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HomeProduct name list1,2-BIS[(DIMETHYLAMINO)DIMETHYLSILYL]ETHANE

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

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

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

Physical properties

bp 100–103°C/13 mmHg; d 0.824 g cm?3.

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

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).tetramethyldisilylazacyclopentane

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.

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

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
form  clear liquid
pka 10.31±0.70(Predicted)
Specific Gravity 0.824
color  Colorless to Almost colorless
Hydrolytic Sensitivity 8: reacts rapidly with moisture, water, protic solvents
BRN  4366167
CAS DataBase Reference 91166-50-6(CAS DataBase Reference)

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

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Corrosion
Corrosives
GHS05
GHS Hazard Statements H225:Flammable liquids
H314:Skin corrosion/irritation
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P233:Keep container tightly closed.
P240:Ground/bond container and receiving equipment.
P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P310:Immediately call a POISON CENTER or doctor/physician.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.
P403+P235:Store in a well-ventilated place. Keep cool.
P501:Dispose of contents/container to..…

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

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