(4-Bromophenylethynyl)trimethylsilane

Base Information

• Chemical Name: (4-Bromophenylethynyl)trimethylsilane
• CAS No.: 16116-78-2
• Molecular Formula: C11H13BrSi
• Molecular Weight: 253.214
• Hs Code.: 2931900090
• European Community (EC) Number: 835-531-4
• DSSTox Substance ID: DTXSID30401021
• Nikkaji Number: J832.815C
• Wikidata: Q82204087
• Mol file: 16116-78-2.mol

Synonyms:16116-78-2;(4-Bromophenylethynyl)trimethylsilane;((4-Bromophenyl)ethynyl)trimethylsilane;2-(4-bromophenyl)ethynyl-trimethylsilane;C11H13BrSi;BENZENE, 1-BROMO-4-[2-(TRIMETHYLSILYL)ETHYNYL]-;MFCD01863556;[(4-bromophenyl)ethynyl]trimethylsilane;2-(4-bromophenyl)ethynyl-trimethyl-silane;(4-bromo-phenylethynyl)-trimethyl-silane;[(4-bromophenyl)ethynyl](trimethyl)silane;[2-(4-BROMOPHENYL)ETHYNYL]TRIMETHYLSILANE;SCHEMBL613688;AMY1241;DTXSID30401021;RNMSGCJGNJYDNS-UHFFFAOYSA-N;p-bromophenylethynyl trimethylsilane;4-trimethylsilylethynyl bromo benzene;AKOS015913496;AB10391;DS-5170;(4-bromo-phenylethynyl)trimethyl silane;1-Bromo-4-(trimethysilylethynyl)benzene;SY083775;(4-Bromophenylethynyl)trimethylsilane, 98%;B6028;CS-0041418;FT-0743070;1-Bromo-4-[2-(trimethylsilyl)ethynyl]benzene;1-(trimethylsilyl)-2-(4-bromophenyl)acetylene;J-009794

Chemical Property of (4-Bromophenylethynyl)trimethylsilane

Chemical Property:

• Vapor Pressure: 0.041mmHg at 25°C
• Melting Point: 61-63 °C (lit.)
• Refractive Index: 1.543
• Boiling Point: 247.1 °C at 760 mmHg
• Flash Point: 144 °C
• PSA: 0.00000
• Density: 1.23 g/cm³
• 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: 220

Purity/Quality:

98%, ^*data from raw suppliers

(4-Bromophenylethynyl)trimethylsilane ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C#CC1=CC=C(C=C1)Br
• Uses: (4-Bromophenylethynyl)trimethylsilane may be used to synthesize:1-bromo-4-ethynylbenzene4-(4-bromophenyl)-3-butyn-2-one4-ethynyl-4′-tert-butylbiphenyl1,4-bis[2-(4-bromophenyl)ethynyl]-2,5-dihexylbenzene

Technology Process of (4-Bromophenylethynyl)trimethylsilane

There total 20 articles about (4-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%

1,4-bromoiodobenzene (589-87-7) + trimethylsilylacetylene (1066-54-2) → (4-bromophenyl)(trimethylsilyl)acetylene (16116-78-2)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 100 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.joc.5b00416

Reference yield: 99.0%

4-bromo-1-ethynylbenzene (766-96-1) + (trifluoromethyl)trimethylsilane (81290-20-2) → (4-bromophenyl)(trimethylsilyl)acetylene (16116-78-2)

Guidance literature:

With sodium hydride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; In neat (no solvent); at 31 - 33 ℃; for 0.25h;

DOI:10.1039/c4ra08727e

Reference yield: 91.0%

1,4-bromoiodobenzene (589-87-7) + trimethylsilylacetylene (1066-54-2) → (4-bromophenyl)(trimethylsilyl)acetylene (16116-78-2) + 1,4-Bis(trimethylsilylethynyl)benzene (17938-13-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1021/ja0031220

upstream raw materials:

chloro-trimethyl-silane

4-bromo-1-ethynylbenzene

1,4-bromoiodobenzene

trimethylsilylacetylene

Downstream raw materials:

4-deuterio-(trimethylsilylethynyl)benzene

4-bromo-1-ethynylbenzene

tris(4-iodophenyl)-(4'-(trimethylsilylethynyl)phenyl)-silane

((4-((trimethylsilyl)ethynyl)phenyl)-ethynyl)triisopropylsilane

Refernces

• 1、 Asao, Naoki,Tomeba, Hisamitsu,Yamamoto, Yoshinori. "Synthesis of organosilicon polymers by using the Lewis-acid-catalyzed trans-allylsilylation of alkynes". . p. 27 - 30. Retrieved 2005.
• 2、 Xu, Shaoyi,Adamski, Michael,Killer, Miho,Schibli, Eric M.,Frisken, Barbara J.,Holdcroft, Steven. "Sulfo-Phenylated Polyphenylenes Containing Sterically Hindered Pyridines". . p. 2548 - 2559. Retrieved 2019.
• 3、 Makhoul, Rim,Gluyas, Josef B. G.,Vincent, Kevin B.,Sahnoune, Hiba,Halet, Jean-Fran?ois,Low, Paul J.,Hamon, Jean-René,Lapinte, Claude. "Redox Properties of Ferrocenyl Ene-diynyl-Bridged Cp?(dppe)M-C≡C-1,4-(C6H4) Complexes". . p. 4156 - 4171. Retrieved 2018.
• 4、 Wang, Fei,Kaafarani, Bilal R.,Neckers, Douglas C.. "Synthesis of silicon-containing unsaturated polymers by hydrosilylation reaction. Photophysical studies". . p. 8225 - 8230. Retrieved 2003.
• 5、 Sattler, Lars E.,Hilt, Gerhard. "Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles". supporting information. p. 605 - 608. Retrieved 2020/12/07.
• 6、 Kimaru, Natsuki,Komatsuki, Keiichi,Saito, Kodai,Yamada, Tohru. "Decarboxylation-triggered homo-Nazarov cyclization of cyclic enol carbonates catalyzed by rhenium complex". supporting information. p. 6133 - 6136. Retrieved 2021/06/30.