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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 386316389
| Watchedfields = changed
⚫ | ImageFile=trimethyltin chloride.png
⚫ | verifiedrevid = 433077897
| ImageSize=100px
⚫ | ImageFileL1 =trimethyltin chloride.png
| OtherNames = chlorotrimethylstannane; chlorotrimethyltin; trimethyl chlorostannane; trimethylchlorotin; trimethylstannyl chloride; trimethyltin monochloride
| ImageSizeL1 = 100px
⚫ | Section1 = {{Chembox Identifiers
| ImageAltL1 = Skeletal formula of trimethyltin chloride
⚫ | CASNo = 1066-45-1
| ImageFileR1 = Trimethyltin chloride 3D ball.png
| ImageSizeR1 = 120
| ImageAltR1 = Ball-and-stick model of the trimethyltin chloride molecule
| PIN = Chlorotri(methyl)stannane
| OtherNames = {{ubl|Chlorotrimethylstannane|Chlorotrimethyltin|Trimethyl chlorostannane|Trimethylchlorotin|Trimethylstannyl chloride|Trimethyltin chloride|Trimethyltin monochloride}}
⚫ |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo = 1066-45-1
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13398
| EC_number = 213-917-8
| PubChem = 14016
| UNNumber = 3146 2786
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9E3BCA3684
| InChI = 1/3CH3.ClH.Sn/h3*1H3;1H;/q;;;;+1/p-1/rC3H9ClSn/c1-5(2,3)4/h1-3H3
| InChIKey = KWTSZCJMWHGPOS-KMTPXCBSAM
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/3CH3.ClH.Sn/h3*1H3;1H;/q;;;;+1/p-1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = KWTSZCJMWHGPOS-UHFFFAOYSA-M
| SMILES = C(C)(C)Cl
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>3</sub>H<sub>9</sub>SnCl | Formula = {{chem2|(CH3)3SnCl}}
| C=3|H=9|Sn=1|Cl=1
| MolarMass = 199.27 g/mol
| Appearance = White solid
| 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>
| Odor = Malodorous
| BoilingPt = 148 °C (421.15 K)
| MeltingPtC = 38.5
| 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>
| BoilingPtC = 148
| BoilingPt_notes =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| 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>
| RPhrases = 26/27/28-50/53
| GHSPictograms = {{GHS06}}{{GHS09}}
| SPhrases = 26-27-28-45-60-61
| GHSSignalWord = Danger
⚫ | ExternalMSDS =
| HPhrases = {{H-phrases|300|310|330|410}}
| 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}}
⚫ | ExternalSDS =
}} }}
}} }}
'''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 ]. '''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 ].


==Synthesis== ==Synthesis==
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> 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>
:SnCl<sub>4</sub> + 3 SnMe<sub>4</sub> → 4 Me<sub>3</sub>SnCl :{{chem2|SnCl4 + 3 Sn(CH3)4 → 4 (CH3)3SnCl}}
This redistribution reaction is typically performed with no solvent because high temperatures are required and purification is simplified.


⚫ 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}}):
This is the ]. It is performed under an inert atmosphere, such as ], typically with no solvent.
:{{chem2|(CH3)3SnOH + HCl → (CH3)3SnCl + H2O}}

⚫ 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>):
:Me<sub>3</sub>SnOH + HCl → Me<sub>3</sub>SnCl + H<sub>2</sub>O


==Uses== ==Uses==
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: 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
|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>
:CH<sub>2</sub>=CHMgBr + Me<sub>3</sub>SnCl → Me<sub>3</sub>SnCH=CH<sub>2</sub>
:{{chem2|CH2\dCHMgBr + (CH3)3SnCl → (CH3)3SnCH\dCH2 + MgBrCl}}
:{{chem2|LiC9H7 + (CH3)3SnCl → (CH3)3SnC9H7 + LiCl}}


Another example of a Grignard reagent reacting with Me<sub>3</sub>SnCl to form a tin-carbon bond is: An example of an ] reagent reacting with {{chem2|(CH3)3SnCl}} to form a ] is:
: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 :{{chem2|LiCH(Si(CH3)3)(Ge(CH3)3) + (CH3)3SnCl → (CH3)3SnCH(Si(CH3)3)(Ge(CH3)3) + LiCl}}


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. Organotin compounds derived from {{chem2|Me3SnCl}} are useful in ], especially in ] reactions. {{chem2|(CH3)3SnCl}} is a precursor to compounds used in ] stabilization.
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>
Reduction of trimethyltin chloride gives tin-tin bonds.
:{{chem2|2 Na + 2 (CH3)3SnCl → (CH3)3Sn\sSn(CH3)3 + 2 NaCl}}
:Me<sub>3</sub>SnM + Me<sub>3</sub>SnCl → Sn<sub>2</sub>Me<sub>6</sub> + MCl (M = metal)


==References== ==References==
{{reflist}}
<references/>


] ]
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Latest revision as of 12:52, 2 September 2024

