(4-Ethylphenylethynyl)trimethylsilane

Base Information

• Chemical Name: (4-Ethylphenylethynyl)trimethylsilane
• CAS No.: 393857-27-7
• Molecular Formula: C₁₃H₁₈Si
• Molecular Weight: 202.371
• DSSTox Substance ID: DTXSID80461594
• Nikkaji Number: J1.795.231E
• Wikidata: Q82285962
• Mol file: 393857-27-7.mol

Synonyms:(4-Ethylphenylethynyl)trimethylsilane;393857-27-7;2-(4-ethylphenyl)ethynyl-trimethylsilane;(4-Ethyl-phenylethynyl)-trimethyl-silane;Silane, [(4-ethylphenyl)ethynyl]trimethyl-;[2-(4-ETHYLPHENYL)ETHYNYL]TRIMETHYLSILANE;DTXSID80461594;NADBKXSXWBPNBB-UHFFFAOYSA-N;MFCD05664231;AKOS015913616;((4-Ethylphenyl)ethynyl)trimethylsilane;4-ethyl-1-trimethylsilyl ethynylbenzene;(4-Ethylphenylethynyl)trimethylsilane, 97%

Chemical Property of (4-Ethylphenylethynyl)trimethylsilane

Chemical Property:

• Vapor Pressure: 0.0589mmHg at 25°C
• Refractive Index: n20/D 1.5270(lit.)
• Boiling Point: 72 °C0.1 mm Hg(lit.)
• Flash Point: 228 °F
• PSA: 0.00000
• Density: 0.881 g/mL at 25 °C(lit.)
• LogP: 3.47790
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 202.117777109
• Heavy Atom Count: 14
• Complexity: 227

Purity/Quality:

99%min ^*data from raw suppliers

(4-Ethyl-phenylethynyl)-trimethyl-silane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC1=CC=C(C=C1)C#C[Si](C)(C)C

Technology Process of (4-Ethylphenylethynyl)trimethylsilane

There total 3 articles about (4-Ethylphenylethynyl)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: 99.0%

4-ethyl-1-iodobenzene (25309-64-2) + trimethylsilylacetylene (1066-54-2) → (2-(4-ethylphenyl)ethynyl)trimethylsilane (393857-27-7)

Guidance literature:

With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0040-4039(02)01538-1

Reference yield: 95.0%

1-bromo-4-ethylbenzene (1585-07-5) + trimethylsilylacetylene (1066-54-2) → (2-(4-ethylphenyl)ethynyl)trimethylsilane (393857-27-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In acetonitrile; at 120 ℃; for 0.0833333h; Microwave irradiation; Sealed tube; Inert atmosphere;

DOI:10.1016/j.tetlet.2016.01.088

Reference yield:

[(4-ethenylphenyl)ethynyl]trimethylsilane (135005-24-2) → (2-(4-ethylphenyl)ethynyl)trimethylsilane (393857-27-7)

Guidance literature:

With {Rh₂(1,5-cyclooctadiene)2[2,6-(Ph₂PCH₂)2C₆H₃O]}(ClO₄); hydrogen; In tetrahydrofuran; at 20 ℃; for 20h; under 760.051 Torr; chemoselective reaction;

DOI:10.1021/om100067r

upstream raw materials:

4-ethyl-1-iodobenzene

trimethylsilylacetylene

1-bromo-4-ethylbenzene

[(4-ethenylphenyl)ethynyl]trimethylsilane

Downstream raw materials:

1-ethyl-4-(phenylethynyl)benzene

4-ethylacetophenone

1-ethyl-4-ethynylbenzene

Refernces

• 1、 Buendia, Julien,Darses, Benjamin,Dauban, Philippe. "Tandem catalytic C(sp3)-H amination/sila-sonogashira-hagihara coupling reactions with iodine reagents". supporting information. p. 5697 - 5701. Retrieved 2015/06/16.
• 2、 Xu, Caixia,Du, Weiyuan,Zeng, Yi,Dai, Bin,Guo, Hao. "Reactivity switch enabled by counterion: Highly chemoselective dimerization and hydration of terminal alkynes". supporting information. p. 948 - 951. Retrieved 2014/03/21.