1,2-Bis(Dimethylaminodimethylsilyl)Ethane

• CAS: 91166-50-6
• Catalog Number: ACM91166506
• Category: Other Organosilicon
• Molecular Weight: 232.52 g/mol
• Molecular Formula: C10H28N2Si2
• 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
• 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
• 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
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Packaging: 10 g; 100 g
• Packing Group: II
• Safety Description: 16-26-36/37/39-45
• WGK Germany: 3

Custom Q&A

What is the molecular formula of 1,2-Bis(dimethylaminodimethylsilyl)ethane?

The molecular formula is C10H28N2Si2.

What are the synonyms for 1,2-Bis(dimethylaminodimethylsilyl)ethane?

The synonyms are 91166-50-6, Bis(dimethylaminodimethylsilyl)ethane, 1,1'-(Ethane-1,2-diyl)bis(N,N,1,1-tetramethylsilanamine), and N-[2-[dimethylamino(dimethyl)silyl]ethyl-dimethylsilyl]-N-methylmethanamine.

What is the molecular weight of 1,2-Bis(dimethylaminodimethylsilyl)ethane?

The molecular weight is 232.51 g/mol.

When was 1,2-Bis(dimethylaminodimethylsilyl)ethane created and modified in PubChem?

It was created on September 13, 2005, and last modified on November 25, 2023.

What is the IUPAC name of 1,2-Bis(dimethylaminodimethylsilyl)ethane?

The IUPAC name is N-[2-[dimethylamino(dimethyl)silyl]ethyl-dimethylsilyl]-N-methylmethanamine.

What is the InChI of 1,2-Bis(dimethylaminodimethylsilyl)ethane?

The InChI is InChI=1S/C10H28N2Si2/c1-11(2)13(5,6)9-10-14(7,8)12(3)4/h9-10H2,1-8H3.

What is the InChIKey of 1,2-Bis(dimethylaminodimethylsilyl)ethane?

The InChIKey is MRAAXSSHMOFDJR-UHFFFAOYSA-N.

What is the canonical SMILES of 1,2-Bis(dimethylaminodimethylsilyl)ethane?

The canonical SMILES is CN(C)[Si](C)(C)CC[Si](C)(C)N(C)C.

What is the CAS number of 1,2-Bis(dimethylaminodimethylsilyl)ethane?

The CAS number is 91166-50-6.

What is the European Community (EC) number of 1,2-Bis(dimethylaminodimethylsilyl)ethane?

The European Community (EC) number is 627-524-8.