Methyl tin trichloride

Structural formula
General
Surname	Methyl tin trichloride
other names	Trichloromethylstannane MMTC
Molecular formula	CH 3 Cl 3 Sn
Brief description	white crystals
External identifiers / databases
CAS number 993-16-8 EC number 213-608-8 ECHA InfoCard 100.012.371 PubChem 101940 Wikidata Q20054533
properties
Molar mass	240.1 g mol −1
Physical state	firmly
density	1.5 g cm −3
Melting point	48-51 ° C
boiling point	171 ° C
Vapor pressure	1.70 hPa (° C)
solubility	Easily soluble in water (1038 g l −1 at 20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 228-311 + 331-314-317-361d-400 P: 210-261-273-280-305 + 351 + 338-310
MAK	0.004 ml m −3 , 0.02 mg m −3 (mono- and dimethyltin compounds)
Toxicological data	1370 mg kg −1 ( LD 50 ,  rat ,  oral ) 90 mg l −1 ( EC 50 ,  Daphnia magna , 24 h ) 0.072 mg l −1 ( EC 50 ,  Skeletonema costatum , 72 h )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Methyltin trichloride is a chemical compound from the group of organotin compounds .

Extraction and presentation

Methyl tin trichloride can be prepared by reacting tin dichloride with methyl chloride in the presence of a catalyst such as tetraphenylphosphonium chloride or antimony trichloride :

${\displaystyle \mathrm {SnCl_{2}\ +\ ClCH_{3}\quad {\xrightarrow[{PR_{4}Cl}]{}}\ Cl_{3}SnCH_{3}\ \ \ R=Phenyl} }$

${\displaystyle \mathrm {SnCl_{2}\ +\ ClCH_{3}\quad {\xrightarrow[{SbCl_{3}}]{}}\ Cl_{3}SnCH_{3}} }$

Also, it may without catalyst in high yield from stannous chloride and methylene chloride in a sodium tetrachloroaluminate - molten salt are prepared at 280 ° C. Compared to the direct reaction of molten tin dichloride with methyl chloride, the use of the molten salt results in a higher reactivity and selectivity :.

${\displaystyle \mathrm {SnCl_{2}+\ ClCH_{3}\ {\xrightarrow[{NaAlCl_{4}}]{}}\ \ Cl_{3}SnCH_{3}\ } }$

properties

Methyltin trichloride is a flammable, moisture-sensitive solid with a flash point of 41 ° C. In the ¹¹⁹ Sn NMR spectrum it shows a signal at +21 ppm . In benzene it has a dipole moment of 3.77 Debye .

Safety instructions / toxicity

Like many other organic tin compounds, methyltin trichloride is classified as toxic and must therefore be handled with appropriate care. The toxic effect is particularly targeted on the kidneys and the central nervous system , and in higher doses also on the liver , adrenal glands , thymus , spleen , urinary bladder , testes and epididymis .

Individual evidence

1. ↑ ^{a b c d e f g h} data sheet Methyltin trichloride, 97% from Sigma-Aldrich , accessed on May 8, 2015 ( PDF ).
2. ↑ ^{a b c d e} methyl tin compounds . In: DFG (Ed.): The MAK Collection for Occupational Health and Safety . 2014, p. 3-9 , doi : 10.1002 / 3527600418.mb744031metd0056 .
3. ↑ ^{a b} Entry on trichloromethylstannane in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
4. ↑ Entry on trichloromethylstannanes in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
5. ↑ Patent US3519667 : Process for preparing mono-methyl or ethyltin trichloride. Published on March 29, 1968 , inventor Hechenbleikner Ingenuin, Molt Kenneth R.
6. ^ Didier Astruc: Organometallic Chemistry and Catalysis. Springer Science & Business Media, 2007, ISBN 978-3-540-46129-6 , p. 336 ( limited preview in Google book search).
7. ^ W. Lutz, W. Sundermeyer, W. Towae: Chemical reactions in molten salts. XVIII. The synthesis of methyl tin trichloride, CH ₃ SnCl ₃ . In: Journal of Inorganic and General Chemistry . tape 444 , no. 1 , September 1978, p. 21-29 , doi : 10.1002 / zaac.19784440102 .
8. ↑ A. v. Rumohr, W. Sundermeyer, W. Towae: Chemical reactions in molten salts. XIX. For the direct synthesis of dimethyltin dichloride, (CH ₃ ) ₂ SnCl ₂ . In: Journal of Inorganic and General Chemistry . tape 499 , no. 4 , April 1983, pp. 75-80 , doi : 10.1002 / zaac.19834990409 .
9. ↑ entry to METHYLTIN TRICHLORIDE at ChemicalBook , accessed on May 8, 2015.
10. ↑ Christoph Elschenbroich: Organometallchemie . 4th edition. TB. G. Teubner, Stuttgart / Leipzig / Wiesbaden 2003, ISBN 978-3-322-99393-9 , pp. 174 , doi : 10.1007 / 978-3-322-99393-9 .
11. ↑ Jörg Lorberth, Heinrich Nöth: Dipole moments of some organotin chlorides . In: Chemical Reports . tape 98 , no. 3 , March 1965, p. 969 , doi : 10.1002 / cber.19650980342 .