883742-29-8

Basic information

• Product Name: 2-(4-Hexyl-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-(4-Hexyl-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-Hexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene;2-(4-Hexyl-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 4-Hexyl-2-thiopheneboronic Acid Pinacol Ester;2-(4-Hexylthiophen-2-yl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane;3-Hexyl-5-thiopheneboronicacidpinacolester
• CAS NO: 883742-29-8
• Molecular Formula: C16H27BO2S
• Molecular Weight: 294.26038
• Mol File: 883742-29-8.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 385.589°C at 760 mmHg
• Flash Point: 186.998°C
• Appearance: /
• Density: 1.005g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4950-1.4990
• Storage Temp.: 0-10°C
• CAS DataBase Reference: 2-(4-Hexyl-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Hexyl-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(883742-29-8)
• EPA Substance Registry System: 2-(4-Hexyl-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(883742-29-8)

Safety Data

• Hazardous Substances Data: 883742-29-8(Hazardous Substances Data)

Usage

General Description

2-(4-Hexyl-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a chemical compound often used in the field of synthetic chemistry. Its molecular formula is C16H26BOS2 and it has a molar mass of 298.16 g/mol. This substance belongs to the class of organometallic compounds characterized by their content of carbon-metal bonds. In particular, it contains a boron atom in its structure. 2-(4-Hexyl-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane has an intrinsic reactivity which makes it suitable to be used in Suzuki coupling reactions, a common method for generating carbon-carbon bonds in the laboratory. It is also commonly used in the synthesis of dyes, pharmaceuticals, and organic semiconductors.

InChI:InChI=1/C16H27BO2S/c1-6-7-8-9-10-13-11-14(20-12-13)17-18-15(2,3)16(4,5)19-17/h11-12H,6-10H2,1-5H3

Upstream product

• 1693-86-3 3-hexylthiophene 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 210705-84-3 2-bromo-4-n-hexylthiophene 
• 3761-92-0 n-hexylmagnesium bromide 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 761416-46-0 4,7-bis-(4-hexyl-thiophen-2-yl)-benzo[1,2,5]thiadiazole 
• 135926-93-1 3,4'-dihexyl-2,2'-bithiophene 
• 1432475-92-7 4-[3,4’-dihexyl(2,2’-bithiophene)-5-yl]-N,N-diphenylbenzenamine 

Relevant articles and documents

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.

Dibenzothiophene pyrrole functional dye containing phenoxy long carbon chain and application thereof (by machine translation)

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Solution processed bulk heterojunction solar cells based on A-D-A small molecules with a dihydroindoloindole (DINI) central donor and different acceptor end groups

Four acceptor-donor-acceptor (A-D-A) small molecules with dihydroindoloindole (DINI) as the central donor unit and different acceptor end groups such as dicyanovinylene (DCV), indenedione (IND), cyanoacrylate (CA) and rhodanine (Rho) linked through bithiophene as the π-linker, DINI-DCV, DINI-IND, DINI-CA and DINI-Rho, were designed and synthesized for the application as donor materials along with PC71BM as an acceptor for solution processed organic bulk heterojunction solar cells. The effect of acceptor end groups on the photovoltaic performance was investigated. The organic solar cells (OSCs) based on as cast DINI-IND showed the highest power conversion efficiency of 3.04%, as cast DINI-CA showed the lowest PCE of 1.63% and the other two exhibit a PCE in between them. These results showed that acceptor end groups affect the overall performance of the cells. The PCE of OSCs has been further improved up to 7.04% and 6.16% employing two-step annealing (TSA) treated DIN-IND:PC71BM (1:2) and DIN-CN:PC71BM (1:2), respectively. The enhancement in the PCE of OSCs with TSA treated active layers is attributed to the better nanophase morphology, the increase in the crystalline nature and light harvesting efficiency and more balanced charge transport and charge collection probability.