3-Bromo-1-(triethylsilyl)-1-propyne

Base Information

• Chemical Name: 3-Bromo-1-(triethylsilyl)-1-propyne
• CAS No.: 220913-60-0
• Molecular Formula: C9H17BrSi
• Molecular Weight: 233.223
• DSSTox Substance ID: DTXSID80373764
• Nikkaji Number: J1.083.909B
• Wikidata: Q82162093
• Mol file: 220913-60-0.mol

Synonyms:3-Bromo-1-(triethylsilyl)-1-propyne;220913-60-0;(3-bromoprop-1-yn-1-yl)triethylsilane;AC1MBVAV;SCHEMBL2830004;DTXSID80373764;(3-bromoprop-1-ynyl)triethylsilane;1-(Triethylsilyl)-3-bromo-1-propyne;3-BROMO-1-TRIETHYLSILYL-1-PROPYNE

Chemical Property of 3-Bromo-1-(triethylsilyl)-1-propyne

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 232.02829
• Heavy Atom Count: 11
• Complexity: 151

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC[Si](CC)(CC)C#CCBr

Technology Process of 3-Bromo-1-(triethylsilyl)-1-propyne

There total 1 articles about 3-Bromo-1-(triethylsilyl)-1-propyne 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: 37.0%

n-butyllithium (109-72-8,29786-93-4) + triethylsilyl chloride (994-30-9) + propargyl bromide (106-96-7) → triethyl(hept-1-yn-1-yl)silane (1047660-72-9) + (3-bromoprop-1-yn-1-yl)triethylsilane (220913-60-0)

Guidance literature:

n-butyllithium; propargyl bromide; In tetrahydrofuran; at -78 ℃;

triethylsilyl chloride; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/j.bmc.2017.05.038

Reference yield: 93.0%

(4S,5R,Z)-4-((4-methoxybenzyl)oxy)-5-methylnona-1,6-dien-5-ol + (3-bromoprop-1-yn-1-yl)triethylsilane (220913-60-0) → triethyl(3-(((4S,5R,6E)-4-((4-methoxybenzyl)oxy)-5-methylnona-1,6-dien-5-yl)oxy)prop-1-yn-1-yl)silane

Guidance literature:

(4S,5R,Z)-4-((4-methoxybenzyl)oxy)-5-methylnona-1,6-dien-5-ol; With sodium hydride; In tetrahydrofuran; water; mineral oil; at 40 ℃; for 4h; Schlenk technique; Inert atmosphere;

(3-bromoprop-1-yn-1-yl)triethylsilane; In tetrahydrofuran; water; mineral oil; at 40 ℃; for 20.5h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.7b01744

Reference yield: 91.0%

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) + (3-bromoprop-1-yn-1-yl)triethylsilane (220913-60-0) → tert-butyl (2S)-2-(benzhydrylidene-amino)-5-triethylsilyl-4-pentynoate (612825-71-5)

Guidance literature:

With potassium hydroxide; O⁽⁹⁾-allyl-N⁽¹⁾-2',3',4'-trifluorobenzylhydrocinchonidinium bromide; In chloroform; water; toluene; at -30 ℃; for 20h;

DOI:10.1021/ja909870g

upstream raw materials:

n-butyllithium

triethylsilyl chloride

propargyl bromide

Downstream raw materials:

tert-butyl (2S)-2-(benzhydrylidene-amino)-5-triethylsilyl-4-pentynoate

tert-butyl (2S)-2-benzyloxycarbonylamino-5-triethylsilyl-4-pentynoate

C₂₆H₄₄OSSi₂