Production Method 1

2404-87-7

25015-63-8

960116-25-0

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Catalysts: Manganese, (dihydrogen-H,H′)bis[1,2-ethanediylbis[dimethylphosphine]-P,P′]hydro- Solvents: Hexane ;  24 h, 60 °C

Reference

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

Britton, Luke; Skrodzki, Maciej; Nichol, Gary S.; Dominey, Andrew P.; Pawluc, Piotr; et al, ACS Catalysis, 2021, 11(12), 6857-6864

Production Method 2

2404-87-7

73183-34-3

960116-25-0

Reaction Conditions

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium ,  4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine Solvents: Tetrahydrofuran ;  15 - 30 min, rt
1.2 24 h, 65 °C

Reference

Iridium-catalyzed silylation of five-membered heteroarenes: high sterically derived selectivity from a pyridyl-imidazoline ligand

Karmel, Caleb; Rubel, Camille Z.; Kharitonova, Elena V.; Hartwig, John F., ChemRxiv, 2019, 1, 1-10

Production Method 3

2404-87-7

73183-34-3

960116-25-0

Reaction Conditions

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium ,  5-Methyl-2-(3-thienyl)pyridine Solvents: Tetrahydrofuran ;  2 min, rt
1.2 24 h, 60 °C

Reference

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Hoque, Emdadul Md; Hassan, Mirja Mahamudul Md; Chattopadhyay, Buddhadeb, Journal of the American Chemical Society, 2021, 143(13), 5022-5037

Production Method 4

2404-87-7

25015-63-8

960116-25-0

Reaction Conditions

1.1 Reagents: 3,3-Dimethyl-1-butene Catalysts: (1,3-Dihydro-1,3,4,5-tetramethyl-2H-imidazol-2-ylidene)methyl[(1,2,3,4,5-η)-1,2,… Solvents: Benzene ;  1 h, 70 °C
1.2 Solvents: Benzene ;  1 h, 70 °C

Reference

C-H Bond activation/borylation of furans and thiophenes catalyzed by a half-sandwich iron N-heterocyclic carbene complex

Hatanaka, Tsubasa; Ohki, Yasuhiro; Tatsumi, Kazuyuki, Chemistry - An Asian Journal, 2010, 5(7), 1657-1666

Production Method 5

2404-87-7

73183-34-3

960116-25-0

Reaction Conditions

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium ,  4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine Solvents: Tetrahydrofuran ;  15 - 30 min, rt
1.2 rt; 24 h, 65 °C

Reference

Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand

Karmel, Caleb; Rubel, Camille Z.; Kharitonova, Elena V.; Hartwig, John F., Angewandte Chemie, 2020, 59(15), 6074-6081

Production Method 6

2404-87-7

76347-13-2

960116-25-0

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  rt → 0 °C; 0 °C; 2 h, rt; rt → -78 °C
1.2 -78 °C; -78 °C → rt; overnight, rt

Reference

Imidazopyrazines as protein kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of kinase-mediated diseases

, World Intellectual Property Organization, , ,

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)-4-phenylthiophene Raw materials

• 3-Phenylthiophene
• 4,4,5,5-tetramethyl-2-(propan-2-yl)-1,3,2-dioxaborolane
• Bis(pinacolato)diborane
• Pinacolborane

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)-4-phenylthiophene Preparation Products

• 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)-4-phenylthiophene (960116-25-0)

• 1. An aptasensor for detection of potassium ions based on RecJf exonuclease mediated signal amplification
  Bidou Wang,Xifeng Chen Analyst, 2014,139, 5695-5699
• 2. An approach to biodegradable star polymeric architectures using disulfide coupling?
  Jingquan Liu,Huiyun Liu,Zhongfan Jia,Volga Bulmus,Thomas P. Davis Chem. Commun., 2008, 6582-6584
• 3. An amide probe as a selective Al3+ and Fe3+ sensor inside the HeLa and a549 cell lines: Pictet–Spengler reaction for the rapid detection of tryptophan amino acid?
  Bidyut Kumar Kundu,Rinky Singh,Ritudhwaj Tiwari,Debasis Nayak New J. Chem., 2019,43, 4867-4877
• 4. An artificial CO-releasing metalloprotein built by histidine-selective metallation?
  Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?o Chem. Commun., 2015,51, 3993-3996
• 5. An antioxidative galactomannan extracted from Chinese Sesbania cannabina enhances immune activation of macrophage cells?
  Chongyang Zhu,Xiaojia Bian,Xin Jia,Ning Tang,Yongqiang Cheng Food Funct., 2020,11, 10635-10644

