Trimethyl[4-(phenylethynyl)phenyl]silane

Base Information

• Chemical Name: Trimethyl[4-(phenylethynyl)phenyl]silane
• CAS No.: 136459-72-8
• Molecular Formula: C17H18Si
• Molecular Weight: 250.415
• Mol file: 136459-72-8.mol

Synonyms:Trimethyl[4-(phenylethynyl)phenyl]silane;1-(2-Phenylethynyl)-4-(trimethylsilyl)benzene;

Chemical Property of Trimethyl[4-(phenylethynyl)phenyl]silane

Chemical Property:

• Melting Point: 39 °C
• Refractive Index: 1.562
• Boiling Point: 344.2 °C at 760 mmHg
• Flash Point: 148.1 °C
• PSA: 0.00000
• Density: 0.99 g/cm³
• LogP: 3.63160
• Solubility.: soluble in Toluene

Purity/Quality:

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

4-(Trimethylsilyl)diphenylacetylene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Use Description: Trimethyl[4-(phenylethynyl)phenyl]silane is a versatile chemical compound with applications in various fields. In the realm of organic synthesis and materials science, it serves as a crucial reagent and building block for the creation of complex organic molecules and polymers, enabling the development of innovative materials with unique properties. Its role is pivotal in the production of specialty chemicals and advanced materials, contributing to advancements in materials technology. Additionally, in the field of chemical research and analytical chemistry, this compound can be employed as a reference compound for the study of silanes and their reactivity, aiding in the advancement of synthetic methodologies and chemical understanding. Furthermore, in the electronics and semiconductor industry, it is used as a precursor in the fabrication of organic electronic devices and thin films, playing a crucial role in the development of cutting-edge technology. Its multifaceted utility underscores its significance in materials science, chemical research, and electronics, where it plays a crucial role in material innovation, chemical synthesis, and technological advancement.

Technology Process of Trimethyl[4-(phenylethynyl)phenyl]silane

There total 9 articles about Trimethyl[4-(phenylethynyl)phenyl]silane 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: 91.0%

1-bromo-4-(trimethylsilyl)benzene (6999-03-7) + diethyl(phenylethynyl)aluminum (5075-59-2) → 1-phenyl-2-acetylene (136459-72-8)

Guidance literature:

With bis(triphenylphosphine)nickel(II) chloride; In 1,2-dimethoxyethane; at 80 ℃; for 4h; Inert atmosphere;

DOI:10.1039/c1cc14206b

Reference yield: 81.0%

1-Bromo-2-phenylacetylene (932-87-6) + [4-(trimethylsilyl)phenyl]magnesium bromide (17878-43-2) → 1-phenyl-2-acetylene (136459-72-8)

Guidance literature:

With Tri(p-tolyl)phosphine; nickel dichloride; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.cclet.2014.04.019

Reference yield: 73.0%

p-(trimethylsilyl) phenylacetylene (16116-92-0) + N,N,N-trimethylbenzeneaminium trifluoromethanesulfonate → 1-phenyl-2-acetylene (136459-72-8)

Guidance literature:

With SIPr-PdCl₂-Py; sodium t-butanolate; In tetrahydrofuran; at 45 ℃; for 4h; Inert atmosphere;

DOI:10.1021/acscatal.9b00218

upstream raw materials:

chloro-trimethyl-silane

1-bromo-4-phenylethynylbenzene

1,4-bromoiodobenzene

phenylacetylene

Refernces

• 1、 Li, Qing-Han,Ding, Yong,Yang, Xue-Jun. "Nickel-catalyzed cross-coupling reaction of alkynyl bromides with Grignard reagents". . p. 1296 - 1300. Retrieved 2014.
• 2、 Chen, Qianwei,Gao, Fengchen,Tang, Huiling,Yao, Miao,Zhao, Qian,Shi, Yanhui,Dang, Yanfeng,Cao, Changsheng. "Sonogashira Cross-Coupling of Aryltrimethylammonium Salts". . p. 3730 - 3736. Retrieved 2019/04/13.