Hexamethyldistannane
Hexamethyldistannane Basic information
- Product Name:
- Hexamethyldistannane
- Synonyms:
-
- HEXAMETHYLDISTANNANE
- HEXAMETHYLDITIN
- HEXAMETHYLDITIN(IV)
- NSC-227328
- HexaMethylditin, 99% 1GR
- Hexamethyldistannane Bis(trimethyltin)
- HexaMethylditin 99%
- Hexamethylditin ,98.5%
- CAS:
- 661-69-8
- MF:
- C6H18Sn2
- MW:
- 327.63
- EINECS:
- 211-549-2
- Product Categories:
-
- organotin compound
- Organoditins
- Organometallic Reagents
- Organotin
- Mol File:
- 661-69-8.mol
Hexamethyldistannane Chemical Properties
- Melting point:
- 23-24 °C (lit.)
- Boiling point:
- 182 °C/756 mmHg (lit.)
- Density
- 1.58 g/mL at 20 °C (lit.)
- refractive index
- n20/D 1.540
- Flash point:
- 142 °F
- storage temp.
- Inert atmosphere,Room Temperature
- form
- solid
- Specific Gravity
- 1.570
- color
- Colourless
- Water Solubility
- Not miscible or difficult to mix in water.
- Sensitive
- Air Sensitive
- Hydrolytic Sensitivity
- 7: reacts slowly with moisture/water
- BRN
- 3600327
- Exposure limits
- ACGIH: TWA 0.1 mg/m3; STEL 0.2 mg/m3 (Skin)
NIOSH: IDLH 25 mg/m3; TWA 0.1 mg/m3 - InChIKey
- CCRMAATUKBYMPA-UHFFFAOYSA-N
- CAS DataBase Reference
- 661-69-8(CAS DataBase Reference)
- NIST Chemistry Reference
- Hexamethylditin(661-69-8)
- EPA Substance Registry System
- Distannane, hexamethyl- (661-69-8)
Safety Information
- Hazard Codes
- T+,N
- Risk 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
- HS Code
- 29319090
- Toxicity
- LD50 oral in rat: 7690ug/kg
MSDS
- Language:English Provider:ACROS
- Language:English Provider:SigmaAldrich
- Language:English Provider:ALFA
Hexamethyldistannane Usage And Synthesis
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.
[5] H. YOSHIDA. ChemInform Abstract: Copper-Catalyzed α-Selective Hydrostannylation of Alkynes for the Synthesis of Branched Alkenylstannanes.[J]. ChemInform, 2015, 46 44. DOI:10.1002/chin.201544208.
[6] BO CHEN . Palladium-catalyzed carbonylative synthesis of acylstannanes from aryl iodides and hexamethyldistannane[J]. Journal of Organometallic Chemistry, 2020, 923: Article 121351. DOI:10.1016/j.jorganchem.2020.121351.
Chemical Properties
Clear colorless liquid
Uses
Agricultural chemical.
Uses
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.
Chemical Reactivity
Hexamethyldistannane is a good chemical reagent that can react with unsaturated alkanes (alkynes or alkenes) and aryl iodides to form organostannanes. For example, the reaction of alkynes with hexamethyldistannane produces branched trimethylstannyl olefins[5]. Using Pd(PPh3)4 as a catalyst and toluene as a solvent, aryl iodides and hexamethyldistannane are carbonylated to form acylstannanes at 60 °C and 10 bar CO for 16 hours. For easy separation and analysis, the resulting acylstannanes can be converted to the corresponding benzoic acids by simply stirring in air for 5 hours[6].
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.]
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