4,4,5,5-tetramethyl-2-[5-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophen-2-yl]-[1,3,2]dioxaborolane

Base Information

Chemical Name:4,4,5,5-tetramethyl-2-[5-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophen-2-yl]-[1,3,2]dioxaborolane
CAS No.:635679-14-0
Molecular Formula:C₂₇H₃₇BO₂SSi₂
Molecular Weight:492.638
Hs Code.:

Synonyms:4,4,5,5-tetramethyl-2-[5-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophen-2-yl]-[1,3,2]dioxaborolane

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Chemical Property of 4,4,5,5-tetramethyl-2-[5-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophen-2-yl]-[1,3,2]dioxaborolane

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Technology Process of 4,4,5,5-tetramethyl-2-[5-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophen-2-yl]-[1,3,2]dioxaborolane

There total 3 articles about 4,4,5,5-tetramethyl-2-[5-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophen-2-yl]-[1,3,2]dioxaborolane 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: 59.0%

: 61676-62-8
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 635679-13-9
2-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophene

: 635679-14-0
4,4,5,5-tetramethyl-2-[5-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophen-2-yl]-[1,3,2]dioxaborolane

Guidance literature:: 2-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophene; With tert.-butyl lithium; In tetrahydrofuran; at -70 ℃; for 1.5h;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1002/anie.200352075

Reference yield:

: 123568-21-8
2,5-Dibromo-4-iodotoluene

: 635679-14-0
4,4,5,5-tetramethyl-2-[5-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophen-2-yl]-[1,3,2]dioxaborolane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 76 percent / [PdCl₂(PPh₃)2] / dimethylformamide / 12 h / 80 °C

2.1: 76 percent / CuI; diisopropylamine / [Pd(PPh₃)4] / toluene / 20 h / 80 °C

3.1: tBuLi / tetrahydrofuran / 1.5 h / -70 °C

3.2: 59 percent / tetrahydrofuran / 4 h / 20 °C

With copper(l) iodide; tert.-butyl lithium; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 1.1: Stille cross-coupling / 2.1: Sonogashira cross-coupling;
DOI:10.1002/anie.200352075

Reference yield:

: 635679-12-8
2-(2,5-dibromo-4-methyl-phenyl)-thiophene

: 635679-14-0
4,4,5,5-tetramethyl-2-[5-(4-methyl-2,5-bis-trimethylsilanylethynyl-phenyl)-thiophen-2-yl]-[1,3,2]dioxaborolane

Guidance literature:: Multi-step reaction with 2 steps

1.1: 76 percent / CuI; diisopropylamine / [Pd(PPh₃)4] / toluene / 20 h / 80 °C

2.1: tBuLi / tetrahydrofuran / 1.5 h / -70 °C

2.2: 59 percent / tetrahydrofuran / 4 h / 20 °C

With copper(l) iodide; tert.-butyl lithium; diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; toluene; 1.1: Sonogashira cross-coupling;
DOI:10.1002/anie.200352075