Production Method 1

2304989-47-5

73183-34-3

879275-72-6

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  12 h, 80 °C; 80 °C → rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt

Reference

The ortho Difluoroalkylation of Aryliodanes with Enol Silyl Ethers: Rearrangement Enabled by a Fluorine Effect

Huang, Xin; et al, Angewandte Chemie, 2019, 58(18), 5956-5961

Production Method 2

86340-78-5

879275-72-6

Reaction Conditions

1.1 Reagents: Trimethylsilyl triflate Solvents: Dichloromethane ;  5 min, rt; rt → -78 °C
1.2 5 min, -78 °C
2.1 Reagents: Potassium tert-butoxide Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  12 h, 80 °C; 80 °C → rt
2.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt

Reference

The ortho Difluoroalkylation of Aryliodanes with Enol Silyl Ethers: Rearrangement Enabled by a Fluorine Effect

Huang, Xin; et al, Angewandte Chemie, 2019, 58(18), 5956-5961

Production Method 3

2712-78-9

86340-78-5

879275-72-6

Reaction Conditions

1.1 Solvents: Dichloromethane ;  5 min, rt; rt → -78 °C
1.2 12 h, -78 °C
2.1 Reagents: Potassium tert-butoxide Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  12 h, 80 °C; 80 °C → rt
2.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt

Reference

The ortho Difluoroalkylation of Aryliodanes with Enol Silyl Ethers: Rearrangement Enabled by a Fluorine Effect

Huang, Xin; et al, Angewandte Chemie, 2019, 58(18), 5956-5961

Production Method 4

3240-34-4

86340-78-5

879275-72-6

Reaction Conditions

1.1 Reagents: Trimethylsilyl triflate Solvents: Dichloromethane ;  5 min, rt; rt → -78 °C
1.2 5 min, -78 °C
2.1 Reagents: Potassium tert-butoxide Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  12 h, 80 °C; 80 °C → rt
2.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt

Reference

The ortho Difluoroalkylation of Aryliodanes with Enol Silyl Ethers: Rearrangement Enabled by a Fluorine Effect

Huang, Xin; et al, Angewandte Chemie, 2019, 58(18), 5956-5961

Production Method 5

3240-34-4

86340-78-5

879275-72-6

Reaction Conditions

1.1 Reagents: Trimethylsilyl triflate Solvents: Dichloromethane ;  5 min, rt; rt → -78 °C
1.2 5 min, -78 °C
2.1 Reagents: Potassium tert-butoxide Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  12 h, 80 °C; 80 °C → rt
2.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt

Reference

The ortho Difluoroalkylation of Aryliodanes with Enol Silyl Ethers: Rearrangement Enabled by a Fluorine Effect

Huang, Xin; et al, Angewandte Chemie, 2019, 58(18), 5956-5961

Production Method 6

22070-00-4

879275-72-6

Reaction Conditions

1.1 Reagents: Sodium perborate (NaBO3) tetrahydrate Solvents: Acetic acid ;  30 min, rt; rt → 50 °C; overnight, 50 °C
2.1 Reagents: Trimethylsilyl triflate Solvents: Dichloromethane ;  5 min, rt; rt → -78 °C
2.2 5 min, -78 °C
3.1 Reagents: Potassium tert-butoxide Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  12 h, 80 °C; 80 °C → rt
3.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt

Reference

The ortho Difluoroalkylation of Aryliodanes with Enol Silyl Ethers: Rearrangement Enabled by a Fluorine Effect

Huang, Xin; et al, Angewandte Chemie, 2019, 58(18), 5956-5961

2-2-(Difluoromethyl)phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Raw materials

• Bis(trifluoroacetoxy)iodobenzene
• Iodobenzene diacetate
• 2,2-Difluoro-2-(2-iodophenyl)-1-phenylethanone
• Benzene-d, 2-iodo-
• Bis(pinacolato)diborane
• Silane, [(2,2-difluoro-1-phenylethenyl)oxy]trimethyl-

2-2-(Difluoromethyl)phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Preparation Products

• 2-2-(Difluoromethyl)phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (879275-72-6)

