o-bis(ethynyl)tolane

Base Information

• Chemical Name: o-bis(ethynyl)tolane
• CAS No.: 27499-64-5
• Molecular Formula: C₁₈H₁₀
• Molecular Weight: 226.277
• Mol file: 27499-64-5.mol

Synonyms:o-bis(ethynyl)tolane

Chemical Property of o-bis(ethynyl)tolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of o-bis(ethynyl)tolane

There total 15 articles about o-bis(ethynyl)tolane 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: 99.0%

2,2'-bis(trimethylsilylethynyl)diphenylacetylene (120651-34-5) → o-bis(ethynyl)tolane (27499-64-5)

Guidance literature:

With methanol; potassium carbonate; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ja8038213

Reference yield: 46.0%

2,2'-dibromotolane (38399-13-2) + trimethylsilylacetylene (1066-54-2) → o-bis(ethynyl)tolane (27499-64-5)

Guidance literature:

2,2'-dibromotolane; trimethylsilylacetylene; With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 80 ℃; for 24h; Inert atmosphere;

With methanol; potassium carbonate; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1039/c9dt02525a

Reference yield:

2,3-dibromobenzene (583-53-9) → o-bis(ethynyl)tolane (27499-64-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / copper(I)iodide, tetrakis(triphenylphosphine)palladium / triethylamine / 7 h / 70 °C

2: 57 percent / copper(I)iodide, tetrakis(triphenyl-phosphine)palladium / triethylamine / 4 h / 80 °C

3: 84 percent / potassium fluoride / H₂O; dimethylformamide / 4 h / Ambient temperature

With potassium fluoride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In water; triethylamine; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)89821-5

upstream raw materials:

2,2'-Bis-<α,β-dibrom-aethyl>-diphenyl-acetylen

2,2'-bis(trimethylsilylethynyl)diphenylacetylene

2,2'-dibromotolane

trimethylsilylacetylene

Downstream raw materials:

chrysene

11-Methyl-11H-benzofluorene

(3,4:7,8-dibenzodeca-3,7-diene-1,5,9-triyne-1,10-diyl)diphenylgermane

Fe(C₅H₄P(C₆H₅)2)2Pt((CCC₆H₄C)2)

Refernces

• 1、 Resa, Sandra,Miguel, Delia,Guisán-Ceinos, Santiago,Mazzeo, Giuseppe,Choquesillo-Lazarte, Duane,Abbate, Sergio,Crovetto, Luis,Cárdenas, Diego J.,Carre?o, M. Carmen,Ribagorda, María,Longhi, Giovanna,Mota, Antonio J.,álvarez de Cienfuegos, Luis,Cuerva, Juan M.. "Sulfoxide-Induced Homochiral Folding of ortho-Phenylene Ethynylenes (o-OPEs) by Silver(I) Templating: Structure and Chiroptical Properties". . p. 2653 - 2662. Retrieved 2018/02/06.
• 2、 Holmes, Daniel,Lee, Sang Yeul,Lotz, Sabine D.,Nguyen, Son C.,Schaller, Gaston R.,Schmidt-Radde, Rachel H.,Vollhardt, K. Peter C.. "(η6-[7]Heliphene)tricarbonylchromium via an Optimized Preparation of [7]Heliphene". . p. 2038 - 2054. Retrieved 2015/07/15.