Description

2-[N,N-Bis(trifluoromethylsulfonyl)amino]pyridine (CAS No. 145100-50-1) is a high-purity triflating reagent widely used in organic synthesis and pharmaceutical research. This specialized compound features a pyridine core functionalized with bis(trifluoromethylsulfonyl)amino groups, making it an excellent electrophile for introducing triflyl (Tf) moieties. With the molecular formula C₇H₄F₆N₂O₄S₂, it offers exceptional reactivity in nucleophilic substitution reactions, metal-catalyzed cross-coupling, and as a precursor for N-heterocyclic scaffolds. Its trifluoromethylsulfonyl groups enhance thermal stability and electron-withdrawing properties, ideal for constructing complex molecules in medicinal chemistry. Packaged under inert conditions to ensure longevity, this reagent is rigorously tested via HPLC, NMR, and MS to guarantee ≥96% purity. Compatible with anhydrous solvents like THF, DCM, and DMF, it is a must-have for researchers developing advanced materials, ligands, or bioactive compounds.

Properties

• CAS Number: 145100-50-1
• Complexity: 526
• IUPAC Name: 1,1,1-trifluoro-N-(2-pyridyl)-N-(trifluoromethylsulfonyl)methanesulfonamide
• InChI: InChI=1S/C7H4F6N2O4S2/c8-6(9,10)20(16,17)15(5-3-1-2-4-14-5)21(18,19)7(11,12)13/h1-4H
• InChI Key: DXLQEJHUQKKSRB-UHFFFAOYSA-N
• Exact Mass: 357.95166793
• Molecular Formula: C7H4F6N2O4S2
• Molecular Weight: 358.2
• SMILES: C1=CC=NC(=C1)N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F
• Topological: 101
• Monoisotopic Mass: 357.95166793
• Synonyms: 145100-50-1, 2-[N,N-Bis(trifluoromethylsulfonyl)amino]pyridine, 1,1,1-Trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)sulfonyl)methanesulfonamide, N-(2-Pyridyl)bis(trifluoromethanesulfonimide), 2-Pyridyltriflimide, 1,1,1-trifluoro-N-pyridin-2-yl-N-(trifluoromethylsulfonyl)methanesulfonamide, MFCD00191834, 1,1,1-trifluoro-N-(pyridin-2-yl)-N-trifluoromethanesulfonylmethanesulfonamide, Methanesulfonamide, 1,1,1-trifluoro-N-2-pyridinyl-N-[(trifluoromethyl)sulfonyl]-, 2-[N,N-BIS(TRIFLUOROMETHANESULFONYL)AMINO]PYRIDINE, 2-[N,N-BIS(TRIFLUOROMETHYL)SULPHONYLAMINO]PYRIDINE, N,N-Bis(trifluoromethylsulfonyl)-2-pyridylamine, 1,1,1-Trifluoro-N-(pyridin-2-yl)-N-((trifluoro-methyl)sulfonyl)methanesulfonamide, 2-(N,N-bis(trifluoromethylsulfonyl)amino)pyridine, Pyridin-2-amine, N,N-bis(trifluoromethylsulfonyl)-, 1,1,1-trifluoro-N-(2-pyridyl)-N-(trifluoromethylsulfonyl)methanesulfonamide, SCHEMBL306348, C7H4F6N2O4S2, N-(2-PYRIDYL)TRIFLIMIDE, DTXSID50336503, AKOS015890611, CS-W021265, DS-4659, MB00873, SY045604, DB-020296, B1871, ST51006873, bis[(trifluoromethyl)sulfonyl]-2-pyridylamine, EN300-7366614, 2-[N,N-Bis(trifluoromethansulfonyl)amino]pyridine, 2-(N,N-bis(trifluoromethylsulfonyl)amino)-pyridine, 2-[N,N-bis(trifluoro-methanesulfonyl)amino]pyridine, 2-[N,N-bis(trifluoromethyl-sulfonyl)amino]pyridine, N-(2-Pyridyl)bis(trifluoromethanesulfonimide), 96%, N-(2-Pyridyl)bis(trifluoromethanesulfonimide) [Triflating Reagent], Trifluoro-N-(2-pyridinyl)-N-[(trifluoromethyl)sulfonyl]methanesulfonamide #, 1,1,1-trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl) sulfonyl)methanesulfonamide, 1,1,1-Trifluoro-N-(pyridin-2-yl)-N-(trifluoromethanesulfonyl)methanesulfonamide, 1,1,1-trifluoro-N-(pyridin-2-yl)-N-(trifluoromethylsulfonyl) methanesulfonamide, 1,1,1-trifluoro-N-(pyridin-2-yl)-N-(trifluoromethylsulfonyl)methanesulfonamide, 1,1,1-trifluoro-N-(pyridine-2-yl)-N-((trifluoromethyl)sulfonyl)methanesulfonamide, TRIFLUORO-N-PYRIDIN-2-YL-N-[(TRIFLUOROMETHYL)SULFONYL]METHANESULFONAMIDE

This reagent serves as a versatile triflating agent for converting alcohols/phenols to triflates in peptide synthesis and catalyst design. It enables efficient pyridine-directed functionalization in transition metal catalysis (e.g., Pd-catalyzed C-H activation). Applied in electrolyte additives for lithium-ion batteries due to its sulfonylimide stability. Used to synthesize sulfonamide-based pharmaceuticals and agrochemicals. Also employed in polymer science to modify monomer reactivity.

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]
• H335 (97.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (97.9%)

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