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{{chembox |
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| verifiedrevid = 386316389 |
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| ImageFile=trimethyltin chloride.png |
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| verifiedrevid = 433077897 |
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| ImageSize=100px |
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| ImageFileL1 =trimethyltin chloride.png |
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| OtherNames = chlorotrimethylstannane; chlorotrimethyltin; trimethyl chlorostannane; trimethylchlorotin; trimethylstannyl chloride; trimethyltin monochloride |
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| ImageSizeL1 = 100px |
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| Section1 = {{Chembox Identifiers |
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| ImageAltL1 = Skeletal formula of trimethyltin chloride |
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| CASNo = 1066-45-1 |
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| ImageFileR1 = Trimethyltin chloride 3D ball.png |
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| ImageSizeR1 = 120 |
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| ImageAltR1 = Ball-and-stick model of the trimethyltin chloride molecule |
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| PIN = Chlorotri(methyl)stannane |
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| OtherNames = {{ubl|Chlorotrimethylstannane|Chlorotrimethyltin|Trimethyl chlorostannane|Trimethylchlorotin|Trimethylstannyl chloride|Trimethyltin chloride|Trimethyltin monochloride}} |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 1066-45-1 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 13398 |
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| EC_number = 213-917-8 |
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| PubChem = 14016 |
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| UNNumber = 3146 2786 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 9E3BCA3684 |
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| InChI = 1/3CH3.ClH.Sn/h3*1H3;1H;/q;;;;+1/p-1/rC3H9ClSn/c1-5(2,3)4/h1-3H3 |
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| InChIKey = KWTSZCJMWHGPOS-KMTPXCBSAM |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/3CH3.ClH.Sn/h3*1H3;1H;/q;;;;+1/p-1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = KWTSZCJMWHGPOS-UHFFFAOYSA-M |
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| SMILES = C(C)(C)Cl |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>3</sub>H<sub>9</sub>SnCl |
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| Formula = {{chem2|(CH3)3SnCl}} |
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| C=3|H=9|Sn=1|Cl=1 |
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| MolarMass = 199.27 g/mol |
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| Appearance = White solid |
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| MeltingPt = 38.5 °C (311.65 K)<ref> Lide, David R & Milne, G.W.A. Handbook of Data on Organic Compounds. 3<sup>rd</sup> Edition. Volume IV. CRC Press: 1994. pg 4973. </ref> |
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| Odor = Malodorous |
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| BoilingPt = 148 °C (421.15 K) |
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| MeltingPtC = 38.5 |
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| MeltingPt_ref =<ref>{{ cite book |author1=Lide, D. R. |author2=Milne, G. W. | title = Handbook of Data on Organic Compounds | edition = 3rd | volume = 4 | publisher = CRC Press | year = 1994 | page = 4973 }}</ref> |
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| BoilingPtC = 148 |
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| BoilingPt_notes = |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| GHS_ref=<ref>{{cite web |title=Trimethyltin chloride |url=https://pubchem.ncbi.nlm.nih.gov/compound/14016#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=12 December 2021 |language=en}}</ref> |
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| RPhrases = 26/27/28-50/53 |
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| GHSPictograms = {{GHS06}}{{GHS09}} |
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| SPhrases = 26-27-28-45-60-61 |
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| GHSSignalWord = Danger |
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| ExternalMSDS = |
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| HPhrases = {{H-phrases|300|310|330|410}} |
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| PPhrases = {{P-phrases|260|262|264|270|271|273|280|284|301+310|302+350|304+340|310|320|322|330|361|363|391|403+233|405}} |
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'''Trimethyltin chloride''' is an ] compound]] with the formula (CH<sub>3</sub>)<sub>3</sub>SnCl. It is a white solid that is highly toxic and has a stench. It is susceptible to ]. |
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'''Trimethyltin chloride''' is an ] compound with the formula {{chem2|(CH3)3SnCl}}. It is a white solid that is highly toxic and malodorous. It is susceptible to ]. |
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==Synthesis== |
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==Synthesis== |
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Trimethyltin chloride can be prepared by the ] of ] with ].<ref>{{OrgSynth | author = Scott, William J. Crisp, G. T., Stille, J. K. | title = Palladium-catalyzed Coupling of Vinyl Triflates with Organostannanes: 4-''tert''-Butylcyclohexen-1-yl)-2-propen-1-one | collvol = 8 | collvolpages = 97 | prep = cv8p0097 | year = 1993}}</ref> |