Trimethyltin chloride
Skeletal formula of trimethyltin chloride
Ball-and-stick model of the trimethyltin chloride molecule
Names
Preferred IUPAC name Chlorotri(methyl)stannane
Other names
  • Chlorotrimethylstannane
  • Chlorotrimethyltin
  • Trimethyl chlorostannane
  • Trimethylchlorotin
  • Trimethylstannyl chloride
  • Trimethyltin chloride
  • Trimethyltin monochloride
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.653 Edit this at Wikidata
EC Number
  • 213-917-8
PubChem CID
UNII
UN number 3146 2786
CompTox Dashboard (EPA)
InChI
  • InChI=1S/3CH3.ClH.Sn/h3*1H3;1H;/q;;;;+1/p-1Key: KWTSZCJMWHGPOS-UHFFFAOYSA-M
  • InChI=1/3CH3.ClH.Sn/h3*1H3;1H;/q;;;;+1/p-1/rC3H9ClSn/c1-5(2,3)4/h1-3H3Key: KWTSZCJMWHGPOS-KMTPXCBSAM
SMILES
  • C(C)(C)Cl
Properties
Chemical formula (CH3)3SnCl
Molar mass 199.27 g·mol
Appearance White solid
Odor Malodorous
Melting point 38.5 °C (101.3 °F; 311.6 K)
Boiling point 148 °C (298 °F; 421 K)
Hazards
GHS labelling:
Pictograms GHS06: ToxicGHS09: Environmental hazard
Signal word Danger
Hazard statements H300, H310, H330, H410
Precautionary statements P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P320, P322, P330, P361, P363, P391, P403+P233, P405
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
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.

Synthesis

Trimethyltin chloride can be prepared by the redistribution reaction of tetramethyltin with tin tetrachloride.

SnCl4 + 3 Sn(CH3)4 → 4 (CH3)3SnCl

This redistribution reaction is typically performed with no solvent because high temperatures are required and purification is simplified.

A second route to (CH3)3SnCl involves treating the corresponding hydroxide or oxide (in the following reaction, trimethyltin hydroxide (CH3)3SnOH) with a halogenating agent such as hydrogen chloride or thionyl chloride (SOCl2):

(CH3)3SnOH + HCl → (CH3)3SnCl + H2O

Uses

Trimethyltin chloride is used as a source of the trimethylstannyl group ((CH3)3Sn−). For example, it is a precursor to vinyltrimethylstannane ((CH3)3SnCH=CH2) and indenyltrimethylstanane (CH3)3SnC9H7 (see Transition metal indenyl complex):

CH2=CHMgBr + (CH3)3SnCl → (CH3)3SnCH=CH2 + MgBrCl
LiC9H7 + (CH3)3SnCl → (CH3)3SnC9H7 + LiCl

An example of an organolithium reagent reacting with (CH3)3SnCl to form a tin-carbon bond is:

LiCH(Si(CH3)3)(Ge(CH3)3) + (CH3)3SnCl → (CH3)3SnCH(Si(CH3)3)(Ge(CH3)3) + LiCl

Organotin compounds derived from Me3SnCl are useful in organic synthesis, especially in radical chain reactions. (CH3)3SnCl is a precursor to compounds used in PVC stabilization. Reduction of trimethyltin chloride with sodium gives hexamethylditin:

2 Na + 2 (CH3)3SnCl → (CH3)3Sn−Sn(CH3)3 + 2 NaCl

References

  1. Lide, D. R.; Milne, G. W. (1994). Handbook of Data on Organic Compounds. Vol. 4 (3rd ed.). CRC Press. p. 4973.
  2. "Trimethyltin chloride". pubchem.ncbi.nlm.nih.gov. Retrieved 12 December 2021.
  3. Scott, W. J.; Crisp, G. T.; Stille, J. K. (1990). "Palladium-catalyzed Coupling of Vinyl Triflates with Organostannanes: 4-tert-Butylcyclohexen-1-yl)-2-propen-1-one". Organic Syntheses. 68: 116; Collected Volumes, vol. 8, p. 97.
  4. Davies, A. G. (2008). "Tin Organometallics". Comprehensive Organometallic Chemistry. Vol. 3. Elsevier. pp. 809–883. doi:10.1016/B0-08-045047-4/00054-6. ISBN 978-0-08-045047-6.
  5. William J. Scott; G. T. Crisp; J. K. Stille (1990). "Palladium-Catalyzed Coupling of Vinyl Triflates with Organostannanes: 4-tert-Butyl-1-vinylcyclohexene and 1-(4-tert-Butylcyclohexen-1-yl)-2-propen-1-one". Organic Syntheses. 68: 116. doi:10.15227/orgsyn.068.0116.
  6. Robert J. Morris; Scott L. Shaw; Jesse M. Jefferis; James J. Storhoff; Dean M. Goedde (1998). "Monoindenyltrichloride Complexes of Titanium(IV), Zirconium(IV), and Hafnium(IV)". Inorganic Syntheses. Vol. 32. pp. 215–221. doi:10.1002/9780470132630.ch36. ISBN 978-0-470-13263-0.
  7. Eisch, John J. (1981). Organometallic Syntheses II. New York: Academic Press. p. 167. ISBN 0-12-234950-4.
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