661-69-8

Basic information

• Product Name: Hexamethyldistannane
• Synonyms: HEXAMETHYLDISTANNANE;HEXAMETHYLDITIN;HEXAMETHYLDITIN(IV);((CH3)3Sn)2;1,1,1,2,2,2-Hexamethyldistannane;1,1,1,2,2,2-Hexamethyl-distannane;Distannane, hexamethyl-;hexamethyl-distannan
• CAS NO: 661-69-8
• Molecular Formula: C₆H₁₈Sn₂
• Molecular Weight: 327.63
• EINECS: 211-549-2
• Product Categories: Organoditins;Organometallic Reagents;Organotin;organotin compound
• Mol File: 661-69-8.mol
• Article Data: 55

Chemical Properties

• Melting Point: 23-24 °C(lit.)
• Boiling Point: 182 °C756 mm Hg(lit.)
• Flash Point: 142 °F
• Appearance: colorless, low-melting/solid
• Density: 1.58 g/mL at 20 °C(lit.)
• Vapor Pressure: 1.35mmHg at 25°C
• Refractive Index: n20/D 1.540
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Not miscible or difficult to mix in water.
• Sensitive: Air Sensitive
• BRN: 3600327
• CAS DataBase Reference: Hexamethyldistannane(CAS DataBase Reference)
• NIST Chemistry Reference: Hexamethyldistannane(661-69-8)
• EPA Substance Registry System: Hexamethyldistannane(661-69-8)

Safety Data

• Hazard Codes: T+,N
• Statements: 26/27/28-50/53
• Safety Statements: 26-27-28-45-60-61-28A
• RIDADR: UN 3146 6.1/PG 2
• WGK Germany: 2
• RTECS: WH8280000
• F: 10-23
• TSCA: No
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 661-69-8(Hazardous Substances Data)

Usage

Description

It has been generally used as raw materials for producing other compounds in organic synthesis. For example, it can react with 1,3-dienes highly regioand stereo-selectively in the presence of a catalytic amount of bis(dibenzylideneacetone)palladium to afford dimerization-double-stannation adducts in high yields.1 The synthesis of allytrimethylstannanes with high yields was demonstrated by reaction of hexamethyldistanne with a broad range of allylic compounds including allyl acetates and allyl halides in the presence of palladium complexes.2 By using this product, the direct stannylation of halopyridines and bipyridines can be accomplished by Pd catalysis.3 Besides, the addition of hexamethyldistannane to 1-alkynes was shown to yield the (Z)-1,2-Bis(Trimethylstannyl)-1-Alkenes in the presence of Pd complex.4

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.

Chemical Properties

Clear colorless liquid

Uses

Different sources of media describe the Uses of 661-69-8 differently. You can refer to the following data:
1. Agricultural chemical.
2. It is used to prepare aryl tin compounds for microwave-assisted Stille cross-coupling with halo pyridines or copper-mediated O-arylation of phenols.

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 
• 17946-71-3 lithium trimethylstannyl 
• 89566-54-1 1-chloro-4-iodobicyclo<2.2.2>octane 
• 89566-55-2 1-bromo-4-iodobicyclo<2.2.2>octane 
• 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 

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 articles and documents

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.

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.

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