| Identification | Back Directory | [Name]
BIS[BIS(TRIMETHYLSILYL)AMINO]TIN II | [CAS]
59863-13-7 | [Synonyms]
TIN II BIS(HEXAMETHYLDISILAZIDE)
bis[bis(trimethylsilyl)amino]tin
BIS[BIS(TRIMETHYLSILYL)AMINO]TIN II
TIN II BIS(BIS(TRIMETHYLSILYL)AMIDE)
BIS[BIS(TRIMETHYLSILYL)AMINO]TIN(ll), 95% | [Molecular Formula]
C12H36N2Si4Sn | [MDL Number]
MFCD00191794 | [MOL File]
59863-13-7.mol | [Molecular Weight]
439.48 |
| Chemical Properties | Back Directory | [Melting point ]
37-38 °C(lit.) | [Boiling point ]
112 °C0.05 mm Hg(lit.) | [density ]
1.136 g/mL at 25 °C(lit.) | [refractive index ]
n20/D 1.514(lit.) | [Fp ]
133 °F | [storage temp. ]
2-8°C | [solubility ]
sol hexane, benzene, Et2O, THF, acetonitrile | [form ]
liquid | [Specific Gravity]
1.136 | [Hydrolytic Sensitivity]
8: reacts rapidly with moisture, water, protic solvents |
| Hazard Information | Back Directory | [Uses]
Reagent for the conversion of aldehydes and ketones to N,N-dialkyleneamines. | [Synthesis Reference(s)]
[1]Burnell-Curty, C.; Roskamp, E. J. unpublished results. Schaeffer, C. D., Jr.; Myers, L. K.; Coley, S. M.; Otter, J. C.; Yoder, C. H. J. Chem. Educ. 1990, 67, 347.
| [reaction suitability]
core: tin | [Synthesis]
BIS[BIS(TRIMETHYLSILYL)AMINO]TIN II's synthesis method: a 500 mL round bottomed flask equipped with a nitrogen inlet was charged with 65 mL of dioxane and 40.1 g of anhydrous Tin(II) Chloride (0.21 mol). This suspension was allowed to stir for 30 min at rt, and was then treated with 71.0 g of Lithium Hexamethyldisilazide (0.43 mol) in several small portions. During the addition of LiN(TMS)2 the reaction mixture became warm and turned dark red-orange in color. A Vigreux column and vacuum distillation apparutus were attached to the flask, and it was heated at 35 °C for 45 min. The apparatus was then placed under vacuum (0.5 mmHg) and the bath warmed to 85 °C. The forerun, mainly dioxane, was collected with the help of a dry ice acetone bath. Bis[N,N-bis(trimethylsilyl)amino]tin(II) distilled as a bright red oil between 105-115 °C (80.4 g, 86%); this material solidified upon standing at rt.[1] | [Precautions]
BIS[BIS(TRIMETHYLSILYL)AMINO]TIN II is nonpyrophoric but should be handled under a nitrogen atmosphere, and stored in a refrigerator. Since the solid is very soluble in hexane, it is convenient to prepare a hexane solution which may then be transferred via conventional syringe techniques. It readily hydrolyzes to tin(II) oxide, which is of reputed low toxicity. Use in a fume hood.
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