Silane, trimethyl(2-phenylethenyl)-, (Z)-

Base Information

• Chemical Name: Silane, trimethyl(2-phenylethenyl)-, (Z)-
• CAS No.: 19319-11-0
• Molecular Formula: C11H16 Si
• Molecular Weight: 176.334
• Nikkaji Number: J156.730F
• Mol file: 19319-11-0.mol

Synonyms:19319-11-0;Trimethyl[(Z)-2-phenylvinyl]silane;Silane, trimethyl(2-phenylethenyl)-, (Z)-;(Z)-beta-(Trimethylsilyl)styrene;Silane,trimethyl(2-phenylethenyl)-,(Z)-

Chemical Property of Silane, trimethyl(2-phenylethenyl)-, (Z)-

Chemical Property:

• Vapor Pressure: 0.231mmHg at 25°C
• Boiling Point: 214.1°C at 760 mmHg
• Flash Point: 68.7°C
• Density: 0.885g/cm³
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 176.102127045
• Heavy Atom Count: 12
• Complexity: 147

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C=CC1=CC=CC=C1
• Isomeric SMILES: C[Si](C)(C)/C=C\C1=CC=CC=C1

Technology Process of Silane, trimethyl(2-phenylethenyl)-, (Z)-

There total 32 articles about Silane, trimethyl(2-phenylethenyl)-, (Z)- 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: 97.0%

1-Phenyl-2-(trimethylsilyl)acetylene (2170-06-1) → (Z)-1-phenyl-2-(trimethylsilyl)ethylene (19319-11-0)

Guidance literature:

1-Phenyl-2-(trimethylsilyl)acetylene; With diisobutylaluminium hydride; In diethyl ether; hexane; at 20 ℃; for 50.1667h; Inert atmosphere;

With sulfuric acid; In diethyl ether; hexane; water; stereoselective reaction;

DOI:10.1016/j.tet.2009.10.077

Reference yield: 90.0%

1-(trimethylsilyl)-2-phenylethene (19372-00-0) → (Z)-1-phenyl-2-(trimethylsilyl)ethylene (19319-11-0)

Guidance literature:

With benzophenone; In cyclohexane; at 20 ℃; for 2h; Inert atmosphere; UV-irradiation;

DOI:10.1002/anie.201910169

Reference yield: 56.0%

C31H45SiTi → (phenylethyl)silane (772-64-5) + 1-(trimethylsilyl)-2-phenylethene (19372-00-0) + (Z)-1-phenyl-2-(trimethylsilyl)ethylene (19319-11-0)

Guidance literature:

With hydrogen; In ⁽²⁾H₈-toluene; at 80 ℃; for 48h; Sealed tube;

DOI:10.1021/om500296h

upstream raw materials:

1-Phenyl-2-(trimethylsilyl)acetylene

styrene

trimethylsilyl iodide

iodobenzene

Downstream raw materials:

stilbene

1,1-diphenyl-2-trimethylsilylethene

(Z)-(1,2-diphenylvinyl)-trimethylsilane

((E)-1,2-diphenylvinyl)trimethylsilane

Refernces

• 1、 Barluenga, Jose,Fernandez-Simon, Jose L.,Concellon, Jose M.,Yus, Miguel. "Highly Stereoselective Synthesis of Vinylsilanes from Carbonyl Compounds". . p. 234 - 236. Retrieved 1988.
• 2、 Soderquist, John A.,Santiago, Braulio. "Alkynylsilanes to cis-vinylsilanes via hydroboration". . p. 5113 - 5117. Retrieved 1990.
• 3、 Huang, Zhidao,Wang, Yulei,Leng, Xuebing,Huang, Zheng. "An Amine-Assisted Ionic Monohydride Mechanism Enables Selective Alkyne cis-Semihydrogenation with Ethanol: From Elementary Steps to Catalysis". supporting information. p. 4824 - 4836. Retrieved 2021/04/07.
• 4、 Moisset, A.,Petit, C.,Petit, M.,Salzemann, C.,Sodreau, A.,Vivien, A.. "Simpler and Cleaner Synthesis of Variously Capped Cobalt Nanocrystals Applied in the Semihydrogenation of Alkynes". supporting information. p. 13972 - 13978. Retrieved 2020/10/09.