Production Method 1

76-09-5

69249-61-2

850881-09-3

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  2 h, -78 °C
1.2 Reagents: Trimethyl borate ;  12 h, -78 °C
1.3 4 h

Reference

Synthesis and characterization of double-cable oligthiophene/C60 copolymer

Qi, Yuan-jiang; Li, Hui, Boligang/Fuhe Cailiao, 2013, (5), 32-36

Production Method 2

61676-62-8

1693-86-3

850881-09-3

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran
1.2 -

Reference

High-color-quality white electroluminescence and amplified spontaneous emission from a star-shaped single-polymer system with simultaneous three-color emission

Jiu, Yuanda; Wang, Jianyun; Yi, Jianpeng; Liu, Cheng-Fang; Zhang, Xin-Wen; et al, Polymer Chemistry, 2017, 8(5), 851-859

Production Method 3

69249-61-2

61676-62-8

850881-09-3

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 30 min, -78 °C
1.2 -78 °C; -78 °C → rt; overnight, rt
1.3 Solvents: Water ;  rt

Reference

Direct Observation of an Efficient Triplet Exciton Diffusion Process in a Platinum-Containing Conjugated Polymer

Du, Lili; Xiong, Wenjuan; Cheng, Shun-Cheung; Shi, Haiting; Chan, Wai Kin ; et al, Journal of Physical Chemistry Letters, 2017, 8(11), 2475-2479

Production Method 4

69249-61-2

61676-62-8

850881-09-3

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 30 min, -78 °C
1.2 -78 °C; -78 °C → rt; overnight, rt
1.3 Reagents: Water ;  rt

Reference

Impact of Molecular Symmetry on Single-Molecule Conductance

Dell, Emma J.; Capozzi, Brian; DuBay, Kateri H.; Berkelbach, Timothy C.; Moreno, Jose Ricardo; et al, Journal of the American Chemical Society, 2013, 135(32), 11724-11727

Production Method 5

76-09-5

69249-61-2

850881-09-3

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  1 h, -80 °C
1.2 Reagents: Triisopropyl borate ;  -80 °C → rt; 2 h, rt
1.3 overnight, rt

Reference

Dye-functionalized head-to-tail coupled oligo(3-hexylthiophenes)-perylene-oligothiophene dyads for photovoltaic applications

Cremer, Jens; Mena-Osteritz, Elena; Pschierer, Neil G.; Muellen, Klaus; Baeuerle, Peter, Organic & Biomolecular Chemistry, 2005, 3(6), 985-995

Production Method 6

76-09-5

69249-61-2

850881-09-3

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  1 h, -80 °C
1.2 Reagents: Triisopropyl borate ;  -80 °C → rt; 2 h, rt
1.3 overnight, rt

Reference

Kumada Catalyst-Transfer Polycondensation of Thiophene-Based Oligomers: Robustness of a Chain-Growth Mechanism

Beryozkina, Tetyana; Senkovskyy, Volodymyr; Kaul, Elisabeth; Kiriy, Anton, Macromolecules (Washington, 2008, 41(21), 7817-7823

Production Method 7

69249-61-2

61676-62-8

850881-09-3

Reaction Conditions

1.1 Reagents: Magnesium Solvents: Diethyl ether ;  heated; 2 h, rt
1.2 -78 °C; 18 h, rt

Reference

Low-Temperature, Solution-Processed, High-Mobility Polymer Semiconductors for Thin-Film Transistors

Pan, Hualong; Li, Yuning; Wu, Yiliang; Liu, Ping; Ong, Beng S.; et al, Journal of the American Chemical Society, 2007, 129(14), 4112-4113

2-(3-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Raw materials

• 2,3-Dimethylbutane-2,3-diol
• 2-Bromo-3-hexylthiophene
• 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 3-Hexylthiophene

2-(3-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Preparation Products

• 2-(3-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (850881-09-3)

