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Bulk Order 4,4,5,5-Tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane丨CAS 190788-59-1
4,4,5,5-Tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane (CAS 190788-59-1), also known as 2-nitrophenylboronic acid pinacol ester, is an aromatic organoboron compound containing a pinacol boronate ester group and an ortho-nitro substituent on a benzene ring. The compound combines the synthetic utility of a protected boronic acid with the electronic and chemical characteristics of an aromatic nitro group. Its boronate ester functionality enables carbon–carbon bond formation through suitable cross-coupling reactions, while the nitro group provides an additional site for chemical transformation. These features make it a useful intermediate for medicinal chemistry, pharmaceutical intermediate synthesis, nitrogen-containing heterocyclic compounds, and specialty organic synthesis.
Chemical Identifiers
| InChI |
1S/C12H16BNO4/c1-11(2)12(3,4)18-13(17-11)9-7-5-6-8-10(9)14(15)16/h5-8H,1-4H3 |
| InChI Key | VLJYUDGCEKORNG-UHFFFAOYSA-N |
| Smiles | O=[N+](C1=CC=CC=C1B(OC2(C)C)OC2(C)C)[O-] |
| EC No. | 681-615-7 |
| MDL No. | MFCD02179447 |
| PubChem CID | 3699568 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
4,4,5,5-Tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane is useful in Suzuki–Miyaura cross-coupling reactions for preparing substituted biaryl and aryl–heteroaryl compounds. Under optimized palladium-catalyzed conditions, the pinacol boronate ester group can react with compatible aryl or heteroaryl halides to form new carbon–carbon bonds. This transformation enables the introduction of a 2-nitrophenyl fragment into more complex molecular structures. The ortho-nitro group may influence reaction efficiency through steric and electronic effects, making catalyst selection and reaction optimization important.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound serves as a building block for preparing aromatic research molecules containing nitrogen-based functional groups. The nitro substituent can be converted into an amino group under suitable reduction conditions, providing access to substituted aniline derivatives. These intermediates are widely used in the preparation of pharmaceutical research compounds and molecular libraries. The pinacol boronate functionality enables the construction of diverse aromatic frameworks before further modification of the nitrogen-containing group.
Applications in Pharmaceutical Intermediate Synthesis
4,4,5,5-Tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane may support pharmaceutical intermediate synthesis involving substituted aromatic and heteroaromatic structures. Through suitable cross-coupling reactions, the compound can be incorporated into larger molecular frameworks while retaining the nitro group for subsequent transformation. Reduction of the nitro substituent can produce an amino-functionalized aromatic intermediate suitable for further reactions, including amide formation, sulfonamide synthesis, and selected cyclization processes. This sequential approach provides flexibility in multistep synthesis.
Applications in Nitrogen-Containing Heterocyclic Synthesis
The ortho-nitro substitution pattern makes this compound particularly relevant to the preparation of nitrogen-containing heterocyclic structures. Following suitable cross-coupling reactions, the nitro group may be reduced to an amino group, generating intermediates capable of undergoing intramolecular cyclization or condensation reactions. Depending on the additional functional groups present, these transformations may provide routes to carbazole-related, benzimidazole-related, or other fused nitrogen-containing frameworks. Such structures are investigated in medicinal chemistry and functional materials research.
