1,2-Bis(Dimethylaminodimethylsilyl)Ethane

Catalog Number	ACM91166506
CAS Number	91166-50-6
Structure
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	12-Bis(Dimethylaminodimethylsilyl)Ethane serves as a valuable reagent for safeguarding primary amines particularly those with lower pKa values such as substituted anilines by converting them into tetramethyldisilylazacyclopentane or Stabase adducts It is especially effective for protecting primary aromatic amines with pKa values between 10 and 11 This process involves heating equimolar amounts of 12-Bis(Dimethylaminodimethylsilyl)Ethane and anilines with a catalytic amount of zinc iodide under a nitrogen atmosphere at 140°C for five hours The resulting compounds can often be purified via vacuum distillation Reversion of the Stabase adducts back to their corresponding primary amines is easily accomplished in ether with methanol and a minimal amount of p-toluenesulfonic acid monohydrate The Stabase adduct stands out as an attractive protective group due to its straightforward synthesis stability in basic conditions and easy removal
Exact Mass	232.17900
Packaging	10 g; 100 g;
WGK Germany	3

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