Description

2-Methoxyphenyl Trifluoromethanesulfonate (CAS No. 59099-58-0) is a high-purity, organosulfur compound with the molecular formula C₈H₇F₃O₄S. This specialized reagent is widely utilized in organic synthesis, particularly as a versatile triflate ester intermediate for nucleophilic substitution reactions, cross-coupling reactions, and as a protecting group in complex molecular architectures. Its IUPAC name is (2-methoxyphenyl) trifluoromethanesulfonate, and it is characterized by its clear to pale-yellow liquid appearance under standard conditions. With a molecular weight of 256.20 g/mol, this compound is rigorously tested for purity (typically ≥95-98% by GC or HPLC) and is supplied in moisture-resistant packaging to ensure stability. Ideal for researchers in pharmaceuticals, agrochemicals, and materials science, it is handled under inert conditions to prevent degradation. Synonyms include DTXSID00472465 and DTXCID40423279.

Properties

• CAS Number: 59099-58-0
• Complexity: 319
• IUPAC Name: (2-methoxyphenyl) trifluoromethanesulfonate
• InChI: InChI=1S/C8H7F3O4S/c1-14-6-4-2-3-5-7(6)15-16(12,13)8(9,10)11/h2-5H,1H3
• InChI Key: RCDZTJFBROIDKD-UHFFFAOYSA-N
• Exact Mass: 256.00171436
• Molecular Formula: C8H7F3O4S
• Molecular Weight: 256.20
• SMILES: COC1=CC=CC=C1OS(=O)(=O)C(F)(F)F
• Topological: 61
• Monoisotopic Mass: 256.00171436
• Synonyms: 2-methoxyphenyl trifluoromethanesulfonate, 59099-58-0, DTXSID00472465, DTXCID40423279, 811-831-0, Methanesulfonic acid, trifluoro-, 2-methoxyphenyl ester, 2-Methoxyphenyl trifluoromethanesulphonate, (2-methoxyphenyl) trifluoromethanesulfonate, 2-Methoxyphenyl Triflate, MFCD25541795, SCHEMBL5599606, RCDZTJFBROIDKD-UHFFFAOYSA-N, AKOS030228752, 2-methoxyphenyltrifluoromethanesulfonate, AS-69899, CS-0197305, M2792, T72670, Trifluoromethanesulfonic Acid 2-Methoxyphenyl Ester

Application

2-Methoxyphenyl Trifluoromethanesulfonate is a key reagent in palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Heck, or Stille couplings) due to its excellent leaving group properties. It serves as a precursor for introducing the 2-methoxyphenyl moiety into complex molecules in pharmaceutical synthesis, such as in the development of kinase inhibitors or GPCR-targeted drugs. Additionally, it is employed in asymmetric catalysis and as a protecting group for phenols in multistep organic transformations.

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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