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Bulk Inquiry 4-(Trimethylsilyl)phenylboronic Acid丨CAS 17865-11-1
4-(Trimethylsilyl)phenylboronic acid (CAS 17865-11-1) is a functionalized aromatic boronic acid featuring a trimethylsilyl group at the para-position of the benzene ring and a boronic acid functionality. Its combination of organoboron and organosilicon structural features makes it a useful building block for organic synthesis, medicinal chemistry, and specialty chemical research. The boronic acid group supports carbon–carbon bond formation through suitable cross-coupling reactions, while the trimethylsilyl substituent provides an additional structural feature for molecular design and subsequent synthetic transformations.
Chemical Identifiers
| InChI | InChI=1S/C9H15BO2Si/c1-13(2,3)9-6-4-8(5-7-9)10(11)12/h4-7,11-12H,1-3H3 |
| InChI Key | NRPZMSUGPMYBCQ-UHFFFAOYSA-N |
| Smiles | B(C1=CC=C(C=C1)[Si](C)(C)C)(O)O |
| EC No. | 672-616-3 |
| MDL No. | MFCD00093348 |
| PubChem CID | 1710 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
4-(Trimethylsilyl)phenylboronic acid can be used in Suzuki–Miyaura cross-coupling reactions to prepare substituted biaryl compounds and other aromatic structures. Under appropriate palladium-catalyzed conditions, the boronic acid group reacts with compatible organic halides or pseudohalides to form new carbon–carbon bonds. The para-trimethylsilyl substituent may be retained in the resulting products when suitable reaction conditions are selected. This makes the compound useful for introducing a trimethylsilyl-substituted phenyl group into more complex molecular frameworks.
Applications in Medicinal Chemistry
In medicinal chemistry, 4-(Trimethylsilyl)phenylboronic acid may serve as a building block for preparing aromatic analogs and investigating structure–activity relationships. The trimethylsilyl group introduces a relatively bulky, hydrophobic substituent that can influence steric characteristics and molecular interactions. Researchers may incorporate this structural feature into suitable compounds to evaluate how organosilicon substitution affects physicochemical properties and biological activity. Its boronic acid functionality also supports the efficient construction of substituted aromatic frameworks during compound library development.
Applications in Pharmaceutical Intermediate Synthesis
This compound may support pharmaceutical research and intermediate synthesis involving substituted aromatic building blocks. The boronic acid group provides a route for introducing the 4-(trimethylsilyl)phenyl fragment into selected target structures through compatible coupling reactions. Depending on the synthetic strategy, the trimethylsilyl group may be retained or subjected to further transformations under appropriately selected conditions. Its suitability for a particular pharmaceutical research route depends on the target structure, reaction compatibility, and required product specifications.
Applications in Specialty Organic Synthesis
4-(Trimethylsilyl)phenylboronic acid is useful in specialty organic synthesis where both aromatic boronic acid reactivity and organosilicon functionality are relevant. It can support the preparation of substituted biaryls, functionalized aromatic intermediates, and structurally diverse research compounds. The combination of boron- and silicon-containing functional groups provides opportunities for designing multistep synthetic routes and investigating the chemical behavior of organosilicon-substituted aromatic molecules.
