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.
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):
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
^Lide, D. R.; Milne, G. W. (1994). Handbook of Data on Organic Compounds. Vol. 4 (3rd ed.). CRC Press. p. 4973.
^"Trimethyltin chloride". pubchem.ncbi.nlm.nih.gov. Retrieved 12 December 2021.
^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.; Collective Volume, vol. 8, p. 97
^Davies, A. G. (2008). "Tin Organometallics". Comprehensive Organometallic Chemistry. Vol. 3. Elsevier. pp. 809–883. doi:10.1016/B0-08-045047-4/00054-6. ISBN9780080450476.
^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.
^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. 32: 215–221. doi:10.1002/9780470132630.ch36.
^Eisch, John J. (1981). Organometallic Syntheses II. New York: Academic Press. p. 167. ISBN0-12-234950-4.
February 07, 2023
trimethyltin, chloride, organotin, compound, with, formula, 3sncl, white, solid, that, highly, toxic, malodorous, susceptible, hydrolysis, namespreferred, iupac, name, chlorotri, methyl, stannaneother, names, chlorotrimethylstannanechlorotrimethyltintrimethyl,. 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 NamesPreferred IUPAC name Chlorotri methyl stannaneOther names ChlorotrimethylstannaneChlorotrimethyltinTrimethyl chlorostannaneTrimethylchlorotinTrimethylstannyl chlorideTrimethyltin chlorideTrimethyltin monochlorideIdentifiersCAS Number 1066 45 1 Y3D model JSmol Interactive imageChemSpider 13398 YECHA InfoCard 100 012 653EC Number 213 917 8PubChem CID 14016UNII 9E3BCA3684 YUN number 3146 2786CompTox Dashboard EPA DTXSID6042496InChI InChI 1S 3CH3 ClH Sn h3 1H3 1H q 1 p 1 NKey KWTSZCJMWHGPOS UHFFFAOYSA M NInChI 1 3CH3 ClH Sn h3 1H3 1H q 1 p 1 rC3H9ClSn c1 5 2 3 4 h1 3H3Key KWTSZCJMWHGPOS KMTPXCBSAMSMILES C Sn C C ClPropertiesChemical formula CH3 3SnClMolar mass 199 27 g mol 1Appearance White solidOdor MalodorousMelting point 38 5 C 101 3 F 311 6 K 1 Boiling point 148 C 298 F 421 K HazardsGHS labelling 2 PictogramsSignal word DangerHazard statements H300 H310 H330 H410Precautionary statements P260 P262 P264 P270 P271 P273 P280 P284 P301 P310 P302 P350 P304 P340 P310 P320 P322 P330 P361 P363 P391 P403 P233 P405Safety data sheet SDS External MSDSExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesSynthesis EditTrimethyltin chloride can be prepared by the redistribution reaction of tetramethyltin with tin tetrachloride 3 SnCl4 3 Sn CH3 4 4 CH3 3SnClThis 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 H2OUses EditTrimethyltin 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 LiClAn 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 LiClOrganotin 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 NaClReferences Edit Lide D R Milne G W 1994 Handbook of Data on Organic Compounds Vol 4 3rd ed CRC Press p 4973 Trimethyltin chloride pubchem ncbi nlm nih gov Retrieved 12 December 2021 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 Collective Volume vol 8 p 97 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 9780080450476 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 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 32 215 221 doi 10 1002 9780470132630 ch36 Eisch John J 1981 Organometallic Syntheses II New York Academic Press p 167 ISBN 0 12 234950 4 Retrieved from https en wikipedia org w index php title Trimethyltin chloride amp oldid 1133120991, wikipedia, wiki, book, books, library,
