1,2-Bis[(Dimethylamino)Dimethylsilyl]Ethane [Protecting Reagent For Aromatic Primary Amines]

Catalog Number	ACM91166506-2
CAS Number	91166-50-6
Structure
Synonyms	1,1'-Ethylenebis(N,N,1,1-Tetramethylsilanamine)
Molecular Weight	232.52 g/mol
Molecular Formula	C10H28N2Si2
Boiling Point	103 °C(13 mmHg)
Flash Point	13 °C
Purity	>93%
Appearance	Colorless to Almost colorless clear liquid
Application	12-Bis[(Dimethylamino)Dimethylsilyl]Ethane serves as an effective protecting reagent for aromatic primary amines such as substituted anilines which have pKa values in the range of 10–11 This compound is specifically utilized for the preparation of Stabase derivatives offering practical protection for primary aromatic amines The protection process involves heating equal quantities of the reagent and the target amines at 140°C with a catalytic amount of zinc iodide under a gentle nitrogen flow for a duration of five hours The resulting protected products are often amenable to purification through vacuum distillation Furthermore the removal of the protective Stabase adduct to regenerate the primary amines can be efficiently achieved in an ether solution using methanol and a small amount of p-toluenesulfonic acid monohydrate This Stabase adduct serves as a valuable protecting group due to its straightforward preparation stability in basic conditions and easy removal
Storage	Store under inert gas
MDL Number	MFCD00010649
Reaxys Registry Number	4366167
Specific Gravity	0.84