Comprehensive Guide to 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)-4-phenylthiophene (CAS No. 960116-25-0)

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)-4-phenylthiophene (CAS No. 960116-25-0) is a highly versatile boronic ester derivative widely used in organic synthesis, pharmaceuticals, and material science. This compound belongs to the class of arylboronates, which are crucial intermediates in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic chemistry. The presence of the tetramethyl-1,3,2-dioxaborolane group enhances its stability and reactivity, making it a preferred choice for researchers and industrial applications.

The molecular structure of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)-4-phenylthiophene combines a thiophene ring with a phenyl substituent and a boronate ester functional group. This unique arrangement allows for diverse applications, including the synthesis of π-conjugated polymers, OLED materials, and pharmaceutical intermediates. Its stability under ambient conditions and compatibility with various reaction conditions make it a valuable tool for chemists exploring new synthetic pathways.

In recent years, the demand for boronic acid derivatives like 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)-4-phenylthiophene has surged due to their role in developing targeted drug delivery systems and bioimaging agents. Researchers are particularly interested in its potential for creating fluorescent probes and sensors, leveraging the thiophene moiety's electronic properties. This aligns with the growing trend of precision medicine and theranostics, where multifunctional compounds are essential.

From an industrial perspective, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)-4-phenylthiophene is a key intermediate in the production of organic electronic materials. Its incorporation into polymer solar cells and thin-film transistors has been extensively studied, driven by the global push for renewable energy solutions and flexible electronics. The compound's ability to facilitate C-C bond formation under mild conditions makes it attractive for sustainable chemistry initiatives.

For those searching for "boronate ester applications" or "Suzuki coupling reagents," this compound exemplifies the intersection of synthetic efficiency and functional diversity. Its compatibility with microwave-assisted synthesis and flow chemistry setups further enhances its appeal in high-throughput research environments. Additionally, its role in metal-organic frameworks (MOFs) and covalent organic frameworks (COFs) is an emerging area of interest, particularly for gas storage and catalysis applications.

Safety and handling of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)-4-phenylthiophene follow standard laboratory protocols for boronic esters. While not classified as hazardous, proper storage in a cool, dry place under inert atmosphere is recommended to maintain its stability. Researchers often inquire about "boronate shelf life" and "handling precautions," underscoring the need for clear technical documentation.

The future outlook for 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)-4-phenylthiophene is closely tied to advancements in green chemistry and catalytic processes. As industries seek alternatives to traditional palladium-based catalysts, this compound's role in ligand design and transition-metal-free coupling reactions gains prominence. Its relevance in academic research and industrial R&D ensures sustained interest, with patent filings and publications reflecting its growing importance.

• 885692-91-1(4,4,5,5-Tetramethyl-2-(3-methylthiophen-2-yl)-1,3,2-dioxaborolane)
• 2223042-41-7(4-(2-Trifluoromethylphenyl)thiophene-2-boronic acid pinacol ester)
• 1402234-07-4(4-(4-Trifluoromethylphenyl)thiophene-2-boronic acid pinacol ester)
• 1402227-79-5(4-(4-Chlorophenyl)thiophene-2-boronic acid pinacol ester)
• 635305-48-5(4,4,5,5-Tetramethyl-2-(4-methylthiophen-2-yl)-1,3,2-dioxaborolane)
• 942070-28-2(2,2'-(3-Methylthiophene-2,5-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane))
• 2223011-20-7(4-(3-Trifluoromethylphenyl)thiophene-2-boronic acid pinacol ester)
• 1402166-52-2(4-(2-Thienyl)thiophene-2-boronic acid pinacol ester)
• 1402240-72-5(4-(4-Pyridyl)thiophene-2-boronic acid pinacol ester)
• 1402166-51-1(4-(3-Thienyl)thiophene-2-boronic acid pinacol ester)