• 1. An assessment of strategies for the development of solid-state adsorbents for vehicular hydrogen storage
  Mark D. Allendorf,Alauddin Ahmed,Tom Autrey,Jeffrey Camp,Eun Seon Cho,Maciej Haranczyk,Abhi Karkamkar,Di-Jia Liu,Katie R. Meihaus,Iffat H. Nayyar,Roman Nazarov,Donald J. Siegel,Vitalie Stavila,Jeffrey J. Urban,Srimukh Prasad Veccham,Brandon C. Wood Energy Environ. Sci., 2018,11, 2784-2812
• 2. An intensified π-hole in beryllium-doped boron nitride meshes: its determinant role in CO2 conversion into hydrocarbon fuels?
  Luis Miguel Azofra,Douglas R. MacFarlane,Chenghua Sun Chem. Commun., 2016,52, 3548-3551
• 3. An integrated process of CO2 capture and in situ hydrogenation to formate using a tunable ethoxyl-functionalized amidine and Rh/bisphosphine system?
  Yu-Nong Li,Liang-Nian He,Xian-Dong Lang,Xiao-Fang Liu,Shuai Zhang RSC Adv., 2014,4, 49995-50002
• 4. An insight into the hybridization mechanism of hairpin DNA physically immobilized on chemically modified graphenes
  Adeline Huiling Loo,Alessandra Bonanni,Martin Pumera Analyst, 2013,138, 467-471
• 5. An alkynylboronatecycloaddition strategy to functionalised benzyne derivatives?
  James D. Kirkham,Patrick M. Delaney,George J. Ellames,Eleanor C. Row,Joseph P. A. Harrity Chem. Commun., 2010,46, 5154-5156

Recent Advances in the Application of 2-2-(Difluoromethyl)phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 879275-72-6) in Chemical Biology and Pharmaceutical Research

The compound 2-2-(Difluoromethyl)phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 879275-72-6) has recently garnered significant attention in the field of chemical biology and pharmaceutical research. This boronic ester derivative is widely recognized for its utility as a key intermediate in Suzuki-Miyaura cross-coupling reactions, which are pivotal in the synthesis of complex organic molecules, including pharmaceuticals and bioactive compounds. Recent studies have highlighted its role in the development of novel therapeutic agents, particularly in oncology and infectious disease research.

One of the most notable applications of this compound is in the synthesis of boron-containing drugs, which leverage the unique properties of boron to enhance drug efficacy and selectivity. For instance, researchers have utilized 2-2-(Difluoromethyl)phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane to develop proteasome inhibitors with improved pharmacokinetic profiles. These inhibitors have shown promising results in preclinical models of multiple myeloma and other hematologic malignancies, underscoring the compound's potential in targeted cancer therapy.

In addition to its applications in drug development, recent studies have explored the use of this boronic ester in bioorthogonal chemistry. Its stability under physiological conditions and reactivity with various functional groups make it an ideal candidate for labeling and imaging applications. For example, researchers have successfully employed it in the development of fluorescent probes for real-time monitoring of enzymatic activity in live cells, providing new insights into cellular processes and disease mechanisms.

Another area of interest is the compound's role in the synthesis of boron neutron capture therapy (BNCT) agents. BNCT is an emerging radiotherapy approach that utilizes boron-10 isotopes to selectively target and destroy cancer cells. The incorporation of 2-2-(Difluoromethyl)phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane into BNCT agents has been shown to enhance their tumor-targeting capabilities and reduce off-target effects, paving the way for more effective and safer cancer treatments.

Despite these advancements, challenges remain in the large-scale synthesis and purification of this compound, as well as in optimizing its reactivity for specific applications. Recent efforts have focused on developing more efficient synthetic routes and improving the stability of the boronic ester under various conditions. These innovations are expected to further expand its utility in chemical biology and pharmaceutical research.

In conclusion, 2-2-(Difluoromethyl)phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 879275-72-6) represents a versatile and valuable tool in modern drug discovery and chemical biology. Its applications span from the synthesis of novel therapeutics to advanced imaging techniques, highlighting its broad potential. Ongoing research and development efforts are likely to uncover even more innovative uses for this compound, solidifying its importance in the field.

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