(3-Bromophenylethynyl)trimethylsilane

Base Information

• Chemical Name: (3-Bromophenylethynyl)trimethylsilane
• CAS No.: 3989-13-7
• Molecular Formula: C11H13 Br Si
• Molecular Weight: 253.214
• European Community (EC) Number: 878-379-4
• DSSTox Substance ID: DTXSID80394999
• Nikkaji Number: J1.821.634E
• Wikidata: Q82194750
• Mol file: 3989-13-7.mol

Synonyms:3989-13-7;(3-Bromophenylethynyl)trimethylsilane;((3-bromophenyl)ethynyl)trimethylsilane;2-(3-bromophenyl)ethynyl-trimethylsilane;[2-(3-BROMOPHENYL)ETHYNYL]TRIMETHYLSILANE;[(3-Bromophenyl)ethynyl]trimethylsilane;[(3-bromophenyl)ethynyl](trimethyl)silane;2-(3-bromophenyl)ethynyl-trimethyl-silane;SCHEMBL2795902;DTXSID80394999;BXXMHQYHYOTTPM-UHFFFAOYSA-N;3-bromophenyltrimethylsilylacetylene;1-bromo-3trimethylsilylethynylbenzene;3-(trimethylsilylethynyl)bromobenzene;MFCD01863664;1-bromo-3-trimethylsilylethynylbenzene;AKOS015913287;AB10401;1-(Trimethylsilylethynyl)-3-bromobenzene;BS-16733;(3-Bromophenylethynyl)trimethylsilane, 97%;B5199;CS-0163092;1-Bromo-3-[2-(trimethylsilyl)ethynyl]benzene;D80250

Chemical Property of (3-Bromophenylethynyl)trimethylsilane

Chemical Property:

• Vapor Pressure: 0.0262mmHg at 25°C
• Refractive Index: n20/D 1.555(lit.)
• Boiling Point: 80 °C0.2 mm Hg(lit.)
• Flash Point: >230 °F
• PSA: 0.00000
• Density: 1.189 g/mL at 25 °C(lit.)
• LogP: 3.67800
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 251.99699
• Heavy Atom Count: 13
• Complexity: 228

Purity/Quality:

99% ^*data from raw suppliers

(3-Bromophenylethynyl)trimethylsilane 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C#CC1=CC(=CC=C1)Br
• Uses: (3-Bromophenylethynyl)trimethylsilane may be used in the preparation of 4-(3-bromophenyl)-3-butyn-2-one.

Technology Process of (3-Bromophenylethynyl)trimethylsilane

There total 5 articles about (3-Bromophenylethynyl)trimethylsilane 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: 100.0%

1-Bromo-3-iodobenzene (591-18-4) + trimethylsilylacetylene (1066-54-2) → 2-(3-bromophenyl)ethynyltrimethylsilane (3989-13-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; trimethylamine; for 0.5h; Inert atmosphere; Schlenk technique; Reflux;

DOI:10.1021/acs.orglett.7b02452

Reference yield: 47.0%

1,3-dibromobenzene (108-36-1) + trimethylsilylacetylene (1066-54-2) → 2-(3-bromophenyl)ethynyltrimethylsilane (3989-13-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; TEA; In tetrahydrofuran; at 75 ℃; for 12h;

DOI:10.1016/S0040-4020(03)00246-1

Reference yield:

1,3-dibromobenzene (108-36-1) + trimethylsilylacetylene (1066-54-2) + 2,3-dibromobenzene (583-53-9) → 2-(3-bromophenyl)ethynyltrimethylsilane (3989-13-7)

Guidance literature:

With triethylamine; palladium; tetrakis(triphenylphosphine)palladium ⁽⁰⁾; In nitrogen; toluene;

upstream raw materials:

chloro-trimethyl-silane

3-bromophenylacetylene

1-Bromo-3-iodobenzene

trimethylsilylacetylene

Downstream raw materials:

3-(3-bromophenyl)-2-propyn-1-ol

ethyl m-(bromophenyl)propiolate

Refernces

• 1、 Burnett, James C.,Lim, Chaemin,Peyser, Brian D.,Samankumara, Lalith P.,Kovaliov, Marina,Colombo, Raffaele,Bulfer, Stacie L.,LaPorte, Matthew G.,Hermone, Ann R.,McGrath, Connor F.,Arkin, Michelle R.,Gussio, Rick,Huryn, Donna M.,Wipf, Peter. "A threonine turnstile defines a dynamic amphiphilic binding motif in the AAA ATPase p97 allosteric binding site". . p. 4096 - 4114. Retrieved 2017.
• 2、 -. "COMPOUND FOR ORGANIC OPTOELECTRONIC DEVICE, ORGANIC OPTOELECTRONIC DEVICE AND DISPLAY APPARATUS". Paragraph 0159; 0160. . Retrieved 2018/12/11.
• 3、 Kasten, Kevin,Slawin, Alexandra M. Z.,Smith, Andrew D.. "Enantioselective synthesis of β-fluoro-β-aryl-α-aminopentenamides by organocatalytic [2,3]-sigmatropic rearrangement". supporting information. p. 5182 - 5185. Retrieved 2017/11/06.