloride Tin IV chlorideAnhydrous Tin IV chloride Tin IV chloride pentahydrate jpgTin IV chloride pentahydrateNamesIUPAC names TetrachlorostannaneTin tetrachlorideTin IV chlorideOther names Stannic chlorideIdentifiersCAS Number 7646 78 8 Y10026 06 9 pentahydrate N3D model JSmol Interactive imageChemSpider 22707 YECHA InfoCard 100 028 717EC Number 231 588 9PubChem CID 24287RTECS number XP8750000UNII 67H76LFL3V YUN number 1827CompTox Dashboard EPA DTXSID1029679InChI InChI 1S 4ClH Sn h4 1H q 4 p 4 YKey HPGGPRDJHPYFRM UHFFFAOYSA J YInChI 1 4ClH Sn h4 1H q 4 p 4Key HPGGPRDJHPYFRM XBHQNQODACSMILES Cl Sn Cl Cl ClPropertiesChemical formula SnCl4Molar mass 260 50 g mol anhydrous 350 60 g mol pentahydrate Appearance Colorless fuming liquidOdor AcridDensity 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 Solubility in water hydrolysis very hygroscopic anhydrous very soluble pentahydrate Solubility soluble in alcohol benzene toluene chloroform acetone kerosene CCl4 methanol gasoline CS2Vapor pressure 2 4 kPaMagnetic susceptibility x 115 10 6 cm3 molRefractive index nD 1 512StructureCrystal structure monoclinic P21 c HazardsGHS labelling PictogramsSignal word DangerHazard statements H314 H412Precautionary statements P260 P264 P273 P280 P301 P330 P331 P303 P361 P353 P304 P340 P305 P351 P338 P310 P321 P363 P405 P501NFPA 704 fire diamond 301Safety data sheet SDS ICSC 0953Related compoundsOther anions Tin IV fluorideTin IV bromideTin IV iodideOther cations Carbon tetrachlorideSilicon tetrachlorideGermanium tetrachlorideLead IV chlorideRelated compounds Tin II chlorideExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Preparation 2 Structure 3 Reactions 4 Applications 4 1 Precursor to organotin compounds 4 2 Organic synthesis 5 Safety 6 References 7 External linksPreparation EditIt is prepared from reaction of chlorine gas with tin at 115 C 239 F Sn 2Cl2 SnCl4Structure EditAnhydrous 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 nbsp Structure of solid SnCl4 Reactions EditTin 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 EditPrecursor to organotin compounds Edit 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 MgCl2Anhydrous tin IV chloride reacts with tetraorganotin compounds in redistribution reactions SnCl4 SnR4 2 SnCl2R2These organotin halides are useful precursors to catalysts e g dibutyltin dilaurate and polymer stabilizers 6 Organic synthesis Edit 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 EditStannic 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 References Edit a b c Egon Wiberg Nils Wiberg Arnold Frederick Holleman 2001 Inorganic Chemistry Elsevier ISBN 0 12 352651 5 a href Template Cite book html title Template Cite book cite book a CS1 maint multiple names authors list link Reuter Hans Pawlak Rudiger April 2000 Die Molekul und Kristallstruktur von Zinn IV chlorid Zeitschrift fur anorganische und allgemeine Chemie in German 626 4 925 929 doi 10 1002 SICI 1521 3749 200004 626 4 lt 925 AID ZAAC925 gt 3 0 CO 2 R Barnes John C Sampson Hazel A Weakley Timothy J R 1980 Structures of di m hydroxobis aquatrichlorotin IV 1 4 dioxane 1 3 di m hydroxobis aquatrichlorotin IV 1 8 epoxy p menthane 1 4 di m hydroxobis aquatribromotin IV 1 8 epoxy p menthane 1 4 di m hydroxobis aquatrichlorotin IV and cis diaquatetrachlorotin IV J Chem Soc Dalton Trans 6 949 doi 10 1039 DT9800000949 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 Greenwood Norman N Earnshaw Alan 1997 Chemistry of the Elements 2nd ed Butterworth Heinemann ISBN 978 0 08 037941 8 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 John R Johnson G E May 1938 2 Acetothienone Organic Syntheses 18 1 doi 10 15227 orgsyn 018 0001 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 Fries Amos A 2008 Chemical Warfare Read pp 148 49 407 ISBN 978 1 4437 3840 8 External links Edit nbsp Wikimedia Commons has media related to Tin IV chloride International Chemical Safety Card 0953 tinchemical com products industrial uses at the Wayback Machine archived 2005 02 28 Retrieved from https en wikipedia org w index php title Tin IV chloride amp oldid 1156165070, wikipedia, wiki, book, books, library,
