TMSEP

Base Information

• Chemical Name: TMSEP
• CAS No.: 317809-68-0
• Molecular Formula: C₃₂H₃₀Si₂
• Molecular Weight: 470.761
• Mol file: 317809-68-0.mol

Synonyms:6,13-bis(2-(trimethylsilyl)ethynyl)pentacene

Chemical Property of TMSEP

Chemical Property:

Purity/Quality:

98%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of TMSEP

There total 4 articles about TMSEP 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: 82.0%

6,13-pentacenequinone (3029-32-1) + trimethylsilylacetylene (1066-54-2) → 6,13-bis(2-(trimethylsilyl)ethynyl)pentacene (317809-68-0)

Guidance literature:

trimethylsilylacetylene; With isopropylmagnesium chloride; In tetrahydrofuran; at 60 ℃; for 0.25h;

6,13-pentacenequinone; In tetrahydrofuran; at 60 ℃;

With hydrogenchloride; tin(ll) chloride; In tetrahydrofuran; water; Further stages.;

DOI:10.1021/ol0167356

Reference yield: 82.0%

6,13-pentacenequinone (3029-32-1) + (trimethylsilyl)ethynylmagnesium bromide (61210-52-4) → 6,13-bis(2-(trimethylsilyl)ethynyl)pentacene (317809-68-0)

Guidance literature:

6,13-pentacenequinone; (trimethylsilyl)ethynylmagnesium bromide; In tetrahydrofuran; at 60 ℃;

With tin(ll) chloride; In tetrahydrofuran; at 60 ℃; Further stages.;

DOI:10.1021/ol0167356

Reference yield:

o-phthalic dicarboxaldehyde (643-79-8) → 6,13-bis(2-(trimethylsilyl)ethynyl)pentacene (317809-68-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: KOH / ethanol

2.1: i-PrMgCl / tetrahydrofuran

2.2: SnCl₂; aq. HCl

With potassium hydroxide; isopropylmagnesium chloride; In tetrahydrofuran; ethanol;

DOI:10.1021/ja040243h

upstream raw materials:

6,13-pentacenequinone

(trimethylsilyl)ethynylmagnesium bromide

trimethylsilylacetylene

o-phthalic dicarboxaldehyde

Refernces

• 1、 Jia, Zhiying,Li, Shi,Nakajima, Kiyohiko,Kanno, Ken-Ichiro,Song, Zhiyi,Takahashi, Tamotsu. "Application of zirconacyclopentadienes (metalla-heterocycles) and cross-coupling for the convenient preparative method of 6,13-disubstituted pentacene". . p. 1495 - 1506. Retrieved 2013/08/23.
• 2、 Anthony, John E.,Eaton, David L.,Parkin, Sean R.. "A road map to stable, soluble, easily crystallized pentacene derivatives". . p. 15 - 18. Retrieved 2007/10/03.