Description

o-Tolyl Trifluoromethanesulfonate (CAS No. 66107-34-4) is a high-purity, organosulfur compound with the molecular formula C₈H₇F₃O₃S. Also known as (2-methylphenyl) trifluoromethanesulfonate, this reagent is widely utilized in organic synthesis and pharmaceutical research due to its excellent reactivity as a triflate ester. Its structure features a trifluoromethanesulfonate group (-OTf) attached to an o-tolyl (2-methylphenyl) ring, making it a versatile electrophile for cross-coupling reactions, such as Suzuki-Miyaura and Heck reactions.

This compound is supplied as a clear to pale-yellow liquid with >98% purity (GC), ensuring optimal performance in demanding synthetic applications. It is moisture-sensitive and should be stored under inert conditions (argon/nitrogen) at 2-8°C. Suitable for use in anhydrous solvents like THF, DCM, and DMF. Hazard statements apply (H314, H290)—handle with appropriate PPE.

Properties

• CAS Number: 66107-34-4
• Complexity: 304
• IUPAC Name: o-tolyl trifluoromethanesulfonate
• InChI: InChI=1S/C8H7F3O3S/c1-6-4-2-3-5-7(6)14-15(12,13)8(9,10)11/h2-5H,1H3
• InChI Key: RBOGJRXPKONDGC-UHFFFAOYSA-N
• Exact Mass: 240.00679974
• Molecular Formula: C8H7F3O3S
• Molecular Weight: 240.20
• SMILES: CC1=CC=CC=C1OS(=O)(=O)C(F)(F)F
• Topological: 51.8
• Monoisotopic Mass: 240.00679974
• Synonyms: o-tolyl Trifluoromethanesulfonate, 811-162-4, 66107-34-4, Methanesulfonic acid, trifluoro-, 2-methylphenyl ester, (2-methylphenyl) trifluoromethanesulfonate, o-tolyl triflate, 2-Methylphenyl trifluoromethanesulfonate, 2-Tolyl trifluoromethanesulfonate, o-tolyltriflate, 2-Cresol triflate, MFCD29089375, 2-Methylphenyl triflate, o-tolylTrifluoromethanesulfonate, SCHEMBL2984151, SCHEMBL5366474, DTXSID10341279, AKOS027253000, 2-Methylphenyl trifluoromethanesulfonate #, AS-69597, Trifluoromethanesulfonic Acid o-Tolyl Ester, CS-0197359, T3357, T72793

Application

o-Tolyl Trifluoromethanesulfonate serves as a key intermediate in palladium-catalyzed coupling reactions to construct biaryl scaffolds for drug discovery. It is particularly valuable in synthesizing agrochemicals and liquid crystal materials due to its electron-withdrawing triflate group. Researchers also employ it as a precursor for chiral ligand synthesis in asymmetric catalysis. Its stability under acidic conditions makes it suitable for late-stage functionalization in complex molecule synthesis.

Safety and Hazards

GHS Hazard Statements

• H302+H312+H332 (100%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
• 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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