Atomfair 2-Chloro-6-hydroxyphenylboronic acid pinacol ester C12H16BClO3 CAS 1451391-17-5

Description

2-Chloro-6-hydroxyphenylboronic acid pinacol ester (CAS No. 1451391-17-5) is a high-purity boronic acid ester derivative designed for advanced synthetic and catalytic applications in organic chemistry and pharmaceutical research. This compound, with the molecular formula C₁₂H₁₆BClO₃, features a stable pinacol boronate group coupled with a chloro-hydroxyphenyl moiety, making it an excellent building block for Suzuki-Miyaura cross-coupling reactions and other transition-metal-catalyzed transformations. Its IUPAC name, 3-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, reflects its precise structural configuration, ensuring reproducibility in complex syntheses. Supplied as a crystalline solid with >95% purity (HPLC), this reagent is rigorously tested for moisture sensitivity and stored under inert conditions to guarantee optimal performance. Ideal for researchers developing novel bioactive compounds, materials, or agrochemicals, it is packaged in amber glass vials with septa to prevent degradation.

Properties

• CAS Number: 1451391-17-5
• Complexity: 279
• IUPAC Name: 3-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
• InChI: InChI=1S/C12H16BClO3/c1-11(2)12(3,4)17-13(16-11)10-8(14)6-5-7-9(10)15/h5-7,15H,1-4H3
• InChI Key: BSFCYZUEPAANES-UHFFFAOYSA-N
• Exact Mass: 254.0881022
• Molecular Formula: C12H16BClO3
• Molecular Weight: 254.52
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C(C=CC=C2Cl)O
• Topological: 38.7
• Monoisotopic Mass: 254.0881022
• Synonyms: 1451391-17-5, 2-Chloro-6-hydroxyphenylboronic acid pinacol ester, 3-CHLORO-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENOL, 2-Chloro-6-hydroxyphenylboronic acid, pinacol ester, MFCD16994238, DTXSID001167346, AKOS027251110, MB15177, BS-30950, SY271978, CS-0174068, D71795, Phenol, 3-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

Application

2-Chloro-6-hydroxyphenylboronic acid pinacol ester is widely employed as a key intermediate in the synthesis of pharmaceuticals, particularly in the construction of biaryl scaffolds via Suzuki-Miyaura coupling. Its orthogonal reactivity enables selective functionalization in multi-step reactions, making it valuable for producing kinase inhibitors and antimicrobial agents. The compound’s phenol group allows for further derivatization, such as etherification or esterification, expanding its utility in medicinal chemistry. Researchers also utilize it in material science to create boron-doped organic electronic materials. Strict handling under anhydrous conditions is recommended to preserve its reactivity.

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