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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