Description

2-Chlorophenyl Trifluoromethanesulfonate (CAS No. 66107-36-6) is a high-purity organofluorine compound with the molecular formula C₇H₄ClF₃O₃S, widely utilized in advanced synthetic chemistry and pharmaceutical research. This triflate ester derivative is characterized by its exceptional reactivity as an electrophile, making it a versatile reagent for cross-coupling reactions, nucleophilic substitutions, and as a precursor in the synthesis of complex organic molecules. Its trifluoromethanesulfonyl (triflyl) group enhances leaving-group ability, enabling efficient transformations under mild conditions. Supplied as a clear to pale yellow liquid, it is rigorously tested for purity (typically ≥95% by GC) and stored under inert conditions to ensure stability. Ideal for Suzuki-Miyaura, Heck, and Buchwald-Hartwig couplings, this compound is a staple in medicinal chemistry, agrochemical development, and material science applications. Compatible with anhydrous solvents like THF, DMF, and DCM, it is packaged in amber glass vials under nitrogen to prevent degradation.

Properties

• CAS Number: 66107-36-6
• Complexity: 308
• IUPAC Name: (2-chlorophenyl) trifluoromethanesulfonate
• InChI: InChI=1S/C7H4ClF3O3S/c8-5-3-1-2-4-6(5)14-15(12,13)7(9,10)11/h1-4H
• InChI Key: KTLNEJOQAOFUTO-UHFFFAOYSA-N
• Exact Mass: 259.9521773
• Molecular Formula: C7H4ClF3O3S
• Molecular Weight: 260.62
• SMILES: C1=CC=C(C(=C1)OS(=O)(=O)C(F)(F)F)Cl
• Topological: 51.8
• Monoisotopic Mass: 259.9521773
• Synonyms: 2-Chlorophenyl trifluoromethanesulfonate, 66107-36-6, DTXSID50342402, DTXCID70293482, 678-361-4, ktlnejoqaofuto-uhfffaoysa-n, 2-Chlorophenyl Triflate, (2-chlorophenyl) trifluoromethanesulfonate, MFCD07784322, Trifluoromethanesulfonic Acid 2-Chlorophenyl Ester, SCHEMBL5599422, 2-Chlorophenyltrifluoromethanesulfonate, DB-228034, C2326, CS-0182177, T71189, Methanesulfonic acid,1,1,1-trifluoro-,2-chlorophenyl ester

2-Chlorophenyl Trifluoromethanesulfonate is primarily employed as a key intermediate in palladium-catalyzed cross-coupling reactions to construct biaryl scaffolds in drug discovery. Its triflate group facilitates efficient arylations in Suzuki and Negishi couplings, enabling the synthesis of tailored pharmaceutical candidates. Researchers also exploit its reactivity in polymer chemistry to introduce chlorophenyl motifs into functional materials. The compound’s moisture sensitivity necessitates handling under inert atmospheres (e.g., glovebox) for optimal results.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P321, P330, P332+P317, P337+P317, P362+P364, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• Acute Tox. 4 (100%)

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