Trimethyltin chloride

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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.653 Edit this at Wikidata
EC Number
  • 213-917-8
UNII
UN number 3146 2786
  • InChI=1S/3CH3.ClH.Sn/h3*1H3;1H;/q;;;;+1/p-1 ☒N
    Key: KWTSZCJMWHGPOS-UHFFFAOYSA-M ☒N
  • 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
Appearance White 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]
GHS06: ToxicGHS09: Environmental hazard
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
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).
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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.[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

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.