661-69-8

Usage

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.]

InChI:InChI=1/6CH3.2Sn/h6*1H3;;/rC6H18Sn2/c1-7(2,3)8(4,5)6/h1-6H3

Upstream product

• 16643-09-7 trimethylstannyl sodium 
• 6973-40-6 2,4,6-trinitrophenyl phenyl ether 
• 38423-82-4 potassium trimethylstannate 
• 16393-88-7 trimethyl(trimethylstannyl)silane 
• 106-38-7 para-bromotoluene 
• 1631-73-8 trimethylstannane 
• 4111-54-0 lithium diisopropyl amide 
• 7440-31-5 tin 
• 74-88-4 methyl iodide 
• 563-47-3 3-Chloro-2-methylpropene 
• 507-19-7 t-butyl bromide 
• 507-20-0 tertiary butyl chloride 
• 558-17-8 tert-Butyl iodide 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 

Downstream Products

• 4158-75-2 hexa-p-tolyldistannane 
• 121848-29-1 1,1,1-trimethyl-2,2,2-tri-p-tolyl distannane 
• 7070-08-8 (1R,4R)-1,7,7-Trimethyl-3-phenyl-bicyclo[2.2.1]hept-2-ene 
• 7070-09-9 (1R,4R)-1,7,7-trimethyl-2-phenylbicyclo[2.2.1]hept-2-ene 
• 92-52-4 biphenyl 
• 594-27-4 tetramethylstannane 
• 21942-04-1 trimethyltin picrate 
• 161767-56-2 meta-trimethylstannylbenzoic acid 
• 1528-74-1 4,4'-dinitrobiphenyl 
• 52323-94-1 trimethyl(4-nitrophenyl)stannane 
• 848469-54-5 (1R,2S,3S,5S)-3-(4-Thiophen-2-yl-phenyl)-8-aza-bicyclo[3.2.1]octane-2,8-dicarboxylic acid 2-methyl ester 8-(2,2,2-trichloro-ethyl) ester 
• 848469-63-6 (1R,2S,3S,5S)-3-(4-Thiophen-3-yl-phenyl)-8-aza-bicyclo[3.2.1]octane-2,8-dicarboxylic acid 2-methyl ester 8-(2,2,2-trichloro-ethyl) ester 
• 874379-31-4 2-acetyl-6-(trimethylstannyl)pyridine 
• 49669-27-4 6,6'-diacetyl-2,2'-bipyridine 

Relevant academic research and scientific papers

Magnetic isotope effect in the photolysis of organotin compounds

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

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

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.

The palladium-catalysed addition of hexamethylditin to 1,3-dienes

The addition of the tin-tin bond of hexamethylditin to some 1,3-dienes occurs readily in the presence of the catalyst system palladiumbis(dibenzylideneacetone)/triethyl phosphite.

A simple synthesis of hexamethyldistannane from bis(trimethylstannyl)sulphide

A new and cheap synthesis of hexamethyldistannane has been devised starting from bis(trimethylstannyl)sulphide, itself prepared a new method.

Microsolvation, aggregation, and pseudomonomolecular, ionic sp 2-stereoinversion mechanism of two exocyclic β,β-di-tert- alkyl-α-arylvinyllithiums This article is dedicated to Professor Paul Knochel in recognition of his kind support.

A THF-solvated, crystalline, exocyclic alkenyllithium, (tert-alkyl) 2CC(Li)-Ph, was synthesized and shown to be a disolvated dimer in the solid state and in toluene as the solvent; increasing amounts of the monomeric species emerged on cooling the toluene solution. In THF as the solvent, only the trisolvated monomer was present and identified as a contact ion pair (CIP) through its scalar 13C,6Li NMR coupling. This ground-state needs only one further THF ligand as a catalyst for breaking the C-Li bond with formation of a tetrasolvated, solvent-separated ion pair (SSIP) on the way to the transition state of cis/trans sp2-stereoinversion. The ensuing pseudomonomolecular, ionic mechanism is confirmed by low pseudoactivation parameters: enthalpy ΔHψ? = 6.9(3) kcal mol-1; entropy ΔSψ? = -23.3(9) cal mol-1 K-1. Similar parameters were found with 2,6-dimethylphenyl in place of Ph.

Reactions of a Zn(i) complex with group 14 azides-formation of zinc azide and zinc hexazene complexes

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.

Low-coordinate cobalt fluoride complexes: Synthesis, reactions, and production from C-F activation reactions

A cobalt(II) fluoride complex, [LtBuCo(μ-F)]2 [LtBu = 2,2,6,6-tetramethyl-3,5-bis(2,6-diisopropylphenylimido)hept- 4-yl], was synthesized from LtBuCo using Me3SnF via homolytic cleavage of the Sn-F bond. LtBuCo also performed the overall binuclear oxidative addition of fluorinated arenes to give [L tBuCo(μ-F)]2 and a cobalt(II) aryl complex of the corresponding fluorobenzene substrate in a 1:2 molar ratio. The C-F activation reaction has a first-order rate dependence on both cobalt and fluorobenzene concentrations. The rate is increased by meta-fluoride substituents, and slowed by ortho-fluoride substituents, suggesting electronic and steric influences on the transition state, respectively. The data are most consistent with a mechanism beginning with rate-limiting oxidative addition of the aryl fluoride to cobalt(I), followed by rapid reduction of the cobalt(III) aryl fluoride intermediate by a second molecule of LtBuCo. [LtBuCo(μ- F)]2 also reacts with Et3SiH to give the hydride complex [LtBuCo(μ-H)]2. This hydride complex has low reactivity toward alkenes and N2, in contrast to an earlier report.

Synthesis of 1-stannacyclopent-3-enes and their pyrolysis to stannylenes

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

Stereoselective radical tandem cyclohydrostannation of optically active di-unsaturated esters of TADDOL

This paper reports the results obtained in a study on the radical addition of triorganotin hydrides, R3SnH (R = Me, n-Bu, Ph; Neophyl), to four TADDOL unsaturated diesters. It was found that diese reactions lead in high yields to products of cyclohydrostannation. It was also found that whereas the addition of these hydrides to TADDOL diacrylate and TADDOL dimethacrylate leads to the expected mixtures of two and four cycloundecane diastereoisomers, respectively, the addition of triphenyltin hydride to TADDOL disubstituted acrylates yields only four out of the 16 possible stereoisomers. The observed high stereoselectivity is consistent with the radical tandem cyclohydrostannation mechanism proposed. Only in the case of the hydrostannation of TADDOL diacrylate with trimethyl- and triphenyltin hydrides could the diastereoisomers obtained in higher proportion (5a and 8a) be isolated in pure form. The subsequent reduction (lithium aluminum hydride) of macrolides 5a and 8a afforded the corresponding optically active diols 26 and 27 in high yield. Full 1H, 13C, and 119Sn NMR data are given.