Description

3-Bromo-4-hydroxyphenylsulfur pentafluoride (CAS No. 1426290-12-1) is a highly specialized organosulfur compound with the molecular formula C₆H₄BrF₅OS. This chemical features a unique pentafluorothio (-SF₅) functional group attached to a brominated phenol scaffold, making it a valuable intermediate in advanced synthetic chemistry and materials science. With its IUPAC name 2-bromo-4-(pentafluoro-lambda6-sulfanyl)phenol, this compound exhibits exceptional reactivity due to the electron-withdrawing nature of the -SF₅ group, which enhances its utility in cross-coupling reactions, pharmaceutical derivatization, and agrochemical synthesis. Provided as a high-purity solid (typically ≥95% by GC/HPLC), it is rigorously tested for consistency and stability under controlled conditions. Ideal for researchers exploring fluorinated building blocks or sulfur-based ligands, this product is packaged under inert gas to ensure longevity and shipped with comprehensive analytical data (NMR, MS).

Properties

• CAS Number: 1426290-12-1
• Complexity: 238
• IUPAC Name: 2-bromo-4-(pentafluoro-lambda6-sulfanyl)phenol
• InChI: InChI=1S/C6H4BrF5OS/c7-5-3-4(1-2-6(5)13)14(8,9,10,11)12/h1-3,13H
• InChI Key: YPWCCOJAIASGTG-UHFFFAOYSA-N
• Exact Mass: 297.90864
• Molecular Formula: C6H4BrF5OS
• Molecular Weight: 299.06
• SMILES: C1=CC(=C(C=C1S(F)(F)(F)(F)F)Br)O
• Topological: 21.2
• Monoisotopic Mass: 297.90864
• Synonyms: 1426290-12-1, 2-Bromo-4-(pentafluorothio)phenol, 3-Bromo-4-hydroxyphenylsulfur pentafluoride, 3-Bromo-4-hydroxyphenylsulphur pentafluoride, 2-bromo-4-(pentafluoro-lambda6-sulfanyl)phenol, SCHEMBL16914498, MFCD23166763, 2-bromo-4-(pentafluoro-|E?-sulfanyl)phenol

Application

3-Bromo-4-hydroxyphenylsulfur pentafluoride serves as a key precursor in the synthesis of SF₅-containing aromatic systems, which are increasingly sought after in medicinal chemistry for their metabolic stability and lipophilicity. Its bromophenol moiety enables participation in Pd-catalyzed cross-coupling reactions (e.g., Suzuki-Miyaura), while the -SF₅ group acts as a bioisostere for trifluoromethyl (-CF₃) in drug design. This compound is also employed in the development of high-performance polymers and liquid crystals, where the -SF₅ group imparts unique dielectric properties. Researchers utilize it to create advanced ligands for catalysis or as a probe in 18F-radiolabeling studies due to its structural analogy to fluorinated biomarkers.

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