Description

3-Pyridyl Trifluoromethanesulfonate (CAS No. 107658-27-5) is a high-purity, organosulfur compound with the molecular formula C₆H₄F₃NO₃S. This reagent, also known as pyridin-3-yl trifluoromethanesulfonate, is a versatile triflate ester widely used in organic synthesis and pharmaceutical research. Its trifluoromethanesulfonate (triflate) group serves as an excellent leaving group, enabling efficient nucleophilic substitution reactions. The compound is characterized by its exceptional reactivity in cross-coupling reactions, such as Suzuki-Miyaura and Negishi couplings, making it invaluable for constructing complex heterocyclic scaffolds. Supplied as a crystalline solid or solution, it is rigorously tested for purity (typically ≥97% by HPLC or GC analysis) and stored under inert conditions to ensure stability. Ideal for researchers in medicinal chemistry, catalysis, and material science.

Properties

• CAS Number: 107658-27-5
• Complexity: 282
• IUPAC Name: 3-pyridyl trifluoromethanesulfonate
• InChI: InChI=1S/C6H4F3NO3S/c7-6(8,9)14(11,12)13-5-2-1-3-10-4-5/h1-4H
• InChI Key: ZRNDSLLIAOLRJS-UHFFFAOYSA-N
• Exact Mass: 226.98639865
• Molecular Formula: C6H4F3NO3S
• Molecular Weight: 227.16
• SMILES: C1=CC(=CN=C1)OS(=O)(=O)C(F)(F)F
• Topological: 64.6
• Monoisotopic Mass: 226.98639865
• Synonyms: 3-Pyridyl Trifluoromethanesulfonate, 107658-27-5, DTXSID50452636, DTXCID40403455, 691-520-2, PYRIDIN-3-YL TRIFLUOROMETHANESULFONATE, 3-Pyridyl Triflate, pyridine-3-triflate, MFCD00799579, SCHEMBL3718580, SCHEMBL6349866, 3-PyridylTrifluoromethanesulfonate, AB9964, AKOS015910975, 3-(Trifluoromethylsulfonyloxy)-pyridine, FP11415, KM-0024, 3-(trifluoromethanesulfonyloxy)-pyridine, DB-262490, CS-0440501, P1860, Trifluoromethanesulfonic Acid 3-Pyridyl Ester, Methanesulfonic acid,1,1,1-trifluoro-,3-pyridinyl ester

Application

3-Pyridyl Trifluoromethanesulfonate is a key intermediate in the synthesis of pharmaceuticals and agrochemicals, particularly for introducing pyridyl motifs via palladium-catalyzed cross-coupling reactions. It is employed in the preparation of kinase inhibitors and other bioactive molecules due to its ability to facilitate C-N and C-C bond formations. The compound’s triflate group also enhances electrophilicity in SN² reactions, enabling efficient functionalization of pyridine derivatives.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Precautionary Statements

• P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)

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