661-69-8 Usage
Description
Hexamethyldistannane, also known as HMDS, is a colorless liquid with the chemical formula (CH3)3Sn-Sn(CH3)3. It is an organotin compound that has been widely used as a reagent in various chemical reactions and as a precursor for the synthesis of other organotin compounds. Due to its unique chemical properties, it has found applications in different industries, including agriculture and organic synthesis.
Uses
Used in Agricultural Chemicals:
Hexamethyldistannane is used as a raw material for the production of aryl tin compounds, which are essential in the development of agricultural chemicals. These compounds play a crucial role in enhancing the effectiveness of pesticides and other agrochemicals, contributing to improved crop protection and yield.
Used in Organic Synthesis:
Hexamethyldistannane is used as a reagent in the preparation of aryl tin compounds for microwave-assisted Stille cross-coupling with halo pyridines or copper-mediated O-arylation of phenols. This application is vital in the synthesis of complex organic molecules, which are essential in the pharmaceutical, chemical, and materials industries.
Used in the Synthesis of Allyltrimethylstannanes:
Hexamethyldistannane is used as a reagent in the synthesis of allytrimethylstannanes with high yields. This is achieved by reacting hexamethyldistannane with a broad range of allylic compounds, including allyl acetates and allyl halides, in the presence of palladium complexes. The resulting allytrimethylstannanes are valuable intermediates in the synthesis of various organic compounds.
Used in the Direct Stannylation of Halopyridines and Bipyridines:
Hexamethyldistannane is used as a reagent for the direct stannylation of halopyridines and bipyridines through Pd catalysis. This process allows for the formation of organotin compounds that are essential in the development of new materials and pharmaceuticals.
Used in the Synthesis of (Z)-1,2-Bis(Trimethylstannyl)-1-Alkenes:
Hexamethyldistannane is used in the addition reaction to 1-alkynes, yielding the (Z)-1,2-Bis(Trimethylstannyl)-1-Alkenes in the presence of a Pd complex. These products are valuable intermediates in the synthesis of various organic compounds and materials.
Reference
Tsuji, Y.; Kakehi, T., PALLADIUM-CATALYZED DIMERIZATION DOUBLE STANNATION OF 1,3-DIENES USING HEXAMETHYLDISTANNANE. J. Chem. Soc.-Chem. Commun. 1992, 1000-1001.
Bumagin, N. A.; Kasatkin, A. N.; Beletskaya, I. P., REACTIONS OF HEXAMETHYLDISTANNANE WITH ALLYL ACETATES AND ALLYL HALIDES CATALYZED BY PALLADIUM COMPLEXES. Bulletin of the Academy of Sciences of the Ussr Division of Chemical Science 1984, 33, 588-594.
Benaglia, M.; Toyota, S.; Woods, C. R.; Siegel, J. S., Synthesis of pyridylstannanes from halopyridines and hexamethyldistannane with catalytic palladium. Tetrahedron Lett. 1997, 38, 4737-4740.
Mitchell, T. N.; Amamria, A.; Killing, H.; Rutschow, D., SYNTHESIS OF (Z)-1,2-BIS(TRIMETHYLSTANNYL)-1-ALKENES BY PLATINUM-CATALYZED ADDITION OF HEXAMETHYLDISTANNANE TO 1-ALKYNES. J. Organomet. Chem. 1983, 241, C45-C47.
Hazard
A poison by ingestion.
Purification Methods
Wash it with H2O and extract with *C6H6, dry by filtering through powdered Na2SO4, remove *C6H6 on a rotary evaporator and fractionally distil the oily residue under vacuum (b 85-88o/45mm). It boils at ca 182o at atmospheric pressure, but it cannot be distilled in air because the hot vapours flash in the condenser. [Kraus & Session J Am Chem Soc 47 2361 1925, Morris & Selwood J Am Chem Soc 63 2509 1941, Pedley et al. Trans Faraday Soc 53 1612 1957, Beilstein 4 IV 4346.]
Check Digit Verification of cas no
The CAS Registry Mumber 661-69-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,6 and 1 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 661-69:
(5*6)+(4*6)+(3*1)+(2*6)+(1*9)=78
78 % 10 = 8
So 661-69-8 is a valid CAS Registry Number.
