Trimethyltin chloride

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.

Trimethyltin chloride

Names
Preferred IUPAC name Chlorotri(methyl)stannane
Other names Chlorotrimethylstannane Chlorotrimethyltin Trimethyl chlorostannane Trimethylchlorotin Trimethylstannyl chloride Trimethyltin chloride Trimethyltin monochloride
Identifiers
CAS Number	1066-45-1 Y
3D model (JSmol)	Interactive image
ChemSpider	13398 Y
ECHA InfoCard	100.012.653
EC Number	213-917-8
PubChem CID	14016
UNII	9E3BCA3684 Y
UN number	3146 2786
CompTox Dashboard (EPA)	DTXSID6042496
InChI 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
SMILES C[Sn](C)(C)Cl
Properties
Chemical formula	(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]
Pictograms
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 [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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.