Description

4,4′-Thiodiphthalic anhydride (CAS No. 25884-43-9) is a high-purity organic compound with the molecular formula C₁₆H₆O₆S. This specialized anhydride is widely utilized in advanced polymer synthesis, particularly in the production of thermally stable and chemically resistant polyimides and epoxy resins. Its IUPAC name, 5-[(1,3-dioxo-2-benzofuran-5-yl)sulfanyl]-2-benzofuran-1,3-dione, reflects its unique bifunctional structure, featuring two phthalic anhydride moieties linked by a thioether bridge. This configuration enables exceptional reactivity in polycondensation reactions, making it a valuable monomer for high-performance materials. Our product is rigorously tested to ensure ≥98% purity (HPLC), with low trace metal content, and is supplied as a fine, off-white to pale yellow crystalline powder. Suitable for research and industrial applications, it is packaged under inert gas to maintain stability and shipped with detailed technical documentation, including MSDS, NMR, and HPLC reports.

Properties

• CAS Number: 25884-43-9
• Complexity: 537
• IUPAC Name: 5-(1,3-dioxoisobenzofuran-5-yl)sulfanylisobenzofuran-1,3-dione
• InChI: InChI=1S/C16H6O6S/c17-13-9-3-1-7(5-11(9)15(19)21-13)23-8-2-4-10-12(6-8)16(20)22-14(10)18/h1-6H
• InChI Key: PHCJRSXXXCZFPL-UHFFFAOYSA-N
• Exact Mass: 325.98850908
• Molecular Formula: C16H6O6S
• Molecular Weight: 326.3
• SMILES: C1=CC2=C(C=C1SC3=CC4=C(C=C3)C(=O)OC4=O)C(=O)OC2=O
• Topological: 112
• Monoisotopic Mass: 325.98850908
• Synonyms: 25884-43-9, 4,4′-thiodiphthalic anhydride, 5,5′-Thiobis(isobenzofuran-1,3-dione), 1,3-Isobenzofurandione, 5,5′-thiobis-, SCHEMBL301318, CS-0088673, D74705, EN300-7563575, 4,4 inverted exclamation mark -Bis(phthalic anhydride)sulfide, 5-[(1,3-dioxo-2-benzofuran-5-yl)sulfanyl]-2-benzofuran-1,3-dione, 5-[(1,3-dioxo-1,3-dihydro-2-benzofuran-5-yl)sulfanyl]-1,3-dihydro-2-benzofuran-1,3-dione

Application

4,4′-Thiodiphthalic anhydride serves as a critical monomer in the synthesis of sulfur-containing polyimides, which exhibit enhanced solubility and optical properties compared to traditional polyimides. It is employed in high-temperature adhesives, coatings, and electronic encapsulants due to its thermal stability (up to 400°C). The compound’s thioether linkage also contributes to flame-retardant properties in specialty polymers. Researchers leverage its reactivity in developing advanced composites for aerospace and microelectronics applications.

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