• 1. Examination of the hydrogen-bonding networks in small water clusters (n = 2–5, 13, 17) using absolutely localized molecular orbital energy decomposition analysis?
  Erika A. Cobar,Paul R. Horn,Robert G. Bergman,Martin Head-Gordon Phys. Chem. Chem. Phys., 2012,14, 15328-15339
• 2. Fe3O4/FeS2 heterostructures enable efficient oxygen evolution reaction?
  Xingqun Zheng,Lele Song,Xin Feng,Li Li,Zidong Wei J. Mater. Chem. A, 2020,8, 14145-14151
• 3. Estimating and correcting interference fringes in infrared spectra in infrared hyperspectral imaging
  Ghazal Azarfar,Ebrahim Aboualizadeh,Nicholas M. Walter,Simona Ratti,Camilla Olivieri,Alessandra Norici,Michael Nasse,Achim Kohler,Mario Giordano Analyst, 2018,143, 4674-4683
• 4. Evolved polymerases facilitate selection of fully 2′-OMe-modified aptamers?
  Zhixia Liu,Tingjian Chen,Floyd E. Romesberg Chem. Sci., 2017,8, 8179-8182
• 5. Exceptionally high temperature spin crossover in amide-functionalised 2,6-bis(pyrazol-1-yl)pyridine iron(ii) complex revealed by variable temperature Raman spectroscopy and single crystal X-ray diffraction?
  Max Attwood,Hiroki Akutsu,Lee Martin,Toby J. Blundell,Pierre Le Maguere,Scott S. Turner Dalton Trans., 2021,50, 11843-11851

• Other Chemical Reagents

2-(3-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 850881-09-3): A Comprehensive Overview

2-(3-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 850881-09-3) is a versatile compound that has garnered significant attention in the field of organic synthesis and medicinal chemistry. This compound belongs to the class of boronic esters and is characterized by its unique structural features, which include a hexyl-substituted thiophene moiety and a tetramethyl-substituted dioxaborolane ring. These structural elements contribute to its remarkable reactivity and stability, making it an essential building block in various chemical reactions.

The chemical structure of 2-(3-hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is particularly noteworthy. The thiophene ring provides a conjugated system that enhances the compound's electronic properties, while the hexyl substituent imparts hydrophobicity and influences the compound's solubility and biological activity. The dioxaborolane ring, on the other hand, is a protected form of the boronic acid functionality, which is crucial for its use in Suzuki-Miyaura coupling reactions. This coupling reaction is a widely used method for forming carbon-carbon bonds and is essential in the synthesis of complex organic molecules.

Recent research has highlighted the potential applications of 2-(3-hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in various fields. In medicinal chemistry, this compound has been explored as a precursor for the synthesis of bioactive molecules with potential therapeutic applications. For instance, studies have shown that compounds derived from this boronic ester exhibit anti-inflammatory and anti-cancer properties. The thiophene moiety is known to be a common scaffold in many pharmaceuticals due to its ability to modulate biological targets such as enzymes and receptors.

In materials science, 2-(3-hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane has been used as a building block for the synthesis of conjugated polymers and small molecules with applications in organic electronics. The presence of the thiophene ring and the hexyl substituent makes it an attractive candidate for designing materials with tunable electronic properties. These materials have found use in organic photovoltaics (OPVs), organic light-emitting diodes (OLEDs), and field-effect transistors (FETs).

The synthesis of 2-(3-hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane typically involves several steps. One common approach is to start with 3-hexylthiophene and convert it into the corresponding boronic acid or ester using standard organometallic chemistry techniques. The key step involves the formation of the dioxaborolane ring through a pinacol coupling reaction. This method provides high yields and excellent purity of the final product.

The stability of 2-(3-hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is another important aspect to consider. This compound is generally stable under standard laboratory conditions but should be stored away from moisture and air to prevent degradation. It is also important to note that while the dioxaborolane ring provides protection for the boronic acid functionality during storage and handling, it can be readily converted back to the active boronic acid form under mild conditions using aqueous acidic solutions.

In analytical chemistry, various techniques have been developed to characterize 2-(3-hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane accurately. High-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy are commonly used methods for purity analysis and structural elucidation. These techniques provide detailed information about the compound's chemical structure and help ensure its quality for use in subsequent reactions.

The environmental impact of 2-(3-hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is also an important consideration. While this compound is not classified as hazardous or toxic under current regulations, it is essential to handle it with care to minimize any potential environmental impact. Proper waste disposal methods should be followed to ensure that any residual material does not contaminate water sources or soil.

In conclusion, 2-(3-hexylthiophen-2-yl)-4,4，5，5-tetramethyl-1，3，2-dioxaborolane (CAS No. 850881-09-3) is a valuable compound with a wide range of applications in organic synthesis，medicinal chemistry，and materials science. Its unique chemical structure，combined with its reactivity and stability，makes it an indispensable tool for researchers working in these fields. As research continues to advance，it is likely that new applications for this compound will be discovered，further expanding its utility and importance in modern chemistry.

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