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High Quality Dibenzothiophene-2-boronic Acid丨CAS 668983-97-9
Dibenzothiophene-2-boronic acid (CAS 668983-97-9) is a sulfur-containing aromatic boronic acid featuring a dibenzothiophene framework with a boronic acid group at the 2-position. Its rigid, fused aromatic structure and organoboron functionality make it a useful building block for organic synthesis, electronic materials research, and specialty chemical development. The dibenzothiophene unit is frequently investigated in organic electronic materials because of its structural rigidity and electronic characteristics, while the boronic acid group enables carbon–carbon bond formation through suitable cross-coupling reactions. This combination makes the compound particularly relevant to the preparation of advanced aromatic molecules and functional organic materials.
Chemical Identifiers
| InChI | InChI=1S/C12H9BO2S/c14-13(15)8-5-6-12-10(7-8)9-3-1-2-4-11(9)16-12/h1-7,14-15H |
| InChI Key |
CSLSCVHILGCSTE-UHFFFAOYSA-N |
| Smiles | B(C1=CC2=C(C=C1)SC3=CC=CC=C32)(O)O |
| EC No. | 688-282-7 |
| MDL No. | MFCD01318982 |
| PubChem CID | 2794660 |
Applications
Applications in Antifungal Treatment
The boronic acid functionality of Dibenzothiophene-2-boronic acid enables its use in Suzuki–Miyaura cross-coupling reactions. Under appropriate palladium-catalyzed conditions, the compound can react with compatible aryl or heteroaryl halides and pseudohalides to form new carbon–carbon bonds. This reaction provides a practical route for introducing a dibenzothiophen-2-yl fragment into complex aromatic and heteroaromatic structures. Such transformations are particularly useful in the synthesis of conjugated molecules, specialty organic intermediates, and compounds designed for electronic materials research.
Applications in Medicinal Chemistry
In medicinal chemistry, Dibenzothiophene-2-boronic acid may be used as a building block for preparing sulfur-containing aromatic compounds and exploring structure–activity relationships. The dibenzothiophene framework provides a rigid, hydrophobic aromatic unit, while the boronic acid group supports its incorporation into more complex molecular structures. Researchers may investigate derivatives containing this fragment to evaluate the influence of fused sulfur heterocycles on physicochemical properties and molecular interactions. Its suitability for pharmaceutical research depends on the intended target structure and biological application.
Applications in OLED Materials Research
Dibenzothiophene-2-boronic acid is a useful intermediate for synthesizing organic compounds investigated in organic light-emitting diode (OLED) technology. Dibenzothiophene-containing structures are explored in the development of host materials, charge-transport materials, and other functional components of OLED devices. Through suitable coupling reactions, this compound can be incorporated into larger aromatic frameworks to investigate energy levels, charge-transport characteristics, thermal properties, and device performance. Its rigid sulfur-containing aromatic structure provides a valuable molecular fragment for designing specialized electronic materials.
Applications in Specialty Organic Synthesis
Beyond electronic materials research, Dibenzothiophene-2-boronic acid is useful in specialty organic synthesis involving fused heteroaromatic building blocks. Its boronic acid functionality supports the construction of carbon–carbon bonds, while the dibenzothiophene structure contributes a defined sulfur-containing aromatic fragment. This combination enables the preparation of substituted dibenzothiophene derivatives, complex biaryl compounds, and advanced organic intermediates. It may also support molecular library development and synthetic methodology studies involving heteroaromatic coupling chemistry.
