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2-Ethylphenylboronic Acid丨CAS 90002-36-1 Bulk Manufacturer
2-Ethylphenylboronic acid (CAS 90002-36-1), also known as 2-ethylbenzeneboronic acid or (2-ethylphenyl)boronic acid, is an aromatic organoboron compound containing a boronic acid group and an ethyl substituent at adjacent positions on a benzene ring. The boronic acid group serves as a versatile reaction site for carbon–carbon bond formation, while the ortho-ethyl substituent introduces steric bulk and modifies the hydrophobic characteristics of the aromatic ring. This combination makes the compound a useful building block for preparing substituted biaryls, pharmaceutical research intermediates, and specialty aromatic chemicals.
Chemical Identifiers
| InChI | 1S/C8H11BO2/c1-2-7-5-3-4-6-8(7)9(10)11/h3-6,10-11H,2H2,1H3 |
| InChI Key |
QSSPYZOSTJDTTL-UHFFFAOYSA-N |
| Smiles | OB(C1=CC=CC=C1CC)O |
| EC No. | 677-274-9 |
| MDL No. | MFCD02093075 |
| PubChem CID | 4100862 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
2-Ethylphenylboronic acid is used as an organoboron coupling partner in Suzuki–Miyaura reactions. Under suitable palladium-catalyzed conditions, it can react with compatible aryl or heteroaryl halides to produce substituted biaryl and heterobiaryl compounds. This transformation enables the introduction of a 2-ethylphenyl fragment into larger molecular frameworks. The ethyl group adjacent to the boronic acid functionality can create steric hindrance around the reaction site, making catalyst selection, base choice, and reaction conditions important considerations for efficient coupling.
Applications in Medicinal Chemistry
In medicinal chemistry, 2-Ethylphenylboronic acid serves as a building block for preparing aromatic research molecules containing an ortho-ethyl substituent. Alkyl groups can influence molecular lipophilicity, steric interactions, and conformational preferences, which may affect how candidate compounds interact with biological targets. Through suitable cross-coupling reactions, researchers can incorporate the 2-ethylphenyl fragment into molecular libraries and evaluate its influence on physicochemical properties and biological activity. This approach supports lead optimization and structure–activity relationship studies.
Applications in Pharmaceutical Intermediate Synthesis
2-Ethylphenylboronic acid may support pharmaceutical intermediate synthesis requiring alkyl-substituted aromatic structures. The boronic acid functionality enables carbon–carbon bond formation with suitable coupling partners, allowing the preparation of more complex aromatic and heteroaromatic intermediates. The ortho-ethyl substituent provides a defined structural feature that may influence molecular geometry and interactions in downstream compounds. These characteristics make the compound relevant to multistep synthesis and the preparation of specialized pharmaceutical research building blocks.
Applications in Sterically Hindered Biaryl Synthesis
The ortho-ethyl group makes this compound particularly useful for preparing sterically substituted biaryl structures. When the 2-ethylphenyl fragment is connected to another aromatic ring, the adjacent ethyl group may influence rotation around the newly formed aryl–aryl bond. Depending on the substitution pattern of the coupling partner, this can affect molecular conformation and the relative orientation of aromatic rings. Such compounds are useful in research involving conformational control, steric effects, and structure–property relationships.
