1-Dibenzofuranylboronic acid
[CAS# 162607-19-4]

Identification

• Classification: Organic raw materials >> Organoboron compounds
• Name: 1-Dibenzofuranylboronic acid
• Synonyms: dibenzofuran-1-ylboronic acid
• Molecular Formula: C₁₂H₉BO₃
• Molecular Weight: 212.01
• CAS Registry Number: 162607-19-4
• EC Number: 829-640-6
• SMILES: B(C1=C2C3=CC=CC=C3OC2=CC=C1)(O)O

Properties

• Solubility: Insoluble (3.6E^-4 g/L) (25 °C), Calc.^*
• Density: 1.34±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.701, Calc.^*
• Boiling Point: 438.5±37.0 °C (760 mmHg), Calc.^*
• Flash Point: 219.0±26.5 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P264-P264+P265-P270-P280-P301+P317-P302+P352-P305+P351+P338-P321-P330-P332+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

1-Dibenzofuranylboronic acid is an organic compound that consists of a boronic acid group attached to a dibenzofuran ring system. It is a member of the class of boronic acids, which are characterized by the presence of a boron atom bonded to a hydroxyl group and an organic substituent. This compound is used primarily as an intermediate in the synthesis of more complex organic molecules, particularly in the field of organic electronics and materials science.

The compound is synthesized through a variety of methods, typically involving the direct coupling of dibenzofuran derivatives with boronic acid or through the incorporation of the boronic group onto a suitable precursor. The introduction of the boronic acid group onto the dibenzofuran ring system enhances the compound’s reactivity and versatility in subsequent chemical reactions. Boronic acids, such as 1-dibenzofuranylboronic acid, are known to form reversible covalent bonds with certain compounds, a feature that makes them highly valuable in chemical synthesis and catalysis.

1-Dibenzofuranylboronic acid is particularly significant in Suzuki-Miyaura coupling reactions, which are widely employed in organic chemistry to form carbon-carbon bonds. This reaction is essential for the construction of complex organic molecules, especially in the synthesis of polycyclic aromatic hydrocarbons, organic semiconductors, and other advanced materials. In addition, 1-dibenzofuranylboronic acid is used in the synthesis of various bioactive molecules and natural products. The versatility and stability of boronic acid groups enable their use in the design of molecules with specific properties for pharmaceuticals and other chemical applications.

Another application of 1-dibenzofuranylboronic acid is in the field of organic optoelectronic devices, such as organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs). Its structure allows for favorable interactions with other organic materials, making it a useful component in the design of semiconducting materials that can be incorporated into electronic devices.

In summary, 1-dibenzofuranylboronic acid is an important boronic acid derivative used primarily in organic synthesis, especially in reactions that require the formation of carbon-carbon bonds. Its applications span from the creation of complex organic molecules and pharmaceuticals to the development of organic electronic materials, underscoring its importance in various fields of chemical research and industrial production.

References

2023. Redox-neutral ipso/ortho alkenylcyanation of (hetero)arylboronic acid enabled by 1,4-rhodium migration and fragmentation. Science China Chemistry, 66(10).
DOI: 10.1007/s11426-023-1645-x