CAS 91166-50-6 1,2-Bis(Dimethylaminodimethylsilyl)Ethane

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1,2-Bis(Dimethylaminodimethylsilyl)Ethane

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Catalog Number

ACM91166506

CAS Number

91166-50-6

Product Name

1,2-Bis(Dimethylaminodimethylsilyl)Ethane

Structure

Category

Salt

Synonyms

1,2-Bis[(dimethylamino)dimethylsilyl]ethane, 1,1-Ethylenebis(N,N,1,1-tetramethylsilanamine), 91166-50-6, 2,5-Bis(dimethylamino)-2,5-dimethyl-2,5-disilahexane, 1,4-Bis(dimethylamino)-1,1,4,4-tetramethyl-1,4-disilabutane, AC1N4ZJ6, 324639_ALDRICH, CTK8E3105, AKOS015895013, B1773, FT-0642190, I05-3359, 1,1 inverted exclamation marka-Ethylenebis(N,N,1,1-tetramethylsilanamine), N-[2-[dimethylamino(dimethyl)silyl]ethyl-dimethylsilyl]-N-methylmethanamine

IUPAC Name

N-[2-[dimethylamino(dimethyl)silyl]ethyl-dimethylsilyl]-N-methylmethanamine

Molecular Weight

232.52 g/mol

Molecular Formula

C10H28N2Si2

Canonical SMILES

CN(C)[Si](C)(C)CC[Si](C)(C)N(C)C

InChI Key

MRAAXSSHMOFDJR-UHFFFAOYSA-N

Boiling Point

101-103ºC13 mm Hg(lit.)

Flash Point

57 °F

Purity

95%+

Density

0.824 g/mL at 25ºC(lit.)

Appearance

Transparent liquid

Application

1,2-Bis(Dimethylaminodimethylsilyl)Ethane serves as a versatile reagent primarily aimed at protecting primary aromatic amines, particularly those with pKa values around 10-11, such as substituted anilines. The compound is instrumental in forming Stabase derivatives, which provide a robust yet easily removable protecting group. To achieve this protection, equimolar amounts of 1,2-Bis(Dimethylaminodimethylsilyl)Ethane and anilines are combined in the presence of zinc iodide under nitrogen, heated at 140°C for 5 hours. This process results in the production of tetramethyldisilylazacyclopentane adducts, which can often be purified by vacuum distillation. The protected amines can be efficiently recovered by treating the Stabase adducts with methanol and a catalytic amount of p-toluenesulfonic acid monohydrate in ether. This method offers a balance of stability and ease of removal, making it an attractive choice for protecting primary amines.

Exact Mass

232.17900

Hazard Statements

F: Flammable;C: Corrosive;

Packaging

10 g; 100 g;

Safety Description

16-26-36/37/39-45

WGK Germany

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