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| | Bis[bis(trimethylsilyl)amino]tin II Basic information |
| | Bis[bis(trimethylsilyl)amino]tin II Chemical Properties |
| 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 | | InChI | 1S/2C6H18NSi2.Sn/c2*1-8(2,3)7-9(4,5)6;/h2*1-6H3;/q2*-1;+2 | | InChIKey | WLNIUEYAQZRJFS-UHFFFAOYSA-N | | SMILES | C[Si](C)(C)N([SnH2]N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | RIDADR | UN 1325 4.1/PG 2 | | WGK Germany | 3 | | TSCA | No | | HazardClass | 4.1 | | PackingGroup | III | | Storage Class | 4.1B - Flammable solid hazardous materials | | Hazard Classifications | Eye Irrit. 2
Flam. Sol. 2
Skin Irrit. 2
STOT SE 3 |
| | Bis[bis(trimethylsilyl)amino]tin II Usage And Synthesis |
| 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 | | Synthesis Reference(s) | [1]Burnell-Curty, C.; Roskamp, E. J. unpublished results.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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| | Bis[bis(trimethylsilyl)amino]tin II Preparation Products And Raw materials |
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