2,3-bis[(trimethylsilyl)ethynyl]naphthalene

Base Information

• Chemical Name: 2,3-bis[(trimethylsilyl)ethynyl]naphthalene
• CAS No.: 256439-91-5
• Molecular Formula: C₂₀H₂₄Si₂
• Molecular Weight: 320.582
• Mol file: 256439-91-5.mol

Synonyms:2,3-bis[(trimethylsilyl)ethynyl]naphthalene

Chemical Property of 2,3-bis[(trimethylsilyl)ethynyl]naphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-bis[(trimethylsilyl)ethynyl]naphthalene

There total 1 articles about 2,3-bis[(trimethylsilyl)ethynyl]naphthalene 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: 81.0%

2,3-dibromonaphthalene (13214-70-5) + ((trimethylsilyl)ethynyl)zinc(II) chloride (78389-87-4) → 2,3-bis[(trimethylsilyl)ethynyl]naphthalene (256439-91-5)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In diethyl ether; Heating;

DOI:10.1021/ol991254w

Reference yield:

2,3-bis[(trimethylsilyl)ethynyl]naphthalene (256439-91-5) → Tetracen (92-24-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 0.36 g / NBS; AgNO₃ / acetone / 10 h / 25 °C

2: 0.27 g / 1,4-cyclohexadiene; N₂ / benzene / 2 h / 180 °C / 15514.9 Torr

3: PdCl₂dppf / diethyl ether / Heating

4: NaH; MeOH / tetrahydrofuran / 2 h

5: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr

With methanol; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-Bromosuccinimide; cyclohexa-1,4-diene; nitrogen; sodium hydride; silver nitrate; In tetrahydrofuran; diethyl ether; acetone; benzene; 1: desilylative bromination / 2: cycloaromatization / 3: Condensation / 4: desilylation / 5: cycloaromatization;

DOI:10.1021/ol991254w

Reference yield:

2,3-bis[(trimethylsilyl)ethynyl]naphthalene (256439-91-5) → C60H78O6Si (871951-35-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.95 g / KOH / diethyl ether; methanol / 0.5 h / 20 °C

2: 87 percent / CpCo(CO)2 / o-xylene / 10 h / Heating; irradiation

3: 81 percent / iodine monochloride / CCl₄; CH₂Cl₂ / 0 - 20 °C

4: diisopropylamine; copper(I) iodide / PdCl₂(PPh₃)2 / 1 h / Heating

5: 0.250 g / KOH / diethyl ether; methanol / 0.5 h / 20 °C

6: 61 percent / CpCo(CO)2 / o-xylene; tetrahydrofuran / 0.25 h / Heating; irradiation

7: 82 percent / DCC; 4-DMAP / CH₂Cl₂ / 0 - 20 °C

With dmap; potassium hydroxide; copper(l) iodide; dicarbonylcyclopentadienylcobalt; Iodine monochloride; diisopropylamine; dicyclohexyl-carbodiimide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; o-xylene; 4: Sonogashira reaction;

DOI:10.1016/j.tetlet.2005.09.174

upstream raw materials:

2,3-dibromonaphthalene

((trimethylsilyl)ethynyl)zinc(II) chloride

Downstream raw materials:

C₆₀H₇₈O₆Si

Tetracen