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91166-50-6

91166-50-6 Structure

91166-50-6 Structure
IdentificationMore
[Name]

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

91166-50-6
[Synonyms]

BIS(DIMETHYLAMINODIMETHYLSILYL)ETHANE
1,2-bis((diethylamino)dimethylsilyl)ethane
1,2-BIS[(DIMETHYLAMINO)DIMETHYLSILYL]ETHANE
1,1'-ETHYLENEBIS(N,N,1,1-TETRAMETHYLSILANAMIDE)
1,1'-ETHYLENEBIS(N,N,1,1-TETRAMETHYLSILANAMINE)
α,α'-Ethylenebis(N,N,α,α-tetramethylsilanamine)
[Protecting Reagent for Aromatic Primary Amines]
1,2-Bis[(dimethylamino)dimethylsilyl]ethane 
2,5-Bis(dimethylamino)-2,5-dimethyl-2,5-disilahexane
1,1'-(Ethane-1,2-diyl)bis(N,N,1,1-tetramethylsilanamine)
Silanamine, 1,1'-(1,2-ethanediyl)bis[N,N,1,1-tetramethyl-
1,4-BIS(DIMETHYLAMINO)-1,1,4,4-TETRAMETHYL-1,4-DISILABUTANE
N-[2-[dimethylamino(dimethyl)silyl]ethyl-dimethylsilyl]-N-methylmethanamine
1,2-Bis[(dimethylamino)dimethylsilyl]ethane [Protecting Reagent for Aromatic Primary Amines]
1,2-Bis[(dimethylamino)dimethylsilyl]ethane [Protecting Reagent for Aromatic Primary Amines]>
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
[Molecular Formula]

C10H28N2Si2
[MDL Number]

MFCD00010649
[Molecular Weight]

232.51
[MOL File]

91166-50-6.mol
Chemical PropertiesBack Directory
[Boiling point ]

101-103 °C13 mm Hg(lit.)
[density ]

0.824 g/mL at 25 °C(lit.)
[refractive index ]

n20/D 1.446(lit.)
[Fp ]

57 °F
[form ]

clear liquid
[pka]

10.31±0.70(Predicted)
[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)
Safety DataBack Directory
[Hazard Codes ]

F,C
[Risk Statements ]

R11:Highly Flammable.
R34:Causes burns.
[Safety Statements ]

S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
[RIDADR ]

UN 2924 3/PG 2
[WGK Germany ]

3
[F ]

10-21
[TSCA ]

No
[HazardClass ]

3.1
[PackingGroup ]

II
[HS Code ]

29319019
Hazard InformationBack Directory
[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.
[storage]

The liquid vapors are heavier than air and may travel a considerable distance to a source of ignition. Vapor-air mixtures are explosive above the flash point of 14 °C. Use in a fume hood.
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

91166-50-6(sigmaaldrich)
[TCI AMERICA]

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