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1,2-BIS[(DIMETHYLAMINO)DIMETHYLSILYL]ETHANE

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1,2-BIS[(DIMETHYLAMINO)DIMETHYLSILYL]ETHANE Basic information

Product Name:
1,2-BIS[(DIMETHYLAMINO)DIMETHYLSILYL]ETHANE
Synonyms:
  • 1,1'-ETHYLENEBIS(N,N,1,1-TETRAMETHYLSILANAMIDE)
  • 1,1'-ETHYLENEBIS(N,N,1,1-TETRAMETHYLSILANAMINE)
  • 1,2-BIS[(DIMETHYLAMINO)DIMETHYLSILYL]ETHANE
  • 1,4-BIS(DIMETHYLAMINO)-1,1,4,4-TETRAMETHYL-1,4-DISILABUTANE
  • BIS(DIMETHYLAMINODIMETHYLSILYL)ETHANE
  • 1,2-Bis[(dimethylamino)dimethylsilyl]ethane [Protecting Reagent for Aromatic Primary Amines]
  • 1,2-bis((diethylamino)dimethylsilyl)ethane
  • 1,1μ-Ethylenebis(N,N,1,1-tetramethylsilanamine), 1,4-Bis(dimethylamino)-1,1,4,4-tetramethyl-1,4-disilabutane, 2,5-Bis(dimethylamino)-2,5-dimethyl-2,5-disilahexane
CAS:
91166-50-6
MF:
C10H28N2Si2
MW:
232.51
Product Categories:
  • Organosilicon
  • Others
  • Aminosilanes
  • Protection & Derivatization Reagents (for Synthesis)
  • Si (Classes of Silicon Compounds)
  • Si-N Compounds
  • Synthetic Organic Chemistry
  • Chemical Synthesis
  • Organometallic Reagents
Mol File:
91166-50-6.mol
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1,2-BIS[(DIMETHYLAMINO)DIMETHYLSILYL]ETHANE Chemical Properties

Boiling point:
101-103 °C13 mm Hg(lit.)
Density 
0.824 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.446(lit.)
Flash point:
57 °F
pka
10.31±0.70(Predicted)
form 
clear liquid
color 
Colorless to Almost colorless
Specific Gravity
0.824
Hydrolytic Sensitivity
8: reacts rapidly with moisture, water, protic solvents
BRN 
4366167
CAS DataBase Reference
91166-50-6(CAS DataBase Reference)
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Safety Information

Hazard Codes 
F,C
Risk Statements 
11-34
Safety Statements 
16-26-36/37/39-45
RIDADR 
UN 2924 3/PG 2
WGK Germany 
3
10-21
TSCA 
No
HazardClass 
3.1
PackingGroup 
II
HS Code 
29319019

MSDS

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1,2-BIS[(DIMETHYLAMINO)DIMETHYLSILYL]ETHANE Usage And Synthesis

Physical properties

bp 100–103°C/13 mmHg; d 0.824 g cm?3.

Uses

1,4-Bis(dimethylamino)-1,1,4,4-tetramethyldisilethylene is used as a reagent for the protection of primary amines with lower pKa values, such as substituted anilines, as their tetramethyldisilylazacyclopentane or Stabase adduct; precursor of tetramethyldisilylthiacyclopentane, a sulfur transfer reagent.
The title reagent is used for the preparation of Stabase derivatives of primary amines, and is particularly useful for the protection of primary aromatic amines with pKa values of 10–11. The protection of substituted anilines is achieved by heating equimolar amounts of the title compound and the anilines in the presence of zinc iodide (0.5 mol %) under a slow stream of nitrogen at 140°C for 5 h. In many cases the products can be purified by vacuum distillation. Cleavage of the Stabase adducts to the corresponding primary amines can be performed in ether in the presence of 2 equiv of methanol and a small amount of p-toluenesulfonic acid monohydrate (0.2 mol %). The tetramethyldisilylazacyclopentane or Stabase adduct (3) is a particularly attractive protecting group due to its ease of preparation, base stability, and facile removal (eq 1).

Preparation

the reagent is prepared as a colorless liquid in 90% yield by treating commercially available bis(chlorodimethylsilyl) ethane with 5 equiv of dimethylamine in ether at 0°C for 5 h.

1,2-BIS[(DIMETHYLAMINO)DIMETHYLSILYL]ETHANESupplier

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