Production Method 1

1692-25-7

126-30-7

845885-86-1

Reaction Conditions

1.1 Solvents: Toluene ;  4 h, reflux

Reference

Heteroaryl-Heteroaryl Suzuki-Miyaura Anhydrous Cross-Coupling Reactions Enabled by Trimethyl Borate

Kassel, Vincent M.; et al, Journal of the American Chemical Society, 2021, 143(34), 13845-13853

Production Method 2

201733-56-4

2642631-23-8

845885-86-1

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Catalysts: Bis(1,5-cyclooctadiene)nickel ,  1H-Imidazolium, 1,3-dicyclohexyl-, tetrafluoroborate(1-) (1:1) Solvents: 1,4-Dioxane ;  20 h, 110 °C

Reference

Ni-Catalyzed Borylation of Aryl Sulfoxides

Huang, Mingming; et al, Chemistry - A European Journal, 2021, 27(31), 8149-8158

Production Method 3

118-72-9

1120-90-7

845885-86-1

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Cuprous iodide Solvents: N-Methyl-2-pyrrolidone ;  16 h, 100 °C
1.2 Reagents: m-Chloroperbenzoic acid Solvents: Dichloromethane ;  0 °C; 0 °C → rt; 12 h, rt
2.1 Reagents: Sodium tert-butoxide Catalysts: Bis(1,5-cyclooctadiene)nickel ,  1H-Imidazolium, 1,3-dicyclohexyl-, tetrafluoroborate(1-) (1:1) Solvents: 1,4-Dioxane ;  20 h, 110 °C

Reference

Ni-Catalyzed Borylation of Aryl Sulfoxides

Huang, Mingming; et al, Chemistry - A European Journal, 2021, 27(31), 8149-8158

Production Method 4

1692-25-7

126-30-7

845885-86-1

Reaction Conditions

1.1 Solvents: Toluene ;  reflux

Reference

Cu-catalyzed cross-coupling reactions of vinyl epoxide with organoboron compounds: access to homoallylic alcohols

Lu, Xiao-Yu; et al, RSC Advances, 2018, 8(72), 41561-41565

Production Method 5

1692-25-7

126-30-7

845885-86-1

Reaction Conditions

Reference

1,3-Dicyclohexylimidazol-2-ylidene as a Superior Ligand for the Nickel-Catalyzed Cross-Couplings of Aryl and Benzyl Methyl Ethers with Organoboron Reagents

Tobisu, Mamoru; et al, Organic Letters, 2014, 16(21), 5572-5575

Production Method 6

2649116-18-5

845885-86-1

Reaction Conditions

1.1 Reagents: m-Chloroperbenzoic acid Solvents: Dichloromethane ;  0 °C; 0 °C → rt; 12 h, rt
2.1 Reagents: Sodium tert-butoxide Catalysts: Bis(1,5-cyclooctadiene)nickel ,  1H-Imidazolium, 1,3-dicyclohexyl-, tetrafluoroborate(1-) (1:1) Solvents: 1,4-Dioxane ;  20 h, 110 °C

Reference

Ni-Catalyzed Borylation of Aryl Sulfoxides

Huang, Mingming; et al, Chemistry - A European Journal, 2021, 27(31), 8149-8158

3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine Raw materials

• Pyridin-3-ylboronic acid
• Bis(neopentyl glycolato)diboron
• 3-[(2,6-Dimethylphenyl)thio]pyridine
• 3-[(2,6-Dimethylphenyl)sulfinyl]pyridine
• 2,6-Dimethylthiophenol
• 2,2-Dimethyl-1,3-propanediol
• 3-Iodopyridine

3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine Preparation Products

• 3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine (845885-86-1)

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• 4. Emergence of cationic polyamine dendrimersomes: design, stimuli sensitivity and potential biomedical applications
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• 5. Esterase-responsive polymeric prodrug-based tumor targeting nanoparticles for improved anti-tumor performance against colon cancer?
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Pyridines and derivatives
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives

Introduction to 3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine (CAS No. 845885-86-1) and Its Emerging Applications in Chemical Biology

3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine, identified by the chemical identifier CAS No. 845885-86-1, is a specialized boronic acid derivative that has garnered significant attention in the field of chemical biology due to its unique structural and functional properties. This compound belongs to the class of organoboron compounds, which are widely recognized for their role in cross-coupling reactions and as intermediates in pharmaceutical synthesis. The presence of a dimethyl-substituted dioxaborane moiety and a pyridine ring endows this molecule with distinctive reactivity and binding capabilities, making it a valuable tool in both academic research and industrial applications.

