Description

2-Allylphenyl trifluoromethanesulfonate (CAS No. 109586-43-8) is a high-purity, organosulfur compound with the molecular formula C₁₀H₉F₃O₃S. This specialty chemical is widely utilized in organic synthesis, particularly as a versatile electrophile or intermediate in cross-coupling reactions, such as Suzuki-Miyaura and Heck couplings. Its IUPAC name, (2-prop-2-enylphenyl) trifluoromethanesulfonate, reflects its structural composition, featuring an allyl group adjacent to a phenyl ring activated by a trifluoromethanesulfonate (triflate) leaving group. This compound is supplied as a clear to pale-yellow liquid under standard conditions and should be stored in a cool, dry, and inert environment to maintain stability. Ideal for researchers in pharmaceutical, agrochemical, and materials science applications, it is characterized by its high reactivity and compatibility with palladium-catalyzed transformations. Purity is guaranteed via GC/MS and NMR analysis to meet rigorous laboratory standards.

Properties

• CAS Number: 109586-43-8
• Complexity: 356
• IUPAC Name: (2-allylphenyl) trifluoromethanesulfonate
• InChI: InChI=1S/C10H9F3O3S/c1-2-5-8-6-3-4-7-9(8)16-17(14,15)10(11,12)13/h2-4,6-7H,1,5H2
• InChI Key: GOJIIZZUXJZZNC-UHFFFAOYSA-N
• Exact Mass: 266.02244980
• Molecular Formula: C10H9F3O3S
• Molecular Weight: 266.24
• SMILES: C=CCC1=CC=CC=C1OS(=O)(=O)C(F)(F)F
• Topological: 51.8
• Monoisotopic Mass: 266.02244980
• Synonyms: 109586-43-8, 2-Allylphenyl trifluoromethanesulfonate, Trifluoromethanesulfonic Acid 2-(2-Propen-1-yl)phenyl Ester, 1,1,1-Trifluoromethanesulfonic Acid 2-(2-Propen-1-yl)phenyl Ester, starbld0007250, H42096

Application

2-Allylphenyl trifluoromethanesulfonate serves as a key intermediate in the synthesis of complex organic molecules, particularly in palladium-catalyzed cross-coupling reactions to form biaryl or styrenyl derivatives. Its triflate group enhances reactivity in nucleophilic substitution and metal-catalyzed transformations, making it valuable for constructing pharmacophores or functionalized polymers. Researchers also employ it in the development of novel ligands or catalysts due to its allyl-substituted aromatic scaffold.

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