Silane, [(5-bromo-3-pentynyl)oxy](1,1-dimethylethyl)diphenyl-

Base Information

• Chemical Name: Silane, [(5-bromo-3-pentynyl)oxy](1,1-dimethylethyl)diphenyl-
• CAS No.: 88158-71-8
• Molecular Formula: C21H25BrOSi
• Molecular Weight: 401.418
• DSSTox Substance ID: DTXSID80451091
• Nikkaji Number: J940.138E
• Wikidata: Q82270961
• Mol file: 88158-71-8.mol

Synonyms:88158-71-8;Silane, [(5-bromo-3-pentynyl)oxy](1,1-dimethylethyl)diphenyl-;DTXSID80451091;1-Bromo-5-(tert-butyldiphenylsiloxy)-2-pentyne

Chemical Property of Silane, [(5-bromo-3-pentynyl)oxy](1,1-dimethylethyl)diphenyl-

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 400.08580
• Heavy Atom Count: 24
• Complexity: 412

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C1=CC=CC=C1)(C2=CC=CC=C2)OCCC#CCBr

Technology Process of Silane, [(5-bromo-3-pentynyl)oxy](1,1-dimethylethyl)diphenyl-

There total 7 articles about Silane, [(5-bromo-3-pentynyl)oxy](1,1-dimethylethyl)diphenyl- 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: 99.0%

5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-yn-1-ol (88159-03-9) → ((5-bromopent-3-yn-1-yl)oxy)(tert-butyl)diphenylsilane (88158-71-8)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(97)10607-4

Reference yield: 78.0%

carbon tetrabromide (558-13-4) + 5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-yn-1-ol (88159-03-9) → ((5-bromopent-3-yn-1-yl)oxy)(tert-butyl)diphenylsilane (88158-71-8)

Guidance literature:

With triphenylphosphine; at 0 - 20 ℃; for 4h;

DOI:10.1002/chem.202002138

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → ((5-bromopent-3-yn-1-yl)oxy)(tert-butyl)diphenylsilane (88158-71-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 2.5 h / 0 °C / Sealed tube; Inert atmosphere

2.1: n-butyllithium / diethyl ether; hexane / 0.25 h / -78 °C / Inert atmosphere

2.2: 7 h / Sealed tube; Inert atmosphere

3.1: triethylamine; methanesulfonyl chloride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

3.2: 20 °C / 760.05 Torr / Inert atmosphere

With 1H-imidazole; n-butyllithium; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide;

DOI:10.1021/acs.orglett.7b00879

upstream raw materials:

formaldehyd

4-(tert-butyldiphenylsilyloxy)-1-butyne

5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-yn-1-ol

5-(tetrahydropyran-2-yloxy)-3-pentyn-1-ol

Downstream raw materials:

C₁₂H₁₅NO

(Z)-3-benzyl-5-(3-hydroxypropylidene)oxazolidin-2-one

3-benzyl-6-(2-hydroxy-ethyl)-3,4-dihydro-[1,3]oxazin-2-one

N-benzyl-5-(tert-butyldiphenylsilyloxy)pent-2-yn-1-amine