175361-81-6

Basic information

• Product Name: 2,5-Bis-Thiopheneboronic acid pinacol ester
• Synonyms: 2,5-Bis-Thiopheneboronic acid pinacol ester;Thiophene-2,5-diboronic acid bis(pinacol) ester;Thiophene-2,5-diboronic acids pinacol ester;2,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene;2,5-Thiophenediboronic acid bis(pinacol) ester;Bis(4,4,5,5-tetramethyl-1,3-dioxaborolane)-2,5-thiophene;Thiophene-2,5-diboronic acid bis(pinacol) ester 99% (GC);2,2'-(2,5-Thiophenediyl)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane]
• CAS NO: 175361-81-6
• Molecular Formula: C₁₆H₂₆B₂O₄S
• Molecular Weight: 336.06
• Product Categories: Organoborons;Thiophene;Thiophene (TH)
• Mol File: 175361-81-6.mol
• Article Data: 19

Chemical Properties

• Melting Point: 216-220℃
• Boiling Point: 434.3±30.0 °C(Predicted)
• Appearance: /
• Density: 1.08±0.1 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 2,5-Bis-Thiopheneboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Bis-Thiopheneboronic acid pinacol ester(175361-81-6)
• EPA Substance Registry System: 2,5-Bis-Thiopheneboronic acid pinacol ester(175361-81-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 175361-81-6(Hazardous Substances Data)

Usage

Uses

Diboronic acid ester thiophene monomer for polymerization by Suzuki coupling; used for OPV and OFET applications.

Upstream product

• 188290-36-0 thiophene 
• 73183-34-3 bis(pinacol)diborane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 3141-27-3 2,5-dibromothiophen 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 688-74-4 boric acid tributyl ester 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 193978-23-3 2-thiopheneboronic acid pinacol ester 
• 22092-92-8 diisopropopylaminoborane 
• 26076-46-0 thiophene-2,5-diboronic acid 

Downstream Products

• 1310325-02-0 5-bis(N,N’-diphenylanilinyl)-5’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2’-bithiophene 
• 1383534-96-0 N,N-diphenyl-4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl) aniline 

Relevant articles and documents

Iridium-Catalyzed Direct Borylation of Five-Membered Heteroarenes by Bis(pinacolato)diboron: Regioselective, Stoichiometric, and Room Temperature Reactions

An iridium(I) complex generated from 1/ 2[Ir(OMe)(COD)]2 and 4,4′-di-tert-butyl-2,2′-bipyridine catalyzed the direct borylation of 2-substituted thiophenes, furans and pyrroles in stoichiometric amounts relative to bis(pinacolato)diboron in hex

Manganese-Catalyzed C(sp2)-H Borylation of Furan and Thiophene Derivatives

Aryl boronic esters are bench-stable, platform building-blocks that can be accessed through metal-catalyzed aryl C(sp2)-H borylation reactions. C(sp2)-H bond functionalization reactions using rare- and precious-metal catalysts are well established, and while examples utilizing Earth-abundant alternatives have emerged, manganese catalysis remains lacking. The manganese-catalyzed C-H borylation of furan and thiophene derivatives is reported alongside an in situ activation method providing facile access to the active manganese hydride species. Mechanistic investigations showed that blue light irradiation directly affected catalysis by action at the metal center, that C(sp2)-H bond borylation occurs through a C-H metallation pathway, and that the reversible coordination of pinacolborane to the catalyst gave a manganese borohydride complex, which was as an off-cycle resting state.

Iridium/N-heterocyclic carbene-catalyzed C-H borylation of arenes by diisopropylaminoborane

Catalytic C-H borylation of arenes has been widely used in organic synthesis because it allows the introduction of a versatile boron functionality directly onto simple, unfunctionalized arenes. We report herein the use of diisopropylaminoborane as a boron source in C-H borylation of arenes. An iridium(I) complex with 1,3-dicyclohexylimidazol-2-ylidene is found to efficiently catalyze the borylation of arenes and heteroarenes. The resulting aminoborylated products can be converted to the corresponding boronic acid derivatives simply by treatment with suitable diols or diamines.