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4-(Hydroxymethyl)benzeneboronic acid丨CAS 59016-93-2 Manufacturer
4-(Hydroxymethyl)benzeneboronic acid, CAS 59016-93-2, is a functionalized aromatic boronic acid featuring both a boronic acid group and a hydroxymethyl group on a benzene ring. This combination of reactive functionalities makes it a useful building block in organic synthesis, particularly for the preparation of structurally diverse molecules and advanced intermediates. The boronic acid group participates in a range of boron-mediated transformations, while the hydroxymethyl group provides an additional site for chemical modification. Its bifunctional structure offers synthetic flexibility for researchers developing pharmaceutical intermediates, specialty chemicals, and functional organic materials.
Chemical Identifiers
| InChI | 1S/C7H9BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4,9-11H,5H2 |
| InChI Key | PZRPBPMLSSNFOM-UHFFFAOYSA-N |
| Smiles | C1=C(C=CC(=C1)CO)B(O)O |
| EC No. | 672-927-4 |
| MDL No. | MFCD00792672 |
| PubChem CID | 2734706 |
Applications
Applications in Functional Molecule Development
The coexistence of boronic acid and hydroxymethyl groups makes this compound useful in multi-step organic synthesis. The hydroxymethyl group can undergo transformations such as oxidation, esterification, etherification, and other derivatization reactions, depending on the reaction conditions and protecting-group strategy. These modifications allow chemists to introduce different functional groups while retaining or subsequently utilizing the boronic acid moiety. This versatility is beneficial when designing molecular scaffolds with specific structural and functional requirements.
Applications in Pharmaceutical Intermediate Synthesis
The compound is a valuable building block for medicinal chemistry and pharmaceutical intermediate development. Its aromatic boronic acid functionality can be used in palladium-catalyzed Suzuki–Miyaura cross-coupling reactions with suitable organic halides or related electrophiles, enabling the formation of new carbon–carbon bonds. This provides access to biaryl and other aryl-containing structures that are frequently encountered in pharmaceutical research. Meanwhile, the hydroxymethyl substituent offers an additional functional handle for subsequent transformations, supporting the preparation of more complex molecular structures and customized synthetic intermediates.
Applications in Advanced Organic Synthesis
4-(Hydroxymethyl)benzeneboronic acid can support the synthesis of substituted aromatic compounds through cross-coupling chemistry and related organoboron transformations. It may serve as a starting material for preparing more elaborate aromatic building blocks, including compounds with extended conjugation or multiple functional groups. Its two distinct reactive sites provide opportunities for sequential or orthogonal functionalization, making it relevant to synthetic route development, reaction optimization, and the preparation of research-scale intermediates.
Applications in Specialty Chemicals and Materials Research
Beyond pharmaceutical chemistry, this compound may be explored in the development of specialty organic molecules and functional materials. The aromatic framework provides structural stability, while the hydroxymethyl group can be modified to introduce linkers or other functional units. Its boronic acid functionality also offers access to boron-containing derivatives and coupling products. These characteristics make it a useful candidate for research involving functional aromatic compounds, molecular building blocks, and customized material intermediates.
