Methyl trifluoromethanesulfonate

Chemical properties

clear colourless to yellow liquid

The Uses of Methyl trifluoromethanesulfonate

Methyl trifluoromethanesulfonate is used as a powerful methylating reagent in chemistry. Further, it is used in the conversion of amines to methyl ammonium triflates. In addition, it is also used in Suzuki reaction.

What are the applications of Application

Methyl trifluoromethanesulfonate is a product used as a methylation reagent

General Description

Methyl trifluoromethane sulfonate is a brown liquid. Insoluble in water. (NTP, 1992) This material is a very reactive methylating agent, also known as methyl triflate.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Methyl trifluoromethanesulfonate is sensitive to heat. . Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition Methyl trifluoromethanesulfonate emits toxic fumes.

Fire Hazard

Methyl trifluoromethanesulfonate is combustible.

Toxicology

Methyl trifluoromethanesulfonate is extremely hazardous. All possible precautions should be taken to avoid inhalation or absorption through the skin. This material is extremely destructive to the tissue of the mucous membranes and upper respiratory tract, eyes, and skin. Inhalation may be fatal as a result of spasm, inflammation, and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema. Use in a fume hood. Although there has yet to be a reported human fatality, several cases were reported for methyl fluorosulfonate (LC50 (rat, 1 h) = 5 ppm), and methyl triflate is expected to have similar toxicity based on available evidence.

Purification Methods

Methyl trifluoromethanesulfonate (methyl triflate) [333-27-7] M 164.1, b 97 -97.5o/736mm, 9 9o/~760mm, 100-102o/~760mm, d 4 1.496, n D 1.3238. It is a strong methylating agent but is corrosive and POISONOUS. Fractionate it carefully and collecting the middle fraction (use an efficient fume cupboard) and keep away from moisture. It is a POWERFUL ALKYLATING AGENT and a strong IRRITANT. [IR: Gramstad & Haszeldine J Chem Soc 173 1956 , J Chem Soc 4069 1957 .] Trifluoromethanesulfonic acid (triflic acid) [1493-13-6] M 151.1, boils higher (b 162o/atm), has a pKa of 3.10, and is TOXIC and hygroscopic. [Hansen J Org Chem 30 4322 1965, Kurz & El-Nasr J Am Chem Soc 104 5823 1982, Beilstein 3 IV 34.]