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Trimethyltin chloride

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
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 X markN
    Key: KWTSZCJMWHGPOS-UHFFFAOYSA-M X markN
  • 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, P330, P361, P363, P391, P403+P233, P405
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 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
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

Toxicity

The ototoxicity of trimethyltin chloride in humans is not conclusively known.[8]: 4  In guinea pigs, administered intraperitoneally, it is acutely and persistently ototoxic at 2 mg/kg (mechanisms may include damage to hair cells and vasculature of the cochlea), but in rats no such effect occurred.[8]: 4–8 

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