The pyridine core of this compound serves as a versatile pharmacophore, capable of interacting with various biological targets through hydrogen bonding and π-stacking interactions. This feature has been leveraged in the development of small-molecule inhibitors and probes for studying protein-protein interactions, enzyme mechanisms, and cellular signaling pathways. Furthermore, the boronic acid functionality at the 2-position allows for participation in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic organic chemistry that enables the construction of complex molecular architectures with high precision.

In recent years, there has been a surge in the use of organoboron compounds like 3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine in drug discovery efforts. The ability to introduce boron atoms into molecular frameworks has been linked to enhanced metabolic stability and improved pharmacokinetic profiles in drug candidates. This trend is particularly evident in the design of kinase inhibitors, where boronic acids are often incorporated to modulate enzyme activity through covalent binding or allosteric regulation. The dimethyl-substituted dioxaborane moiety further enhances the stability of the boronic acid group under physiological conditions, making it an attractive scaffold for medicinal chemists.

One of the most compelling aspects of this compound is its potential application in bioconjugation chemistry. Boronic acids are well-known for their ability to form reversible covalent bonds with diols under acidic conditions, a phenomenon known as "click chemistry." This property has been exploited to develop strategies for site-specific labeling of biomolecules such as proteins and nucleic acids. The pyridine ring can also be functionalized to attach additional biomolecular probes or therapeutic agents, expanding the utility of 3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine as a versatile building block in biopharmaceutical research.

Recent studies have highlighted the role of this compound in developing novel therapeutic agents targeting neurological disorders. The interaction between pyridine-containing molecules and neuroreceptors has been extensively studied due to their potential as pharmacological tools. For instance, derivatives of this compound have been investigated for their ability to modulate neurotransmitter release or inhibit aberrant signaling pathways associated with conditions such as Alzheimer's disease and Parkinson's disease. The boronic acid group provides an additional layer of functionality that can be exploited for targeted delivery or controlled release mechanisms.

The synthesis of 3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine presents an interesting challenge from a synthetic chemistry perspective. The integration of the dimethyl-substituted dioxaborane unit with the pyridine scaffold requires precise control over reaction conditions to ensure high yield and purity. Advances in transition-metal catalysis have made it possible to achieve these transformations under mild conditions while maintaining excellent regioselectivity. These methodologies have not only streamlined the production process but also opened up new avenues for exploring related derivatives with tailored properties.

From an industrial standpoint, the demand for high-quality boronic acid derivatives like this one continues to grow alongside advancements in pharmaceutical manufacturing technologies. Companies specializing in fine chemicals have invested heavily in optimizing synthetic routes to meet market needs efficiently. The reliability and scalability of these processes are critical for ensuring that researchers worldwide have access to sufficient quantities of these valuable reagents without compromising on quality.

The future prospects for 3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine are bright given its broad applicability across multiple disciplines within chemical biology. As our understanding of biological systems deepens through techniques such as cryo-electron microscopy (cryo-EM) and next-generation sequencing (NGS), there will be increasing opportunities to exploit this compound's unique properties for drug discovery initiatives. Furthermore，the integration with computational chemistry tools promises even more efficient ways to design novel derivatives with enhanced biological activity.

In conclusion,3-(5,5-Dimethyl-1,,3,,2-dioxaborinan-2-yl)pyridine (CAS No.845885-86-1) stands out as a multifunctional compound with significant potential applications in both academic research and industrial settings. Its combination of structural features—such as the dimethyl-substituted dioxaborane unit and the pyridine ring"—makes it an indispensable tool for chemists working on drug development,
biomolecular interactions,
and synthetic methodologies.
With ongoing advancements expected
in chemical biology technologies,
this compound
will undoubtedly play
a pivotal role
in shaping
the future
of medicinal chemistry.

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