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3-Chloro-4-isopropoxyphenylboronic acid (CAS 480438-56-0) is a substituted aromatic boronic acid featuring a chlorine atom at the 3-position, an isopropoxy group at the 4-position, and a boronic acid functional group attached to the benzene ring. Its combination of halogen, alkoxy, and boronic acid functionalities makes it a useful building block for organic synthesis, medicinal chemistry, and pharmaceutical intermediate development. The boronic acid group is particularly valuable in palladium-catalyzed cross-coupling reactions, allowing researchers to construct carbon–carbon bonds and prepare structurally diverse aromatic compounds.
Chemical Identifiers
| InChI | InChI=1S/C9H12BClO3/c1-6(2)14-9-4-3-7(10(12)13)5-8(9)11/h3-6,12-13H,1-2H3 |
| InChI Key | PJBWTULFEPFOEB-UHFFFAOYSA-N |
| Smiles | B(C1=CC(=C(C=C1)OC(C)C)Cl)(O)O |
| EC No. | 895-319-2 |
| MDL No. | MFCD04974065 |
| PubChem CID | 3382467 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
3-Chloro-4-isopropoxyphenylboronic acid is suitable for use in Suzuki–Miyaura cross-coupling reactions, an important synthetic method for constructing biaryl and other aryl-containing structures. Under appropriate catalytic conditions, the boronic acid group can react with suitable organic halides or pseudohalides to form new carbon–carbon bonds. The chlorine and isopropoxy substituents remain useful structural features in the resulting molecules, depending on the reaction conditions. This makes the compound valuable for preparing substituted aromatic intermediates and developing complex organic structures.
Applications in Medicinal Chemistry
In medicinal chemistry, 3-Chloro-4-isopropoxyphenylboronic acid serves as a building block for synthesizing substituted aromatic compounds and evaluating structure–activity relationships. The chlorine substituent can influence electronic and steric properties, while the isopropoxy group introduces an ether functionality that may affect lipophilicity and molecular interactions. Researchers can incorporate this aromatic fragment into candidate molecules to investigate how specific substitution patterns influence their physicochemical properties and biological activity.
Applications in Pharmaceutical Intermediate Synthesis
This compound may be used in the preparation of pharmaceutical research intermediates requiring a 3-chloro-4-isopropoxyphenyl structural unit. Its boronic acid functionality provides a practical route for introducing this substituted aromatic ring into more complex molecular frameworks through compatible coupling reactions. It can support multistep synthetic strategies used in pharmaceutical discovery and process development, where reliable access to structurally defined intermediates is important.
Applications in Specialty Organic Synthesis
Beyond pharmaceutical research, 3-Chloro-4-isopropoxyphenylboronic acid can support the synthesis of specialty organic compounds and functionalized aromatic materials. Its substituted phenyl structure offers opportunities for constructing molecular libraries, exploring aromatic substitution effects, and preparing compounds with tailored structural characteristics. The compound may also be useful in research involving advanced organic intermediates, depending on the target structure and selected reaction pathway.
