Trimethyltin chloride

Last updated
Trimethyltin chloride
Trimethyltin chloride.png
Trimethyltin chloride 3D ball.png
Names
Preferred IUPAC name
Chlorotri(methyl)stannane
Other names
  • Chlorotrimethylstannane
  • Chlorotrimethyltin
  • Trimethyl chlorostannane
  • Trimethylchlorotin
  • Trimethylstannyl chloride
  • Trimethyltin chloride
  • Trimethyltin monochloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.653 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 213-917-8
PubChem CID
UNII
UN number 3146 2786
  • InChI=1S/3CH3.ClH.Sn/h3*1H3;1H;/q;;;;+1/p-1 X mark.svgN
    Key: KWTSZCJMWHGPOS-UHFFFAOYSA-M X mark.svgN
  • InChI=1/3CH3.ClH.Sn/h3*1H3;1H;/q;;;;+1/p-1/rC3H9ClSn/c1-5(2,3)4/h1-3H3
    Key: KWTSZCJMWHGPOS-KMTPXCBSAM
  • C[Sn](C)(C)Cl
Properties
(CH3)3SnCl
Molar mass 199.27 g·mol−1
AppearanceWhite solid
Odor Malodorous
Melting point 38.5 °C (101.3 °F; 311.6 K) [1]
Boiling point 148 °C (298 °F; 421 K)
Hazards
GHS labelling: [2]
GHS-pictogram-skull.svg GHS-pictogram-pollu.svg
Danger
H300, H310, H330, H410
P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P320, P322, P330, P361, P363, P391, P403+P233, P405
NFPA 704 (fire diamond)
NFPA 704.svgHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
1
0
Flash point 97 °C (207 °F; 370 K)
Lethal dose or concentration (LD, LC):
12.6 mg/kg (oral, rat)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

Synthesis

Trimethyltin chloride can be prepared by the redistribution reaction of tetramethyltin with tin tetrachloride. [3]

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−). [4] For example, it is a precursor to vinyltrimethylstannane ((CH3)3SnCH=CH2) [5] and indenyltrimethylstanane (CH3)3SnC9H7 (see Transition metal indenyl complex): [6]

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: [7]

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

Related Research Articles

The Stille reaction is a chemical reaction widely used in organic synthesis. The reaction involves the coupling of two organic groups, one of which is carried as an organotin compound (also known as organostannanes). A variety of organic electrophiles provide the other coupling partner. The Stille reaction is one of many palladium-catalyzed coupling reactions.

<span class="mw-page-title-main">Wacker process</span> Chemical reaction

The Wacker process or the Hoechst-Wacker process refers to the oxidation of ethylene to acetaldehyde in the presence of palladium(II) chloride and copper(II) chloride as the catalyst. This chemical reaction was one of the first homogeneous catalysis with organopalladium chemistry applied on an industrial scale.

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

Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin–carbon bonds. 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.

The Hiyama coupling is a palladium-catalyzed cross-coupling reaction of organosilanes with organic halides used in organic chemistry to form carbon–carbon bonds. This reaction was discovered in 1988 by Tamejiro Hiyama and Yasuo Hatanaka as a method to form carbon-carbon bonds synthetically with chemo- and regioselectivity. The Hiyama coupling has been applied to the synthesis of various natural products.

<span class="mw-page-title-main">Schwartz's reagent</span> Chemical compound

Schwartz's reagent is the common name for the organozirconium compound with the formula (C5H5)2ZrHCl, sometimes called zirconocene hydrochloride or zirconocene chloride hydride, and is named after Jeffrey Schwartz, a chemistry professor at Princeton University. This metallocene is used in organic synthesis for various transformations of alkenes and alkynes.

Transmetalation (alt. spelling: transmetallation) is a type of organometallic reaction that involves the transfer of ligands from one metal to another. It has the general form:

<span class="mw-page-title-main">Organolead chemistry</span>

Organolead chemistry is the scientific study of the synthesis and properties of organolead compounds, which are organometallic compounds containing a chemical bond between carbon and lead. The first organolead compound was hexaethyldilead (Pb2(C2H5)6), first synthesized in 1858. Sharing the same group with carbon, lead is tetravalent.

