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 
• 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 
• 594-36-5 2-methyl-2-butylchloride 
• 111-83-1 1-bromo-octane 
• 1631-73-8 trimethylstannane 
• 4111-54-0 lithium diisopropyl amide 
• 1199-95-7 1-(trimethylstannyl)-2-phenylethyne 
• 51220-36-1 (1-naphthylmethyl)trimethyltin 
• 17946-71-3 lithium trimethylstannyl 
• 768-32-1 trimethylphenylsilane 

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.

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.

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