Home Categories Analytical Chemistry 1,2-Bis[(dimethylamino)dimethylsilyl]ethane [Protecting Reagent for Aromatic Primary Amines]
A1602512

1,2-Bis[(dimethylamino)dimethylsilyl]ethane [Protecting Reagent for Aromatic Primary Amines] , >93.0%(GC) , 91166-50-6

CAS NO.:91166-50-6

Empirical Formula: C10H28N2Si2

Molecular Weight: 232.51

MDL number: MFCD00010649

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Update time: 2022-07-08

PRODUCT 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)

Description and 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).

Safety

Symbol(GHS) 
GHS02,GHS05
Signal word  Danger
Hazard statements  H225-H314
Precautionary statements  P233-P240-P241+P242+P243-P260-P264-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P403+P235-P405-P501-P210-P280-P305+P351+P338-P310
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

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