BIS[BIS(TRIMETHYLSILYL)AMINO]TIN II Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H228Flammable solid

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

BIS[BIS(TRIMETHYLSILYL)AMINO]TIN II Chemical Properties,Usage,Production

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[1]Burnell-Curty, C.; Roskamp, E. J. unpublished results.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