(4-FLUOROPHENYLETHYNYL)TRIMETHYLSILANE

Base Information

• Chemical Name: (4-FLUOROPHENYLETHYNYL)TRIMETHYLSILANE
• CAS No.: 130995-12-9
• Molecular Formula: C11H13FSi
• Molecular Weight: 192.308
• European Community (EC) Number: 623-358-5
• DSSTox Substance ID: DTXSID00408345
• Nikkaji Number: J976.001F
• Mol file: 130995-12-9.mol

Synonyms:(2-(4-fluorophenyl)ethynyl)trimethylsilane;4-(trimethylsilylethynyl)fluorobenzene;[(4-fluorophenyl)ethynyl]trimethylsilane;1-fluoro-4-[(2-trimethylsilyl)ethynyl]benzene;1-(4-fluorophenyl)-2-trimethylsilylacetylene;

Chemical Property of (4-FLUOROPHENYLETHYNYL)TRIMETHYLSILANE

Chemical Property:

• Vapor Pressure: 0.449mmHg at 25°C
• Refractive Index: n20/D 1.5090(lit.)
• Boiling Point: 40 °C0.1 mm Hg(lit.)
• Flash Point: 195 °F
• PSA: 0.00000
• Density: 0.948 g/mL at 25 °C(lit.)
• LogP: 3.05460
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 192.07705511
• Heavy Atom Count: 13
• Complexity: 220

Purity/Quality:

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

(4-Fluorophenylethynyl)trimethylsilane 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C#CC1=CC=C(C=C1)F

Technology Process of (4-FLUOROPHENYLETHYNYL)TRIMETHYLSILANE

There total 7 articles about (4-FLUOROPHENYLETHYNYL)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%

4-fluoro-1-iodobenzene (352-34-1) + trimethylsilylacetylene (1066-54-2) → 1-(4-fluorophenyl)-2-trimethylsilylacetylene (130995-12-9)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 50 ℃; for 6h; Inert atmosphere;

DOI:10.1021/ol301474g

Reference yield: 97.0%

1-Bromo-4-fluorobenzene (460-00-4) + trimethylsilylacetylene (1066-54-2) → 1-(4-fluorophenyl)-2-trimethylsilylacetylene (130995-12-9)

Guidance literature:

With copper(l) iodide; diisopropylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; 1.) r.t., 16 h, 2.) reflux, 3 h;

DOI:10.1021/jo00076a019

Reference yield: 69.0%

1-ethynyl-4-fluorobenzene (766-98-3) + chloro-trimethyl-silane (75-77-4) → 1-(4-fluorophenyl)-2-trimethylsilylacetylene (130995-12-9)

Guidance literature:

1-ethynyl-4-fluorobenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

chloro-trimethyl-silane; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/anie.202000473

upstream raw materials:

1-Bromo-4-fluorobenzene

trimethylsilylacetylene

4-fluoro-1-iodobenzene

Tris(trimethylsilyl)methane

Downstream raw materials:

(E)-2-(4-fluorophenylethenyl)trimethylsilane

methyl 3-(4-fluorophenyl)propiolate

ethyl 5-(4-fluorophenyl)-3-(p-tolyl)thiophene-2-carboxylate

4,4'-(but-3-en-1-yne-1,3-diyl)bis(fluorobenzene)

Refernces

• 1、 Lappert, Michael F.,Layh, Marcus. "A new one-pot arylacetylene synthesis: 4-RC6H4C-≡C(TMS) from 4- RC6H4CN and LiC(TMS)3(THF)2 via Li[N(TMS)C(C6H4R-4)C(TMS)2](THF) (TMS = SiMe3, R = H, F, Br, OMe or Bu(t))". . p. 4745 - 4748. Retrieved 1998.
• 2、 Klukas, Fabian,Perkampus, J?rg,Urselmann, Dominik,Müller, Thomas J. J.. "Pseudo five-component synthesis of 3-(hetero)arylmethyl-2,5-di(hetero)-aryl-substituted thiophenes via sonogashira-glaser cyclization sequence". . p. 3415 - 3422. Retrieved 2014.
• 3、 Sugimoto, Kenji,Kosuge, Shuto,Sugita, Takae,Miura, Yuka,Tsuge, Kiyoshi,Matsuya, Yuji. "Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization". supporting information. p. 3981 - 3985. Retrieved 2021/05/26.
• 4、 Varga, Bálint,Tóth, Balázs L.,Béke, Ferenc,Csenki, János T.,Kotschy, András,Novák, Zoltán. "Synthesis and Photochemical Application of Hydrofluoroolefin (HFO) Based Fluoroalkyl Building Block". supporting information. p. 4925 - 4929. Retrieved 2021/07/01.