methyl trifluoromethanesulfonate

• ChemBase ID: 8489
• Molecular Formular: C2H3F3O3S
• Molecular Mass: 164.1036296
• Monoisotopic Mass: 163.97549962
• SMILES: S(=O)(=O)(C(F)(F)F)OC
• Canonical SMILES: COS(=O)(=O)C(F)(F)F
• InChI: InChI=1S/C2H3F3O3S/c1-8-9(6,7)2(3,4)5/h1H3
• InChIKey: OIRDBPQYVWXNSJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl trifluoromethanesulfonate
• IUPAC Traditional name: triflate ester
• Synonyms: Methyl trifluoromethanesulfonate; Methyl triflate; Methyl trifluoromethanesulphonate 98%; Trifluoromethanesulfonic acid, methyl ester; Triflic acid, methyl ester, methyl triflate; Methyl trifluoromethansulfonate; Methyl trifluoromethanesulfonate; 三氟甲基磺酸甲酯; 三氟甲磺酸甲酯

Database IDs

• CAS Number: 333-27-7
• EC Number: 206-371-7
• MDL Number: MFCD00000409
• Beilstein Number: 774772
• PubChem SID: 160971796; 24850067
• PubChem CID: 9526
• Chemspider ID: 9153
• Wikipedia Title: Methyl_trifluoromethansulfonate

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.5259978
• LogD (pH = 7.4): 1.5259978
• Log P: 1.5259978
• Molar Refractivity: 21.4642 cm^3
• Polarizability: 9.433094 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Hydrolyzes in water
• Apperance: Colourless Liquid
• Melting Point: -64 °C; -64°C
• Boiling Point: 100 °C; 100-102°C; 94-102°C; 94-99 °C(lit.)
• Flash Point: 100 °F; 100.4 °F; 38 °C; 38°C; 38°C
• Density: 1.45; 1.45 g/mL at 25 °C(lit.); 1.450; 1.496 g/mL
• Refractive Index: 1.326; n20/D 1.326(lit.); n20/D 1.327
• Hydrophobicity(logP): 1.631
• Viscosity: ? cP at ?°C

Safety Information

• Storage Warning: Corrosive/Flammable/Air Sensitive/Moisture Sensitive/Store under Argon/Keep Cold; MOISTURE SENSITIVE, TOXIC, CORROSIVE
• European Hazard Symbols: Corrosive (C)
• UN Number: 2920
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2
• Risk Statements: 10-34; R10R34
• Safety Statements: 26-36/37/39-45; S26S36/37/39S45
• TSCA Listed: true
• GHS Pictograms: GHS02; GHS05
• GHS Signal Word: Danger
• Main Hazard: Corrosive
• GHS Hazard statements: H226-H314
• GHS Precautionary statements: P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2920 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); ≥98%; ≥98.0% (GC); 95%; 97%; 98.0%
• Grade: purum
• Linear Formula: CF3SO2OCH3

DETAILS

Sigma Aldrich - 164283

Application
Shown to be the most effective monomethylating agent in reactions with potassium enolates.1
Useful methylation reagent for the conversion of amines to methyl ammonium triflates.
Packaging
10, 50 g in ampule

Sigma Aldrich - 18503

General description
Shown to be the most effective monomethylating agent in reactions with potassium enolates.Useful methylation reagent for the conversion of amines to methyl ammonium triflates.

Sigma Aldrich - 91736

Other Notes
Extremely reactive methylating agent which is about 104 to 105 more reactive than methyl tosylate and methyl iodide1,2; review3; O-methylation of carbohydrates4; N-methylation of amino acids5