InChI:InChI=1/6CH3.2Sn/h6*1H3;;/rC6H18Sn2/c1-7(2,3)8(4,5)6/h1-6H3
661-69-8Relevant articles and documents
Magnetic isotope effect in the photolysis of organotin compounds
Buchachenko, Anatoly L.,Ivanov, Vladimir L.,Roznyatovsky, Vitaly A.,Ustynyuk, Yuri A.
, p. 3857 - 3859 (2006)
Photolysis of organotin molecules RSnMe3 is shown to be a spin selective radical reaction accompanied by fractionation of magnetic, 117,119Sn, and nonmagnetic, 118,120Sn, isotopes between starting reagents and products. A primary photolysis process is a homolytic cleavage of the C-Sn bond and generation of a triplet radical pair as a spin-selective nanoreactor. Nuclear spin dependent triplet-singlet conversion of the pair results in the tin isotope fractionation. Experimentally detected isotope distribution unambiguously demonstrates that the classical, mass-dependent isotope effect is negligible in comparison with magnetic, spin-dependent isotope effect.
Reaction of α-(trialkylstannyl)acetylenes with metallic sodium
Komarov, N. V.,Andreev, A. A.,Shein, O. G.
, (1994)
α-Trialkylstannylacetylenes react under mild conditions with metallic sodium at the Sn-C(sp) bond to give hexaalkyldistannanes and sodium acetylalkynides in ca. 65 - 85percent yields. - Key words: α-(trialkylstannyl)acetylenes, reaction with sodium; hexaa
Chemically induced magnetic isotope effect on the tin nuclei during the photolysis of (1-fluorenyl)trimethyltin
Buchachenko,Roznyatovskii,Ivanov,Ustynyuk
, p. 1009 - 1010 (2006)
A magnetic isotope effect on the 117Sn and 119Sn nuclei, accompanied by the fractionation of magnetic and nonmagnetic tin isotopes, was observed during the photolysis of (9-fluorenyl)trimethyltin. The magnetic and nonmagnetic isotopes were accumulated, respectively, in the initial compound and a photolysis product (hexamethyldistannane). Nauka/Interperiodica 2006.
A simple synthesis of hexamethyldistannane from bis(trimethylstannyl)sulphide
Capozzi, Giuseppe,Menichetti, Stefano,Ricci, Alfredo,Taddei, Maurizio
, p. 285 - 288 (1988)
A new and cheap synthesis of hexamethyldistannane has been devised starting from bis(trimethylstannyl)sulphide, itself prepared a new method.
Reactions of a Zn(i) complex with group 14 azides-formation of zinc azide and zinc hexazene complexes
Gondzik,Schulz,Blaeser,Woelper,Haack,Jansen
supporting information, p. 927 - 929 (2014/01/06)
Two zinc hexazene complexes L2Zn2(μ-1,6-R 2-N6) (L = HC[C(Me)N(2,4,6-Me3C 6H2)]2; R = Ph (3), Dipp = 2,6-i-Pr 2C6H3 (4)), were synthesized by reaction of the Zn(i) complex L2Zn2 (1) with phenyl azide and 2,6-diisopropylphenyl azide, respectively. 3 represents the second structurally characterized transition metal hexazene complex. In contrast, reactions of 1 with Me3MN3 (M = Si, Sn) yielded the azido complex [LZn(μ-N3)]2 (2) and Me3M-MMe3.
Synthesis of 1-stannacyclopent-3-enes and their pyrolysis to stannylenes
Zhou, Dong,Reiche, Clemens,Nag, Mrinmoy,Soderquist, John A.,Gaspar, Petet P.
, p. 2595 - 2608 (2009/10/01)
1,1-Diorgano-1-stannacyclopent-3-enes have been synthesized by condensation in THF of magnesium complexes of 1,3-dienes and dichlorodiorganostannanes. 1,1-Dimethyl-, 1,1-di-n-butyl-, 1,1-di-tert-butyl-, and 1,1-diphenyl-1- stannacyclopent-3-enes and 1,1,3