Pivalic acid is a carboxylic acid with a molecular formula of (CH3)3CCO2H. This colourless, odiferous organic compound is solid at room temperature. Two abbreviations for pivalic acid are t-BuC(O)OH and PivOH. The pivalyl or pivaloyl group is abbreviated t-BuC(O).

<span class="mw-page-title-main">Boronic acid</span> Organic compound of the form R–B(OH)2

A boronic acid is an organic compound related to boric acid in which one of the three hydroxyl groups is replaced by an alkyl or aryl group. As a compound containing a carbon–boron bond, members of this class thus belong to the larger class of organoboranes.

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

Vinyl bromide is the organobromine compound with the formula CH2=CHBr. Classified as a vinyl halide, it is a colorless gas at room temperature. It is used as a reagent and a comonomer.

Organotellurium chemistry describes the synthesis and properties of organotellurium compounds, chemical compounds containing a carbon-tellurium chemical bond. Organotellurium chemistry is a lightly studied area, in part because of it having few applications.

<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">Sodium tetraphenylborate</span> Chemical compound

Sodium tetraphenylborate is the organic compound with the formula NaB(C6H5)4. It is a salt, wherein the anion consists of four phenyl rings bonded to boron. This white crystalline solid is used to prepare other tetraphenylborate salts, which are often highly soluble in organic solvents. The compound is used in inorganic and organometallic chemistry as a precipitating agent for potassium, ammonium, rubidium, and caesium ions, and some organic nitrogen compounds.

Organoplatinum chemistry is the chemistry of organometallic compounds containing a carbon to platinum chemical bond, and the study of platinum as a catalyst in organic reactions. Organoplatinum compounds exist in oxidation state 0 to IV, with oxidation state II most abundant. The general order in bond strength is Pt-C (sp) > Pt-O > Pt-N > Pt-C (sp3). Organoplatinum and organopalladium chemistry are similar, but organoplatinum compounds are more stable and therefore less useful as catalysts.

<span class="mw-page-title-main">Stannoxane</span>

Stannoxane is a functional group in organotin chemistry with the connectivity SnIV−O−SnIV. Aside from the oxide group, usually 3 or 4 other substituents are attached to tin. In aqueous or aquatic environments, most organotin compounds contain this group.

<span class="mw-page-title-main">Stannatrane</span>

A stannatrane is a tin-based atrane belonging to the larger class of organostannanes. Though the term stannatrane is often used to refer to the more commonly employed carbastannatrane, azastannatranes have also been synthesized. Stannatrane reagents offer highly selective methods for the incorporation of "R" substituents in complex molecules for late-stage diversification. These reagents differ from their tetraalkyl organostannane analogues in that there is no participation of dummy ligands in the transmetalation step, offering selective alkyl transfer in Stille Coupling reactions. These transmetalating agents are known to be air- and moisture-stable, as well as generally less toxic than their tetraalkyl counterparts.

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

Vinyllithium is an organolithium compound with the formula LiC2H3. A colorless or white solid, it is encountered mainly as a solution in tetrahydrofuran (THF). It is a reagent in synthesis of organic compounds, especially for vinylations.

<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">Vinyl tributyltin</span> Chemical compound

Vinyl tributyltin is an organotin compound with the formula Bu3SnCH=CH2 (Bu = butyl). It is a white, air-stable solid. It is used as a source of vinyl anion equivalent in Stille coupling reactions. As a source of vinyltin reagents, early work used vinyl trimethyltin, but trimethyltin compounds are avoided nowadays owing to their toxicity.

Miyaura borylation, also known as the Miyaura borylation reaction, is a named reaction in organic chemistry that allows for the generation of boronates from vinyl or aryl halides with the cross-coupling of bis(pinacolato)diboron in basic conditions with a catalyst such as PdCl2(dppf). The resulting borylated products can be used as coupling partners for the Suzuki reaction.

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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