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Trimethyltin chloride can be prepared by the ] of ] with ].<ref>{{OrgSynth | author1 = Scott, W. J. |author2=Crisp, G. T. |author3=Stille, J. K. | title = Palladium-catalyzed Coupling of Vinyl Triflates with Organostannanes: 4-''tert''-Butylcyclohexen-1-yl)-2-propen-1-one | year = 1990 | volume = 68 | pages = 116 | collvol = 8 | collvolpages = 97 | prep = cv8p0097}}</ref> |
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:SnCl<sub>4</sub> + 3 SnMe<sub>4</sub> → 4 Me<sub>3</sub>SnCl |
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:{{chem2|SnCl4 + 3 Sn(CH3)4 → 4 (CH3)3SnCl}} |
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This redistribution reaction is typically performed with no solvent because high temperatures are required and purification is simplified. |
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A second route to {{chem2|(CH3)3SnCl}} involves treating the corresponding ] (in the following reaction, trimethyltin hydroxide {{chem2|(CH3)3SnOH}}) with a halogenating agent such as ] or ] ({{chem2|SOCl2}}): |
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This is the ]. It is performed under an inert atmosphere, such as ], typically with no solvent. |
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:{{chem2|(CH3)3SnOH + HCl → (CH3)3SnCl + H2O}} |
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A second route to Me<sub>3</sub>SnCl involves treating the corresponding ] or oxide with a halogenating agent such as ] or ] (SOCl<sub>2</sub>): |
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:Me<sub>3</sub>SnOH + HCl → Me<sub>3</sub>SnCl + H<sub>2</sub>O |
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==Uses== |
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==Uses== |
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Trimethyltin chloride is used as a source of the trimethylstanyl group.<ref> Davies, A.G. "Tin Organometallics". Comprehensive Organometallic Chemistry III. Elsevier B.V.: 2008. pg 809-883 {{DOI|10.1016/B0-08-045047-4/00054-6}}</ref> For example, it is a precursor to vinyltrimethylstannane: |
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Trimethyltin chloride is used as a source of the trimethylstannyl group ({{chem2|(CH3)3Sn\s}}).<ref>{{ cite book | author = Davies, A. G. | chapter = Tin Organometallics | title = Comprehensive Organometallic Chemistry | volume = 3 | publisher = Elsevier | year = 2008 | pages = 809–883 | doi = 10.1016/B0-08-045047-4/00054-6 | isbn = 978-0-08-045047-6 }}</ref> For example, it is a precursor to vinyltrimethylstannane ({{chem2|(CH3)3SnCH\dCH2}})<ref>{{cite journal |doi=10.15227/orgsyn.068.0116|title=Palladium-Catalyzed Coupling of Vinyl Triflates with Organostannanes: 4-''tert''-Butyl-1-vinylcyclohexene and 1-(4-''tert''-Butylcyclohexen-1-yl)-2-propen-1-one |
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|author1=William J. Scott |author2=G. T. Crisp |author3=J. K. Stille|journal=Organic Syntheses|year=1990|volume=68|page=116}}</ref> and ]trimethylstanane {{chem2|(CH3)3SnC9H7}} (see ]):<ref>{{cite book|chapter=Monoindenyltrichloride Complexes of Titanium(IV), Zirconium(IV), and Hafnium(IV)|volume=32|pages=215–221|author1=Robert J. Morris |author2=Scott L. Shaw |author3=Jesse M. Jefferis |author4=James J. Storhoff |author5=Dean M. Goedde|title=Inorganic Syntheses |doi=10.1002/9780470132630.ch36|year= 1998|isbn=978-0-470-13263-0 }}</ref> |
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:CH<sub>2</sub>=CHMgBr + Me<sub>3</sub>SnCl → Me<sub>3</sub>SnCH=CH<sub>2</sub> |
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:{{chem2|CH2\dCHMgBr + (CH3)3SnCl → (CH3)3SnCH\dCH2 + MgBrCl}} |
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:{{chem2|LiC9H7 + (CH3)3SnCl → (CH3)3SnC9H7 + LiCl}} |
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Another example of a Grignard reagent reacting with Me<sub>3</sub>SnCl to form a tin-carbon bond is: |
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An example of an ] reagent reacting with {{chem2|(CH3)3SnCl}} to form a ] is: |
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:LiCH(SiMe<sub>3</sub>)(GeMe<sub>3</sub>) + Me<sub>3</sub>SnCl → Me<sub>3</sub>SnCH(SiMe<sub>3</sub>)(GeMe<sub>3</sub>) + LiCl |
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:{{chem2|LiCH(Si(CH3)3)(Ge(CH3)3) + (CH3)3SnCl → (CH3)3SnCH(Si(CH3)3)(Ge(CH3)3) + LiCl}} |
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Organotin compounds derived from Me<sub>3</sub>SnCl are useful in ], especially in ] reactions. Me<sub>3</sub>SnCl is a precursor to compounds used in PVC stabilization. |
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Organotin compounds derived from {{chem2|Me3SnCl}} are useful in ], especially in ] reactions. {{chem2|(CH3)3SnCl}} is a precursor to compounds used in ] stabilization. |
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Reduction of trimethyltin chloride with sodium gives hexamethylditin:<ref>{{cite book |last1=Eisch |first1=John J. |title=Organometallic Syntheses II |date=1981 |publisher=Academic Press |location=New York |isbn=0-12-234950-4 |pages=167}}</ref> |
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Reduction of trimethyltin chloride gives tin-tin bonds. |
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:{{chem2|2 Na + 2 (CH3)3SnCl → (CH3)3Sn\sSn(CH3)3 + 2 NaCl}} |
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:Me<sub>3</sub>SnM + Me<sub>3</sub>SnCl → Sn<sub>2</sub>Me<sub>6</sub> + MCl (M = metal) |
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==References== |
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==References== |
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