| Identification | More | [Name]
Hexamethyldistannane | [CAS]
661-69-8 | [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
hexamethyldi-stannan
in, hexamethyldi-
Pennsalt TD 5032
pennsalttd5032
rimethyltin dimer
Stannane, hexamethyldi-
TD 5032
td-5032
Hexamethylditin,97%
Hexamethylditin,95%
Hexamethylditin,99%
NSC-227328 | [EINECS(EC#)]
211-549-2 | [Molecular Formula]
C6H18Sn2 | [MDL Number]
MFCD00008277 | [Molecular Weight]
327.63 | [MOL File]
661-69-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear colorless liquid | [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
| [Fp ]
142 °F
| [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
solid | [color ]
colorless, low-melting | [Specific Gravity]
1.570 | [Water Solubility ]
Not miscible or difficult to mix in water. | [Hydrolytic Sensitivity]
7: reacts slowly with moisture/water | [Sensitive ]
Air Sensitive | [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 | [Uses]
Agricultural chemical. | [CAS DataBase Reference]
661-69-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Hexamethylditin(661-69-8) | [EPA Substance Registry System]
661-69-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T+,N | [Risk Statements ]
R26/27/28:Very Toxic by inhalation, in contact with skin and if swallowed .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S27:Take off immediately all contaminated clothing .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [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 |
| Hazard Information | Back Directory | [Hazard]
A poison by ingestion. | [Chemical Properties]
Clear colorless liquid | [Chemical Reactivity]
Hexamethyldistannane(661-69-8) 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.] |
| Questions And Answer | Back Directory | [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.
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