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.)

Flash point:

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

Safety Information

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

MSDS

• Language:English Provider:SigmaAldrich

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[1]Burnell-Curty, C.; Roskamp, E. J. unpublished results.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.

BIS[BIS(TRIMETHYLSILYL)AMINO]TIN II(59863-13-7)Related Product Information

• Tin
• BIS[BIS(TRIMETHYLSILYL)AMINO]TIN II