BIS[BIS(TRIMETHYLSILYL)AMINO]TIN II

Product NameBIS[BIS(TRIMETHYLSILYL)AMINO]TIN II
CAS59863-13-7
MFC12H36N2Si4Sn
MW439.48
EINECS
MOL File59863-13-7.mol

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
InChI	1S/2C6H18NSi2.Sn/c21-8(2,3)7-9(4,5)6;/h21-6H3;/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

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
Storage Class	4.1B - Flammable solid hazardous materials
Hazard Classifications	Eye Irrit. 2 Flam. Sol. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

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[1]Burnell-Curty, C.; Roskamp, E. J. unpublished results.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