2,5-bis(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)thieno[3,2-b]thiophene

Base Information

• Chemical Name: 2,5-bis(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)thieno[3,2-b]thiophene
• CAS No.: 924894-85-9
• Molecular Formula: C18H26B2O4S2
• Molecular Weight: 392.14900
• Hs Code.: 2934999090
• Mol file: 924894-85-9.mol

Synonyms:4,4,5,5-tetramethyl-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thieno[3,2-b]thiophen-2-yl]-1,3,2-dioxaborolane;

Chemical Property of 2,5-bis(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)thieno[3,2-b]thiophene

Chemical Property:

• Melting Point: 290-294°C
• Boiling Point: 501.0±45.0 °C(Predicted)
• PSA: 93.40000
• Density: 1.18±0.1 g/cm3(Predicted)
• LogP: 3.56120
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

Thieno[3,2-b]thiophene-2,5-diboronic acid bis(pinacol ester) 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Used as a charge transport material in field effect transitors.

Technology Process of 2,5-bis(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)thieno[3,2-b]thiophene

There total 5 articles about 2,5-bis(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)thieno[3,2-b]thiophene 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%

thieno[3,2-b]thiophene (251-41-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4,4,5,5-tetramethyl-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thieno[3,2-b]thiophen-2-yl]-1,3,2-dioxaborolane (924894-85-9)

Guidance literature:

With iridium-bipyridine periodic mesoporous organosilica; In cyclohexane; at 80 ℃; for 12h; regioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1039/c5dt00239g

Reference yield: 61.25%

thieno[3,2-b]thiophene (251-41-2) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 4,4,5,5-tetramethyl-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thieno[3,2-b]thiophen-2-yl]-1,3,2-dioxaborolane (924894-85-9)

Guidance literature:

thieno[3,2-b]thiophene; With n-butyllithium; In tetrahydrofuran; hexanes; at -78 ℃; for 1.16667h; Inert atmosphere; Cooling with ice;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexanes;

With ammonium chloride; In tetrahydrofuran; hexanes; water;

Reference yield: 5.0%

2,5-dibromothieno[3,2-b]thiophene (25121-87-3) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 4,4,5,5-tetramethyl-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thieno[3,2-b]thiophen-2-yl]-1,3,2-dioxaborolane (924894-85-9)

Guidance literature:

2,5-dibromothieno[3,2-b]thiophene; With n-butyllithium; In tetrahydrofuran; hexane; at -70 ℃; for 1h; Inert atmosphere;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; at -70 ℃; Inert atmosphere;

DOI:10.1039/c1jm10961h

upstream raw materials:

thieno[3,2-b]thiophene

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2,5-dibromothieno[3,2-b]thiophene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane