1,3,5,7-Cyclooctatetraenyl trimethylsilane

Base Information

• Chemical Name: 1,3,5,7-Cyclooctatetraenyl trimethylsilane
• CAS No.: 55632-03-6
• Molecular Formula: C₁₁H₁₆Si
• Molecular Weight: 176.334
• Nikkaji Number: J2.004.193E
• Mol file: 55632-03-6.mol

Synonyms:1,3,5,7-Cyclooctatetraenyl trimethylsilane;55632-03-6;cyclooctatetraenyl(trimethyl)silane;trimethylsilylcyclooctatetraene;(1,3,5,7-Cyclooctatetraenyl)trimethylsilane

Chemical Property of 1,3,5,7-Cyclooctatetraenyl trimethylsilane

Chemical Property:

• Vapor Pressure: 0.15mmHg at 25°C
• Boiling Point: 222.6°C at 760 mmHg
• Flash Point: 73.8°C
• PSA: 0.00000
• Density: 0.87g/cm³
• LogP: 3.47240
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 176.102127045
• Heavy Atom Count: 12
• Complexity: 239

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C1=CC=CC=CC=C1
• Isomeric SMILES: C[Si](C)(C)/C/1=C/C=C\C=C/C=C1

Technology Process of 1,3,5,7-Cyclooctatetraenyl trimethylsilane

There total 3 articles about 1,3,5,7-Cyclooctatetraenyl 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: 94.0%

chloro-trimethyl-silane (75-77-4) + bromocyclooctatetraene (7567-22-8) → ((1E,3Z,5Z,7Z)-cycloocta-1,3,5,7-tetraen-1-yl)trimethylsilane (55632-03-6)

Guidance literature:

bromocyclooctatetraene; With n-butyllithium; In diethyl ether; hexane; at -78 - -55 ℃; for 2h;

chloro-trimethyl-silane; In diethyl ether; hexane; at 0 ℃; for 2h; Further stages.;

DOI:10.1002/chem.200305114

Reference yield:

1,3,5,7-cyclooctatetraene (629-20-9) → ((1E,3Z,5Z,7Z)-cycloocta-1,3,5,7-tetraen-1-yl)trimethylsilane (55632-03-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: bromine / dichloromethane / 2 h / -78 °C / Schlenk technique; Inert atmosphere

1.2: 3 h / -78 °C / Schlenk technique; Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; cyclohexane / 0.33 h / -78 °C / Schlenk technique; Inert atmosphere

2.2: 2 h / -78 °C / Schlenk technique; Inert atmosphere

With n-butyllithium; bromine; In tetrahydrofuran; dichloromethane; cyclohexane;

DOI:10.1021/acs.orglett.9b03737

Reference yield:

→ ((1E,3Z,5Z,7Z)-cycloocta-1,3,5,7-tetraen-1-yl)trimethylsilane (55632-03-6)

Guidance literature:

upstream raw materials:

chloro-trimethyl-silane

bromocyclooctatetraene

1,3,5,7-cyclooctatetraene

Refernces

• 1、 De Meijere, Armin,Lee, Chih-Hung,Bengtson, Bengt,Pohl, Ehmke,Kozhushkov, Sergei I.,Schreiner, Peter R.,Boese, Roland,Haumann, Thomas. "Preparation and Properties of Centrally Bridgehead-Substituted Hexacyclo[4.4.0.02,1.03,5.04,8.0 7,9]]decanes ( Diademanes ) and Related (CH)10 Hydrocarbons". . p. 5481 - 5488. Retrieved 2003.