1,2-Bis[(dimethylamino)dimethylsilyl]ethane

Base Information

• Chemical Name: 1,2-Bis[(dimethylamino)dimethylsilyl]ethane
• CAS No.: 91166-50-6
• Molecular Formula: C10H28N2Si2
• Molecular Weight: 232.51
• Hs Code.: 29319019
• European Community (EC) Number: 627-524-8
• DSSTox Substance ID: DTXSID40400500
• Nikkaji Number: J364.725K
• Wikidata: Q82203505
• Mol file: 91166-50-6.mol

Synonyms:91166-50-6;1,2-Bis[(dimethylamino)dimethylsilyl]ethane;Bis(dimethylaminodimethylsilyl)ethane;1,1'-(Ethane-1,2-diyl)bis(N,N,1,1-tetramethylsilanamine);N-[2-[dimethylamino(dimethyl)silyl]ethyl-dimethylsilyl]-N-methylmethanamine;1,2-bis(dimethylaminodimethylsilyl)ethane;1,1'-Ethylenebis(N,N,1,1-tetramethylsilanamine);SCHEMBL1345170;DTXSID40400500;MFCD00010649;AKOS015895013;1,2-Bis[dimethyl(dimethylamino)silyl]ethane;B1773;FT-0642190;1,2-Bis(Dimethylaminodimethylsilyl)Ethane,96%;1,2-bis[ (dimethylamino )dimethylsilyl]ethane;D88858;S01610;1,2-Bis[(dimethylamino)dimethylsilyl]ethane, 96%;1,1'-(1,2-Ethanediyl)Bis[N,N,1,1-Tetramethyl-Silanamine

Chemical Property of 1,2-Bis[(dimethylamino)dimethylsilyl]ethane

Chemical Property:

• Vapor Pressure: 0.157mmHg at 25°C
• Refractive Index: n20/D 1.446(lit.)
• Boiling Point: 221.7 °C at 760 mmHg
• PKA: 10.31±0.70(Predicted)
• Flash Point: 87.9 °C
• PSA: 6.48000
• Density: 0.831g/cm³
• LogP: 2.51980
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 232.17910197
• Heavy Atom Count: 14
• Complexity: 157

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,1''-(1,2-Ethanediyl)bis[N,N,1,1-tetramethylsilanamine] ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F; C
• Hazard Codes: F,C
• Statements: 11-34
• Safety Statements: 16-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)[Si](C)(C)CC[Si](C)(C)N(C)C
• 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).

Technology Process of 1,2-Bis[(dimethylamino)dimethylsilyl]ethane

There total 1 articles about 1,2-Bis[(dimethylamino)dimethylsilyl]ethane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

1,2-bis-(chlorodimethylsilyl)ethane (13528-93-3) + dimethyl amine (124-40-3) → 1,1'-(1,2-ethanediyl)bis (91166-50-6)

Guidance literature:

In diethyl ether; at 0 ℃; for 5h;

DOI:10.1016/S0040-4039(01)80126-X

Reference yield: 94.0%

1,1'-(1,2-ethanediyl)bis (91166-50-6) + m-Bromoaniline (591-19-5) → 1-(3-bromophenyl)-2,2,5,5-tetramethyl-1,2,5-azadisilolidine (91166-51-7)

Guidance literature:

With zinc(II) iodide; at 140 ℃; for 5h;

DOI:10.1016/S0040-4039(01)80126-X

Reference yield: 94.0%

1,1'-(1,2-ethanediyl)bis (91166-50-6) + p-toluidine (106-49-0,12221-03-3) → 2,2,5,5-Tetramethyl-1-p-tolyl-[1,2,5]azadisilolidine (78605-24-0)

Guidance literature:

With zinc(II) iodide; for 5h; 1.) 70 deg C, 1h; 2.) 140 deg C, 4 h;

DOI:10.1016/S0040-4039(01)80126-X

upstream raw materials:

1,2-bis-(chlorodimethylsilyl)ethane

dimethyl amine

Downstream raw materials:

2,2,5,5-Tetramethyl-1-p-tolyl-[1,2,5]azadisilolidine

(1-phenyl-2,2,5,5-tetramethyl)-1-aza-2,5-disilacyclopentane

2,2,5,5-Tetramethyl-1-m-tolyl-[1,2,5]azadisilolidine

1-(3-bromophenyl)-2,2,5,5-tetramethyl-1,2,5-azadisilolidine

Refernces