Methanesulfonyl chloride

Chemical properties

Colorless to yellow liquid

Chemical properties

Pale yellow corrosive liquid. Unpleasant, pungent odor.

The Uses of Methanesulfonyl chloride

Methanesulfonyl chloride is used as a reagent for conversion of alcohols to mesylate esters such as methanesulfonate, which is an intermediate in substitution reactions, elimination reactions, reductions, and rearrangement reactions viz. Beckmann rearrangement. It is an electrophile and acts as a source of CH3SO2+ group. It is also used to prepare beta-chloro sulfones, methanesulfonamide and heterocyclic compounds containing five membered sultones.

The Uses of Methanesulfonyl chloride

To a solution of the SM (300 mg, 2.30 mmol) in DCM (6 mL) at 0 C was added TEA (0.64 mL, 4.6 mmol) followed by MeSO2Cl (0.21 mL, 2.76 mmol). The reaction mixture was stirred at 0 C for 30 min, then was allowed to warm to RT over 2 h. The mixture was quenched with H2O (10 mL) and extracted with DCM (2 x 20 mL). The combined organics were washed with H2O (20 mL), brine (20 mL), dried (Na2SO4), and concentrated. The resulting material was purified by silica gel column chromatography (35% EtOAc/hexane) to provide the product as a colorless gum. [310 mg, 64%]

The Uses of Methanesulfonyl chloride

In the synthesis of photographic and agricultural chemicals, pharmaceutical intermediates. As a stabilizer; catalyst; curing and chlorinating agent; precursor to methanesulfonic acid.

The Uses of Methanesulfonyl chloride

Methanesulfonyl chloride can be used for the mesylation of primary alcohols to synthesize the corresponding methanesulfonates. It may also be used for the conversion of amines to the corresponding sulfonamides.

General Description

A pale yellow corrosive liquid. More dense than water and insoluble in water. Very toxic by ingestion, inhalation, or skin absorption.

Reactivity Profile

Methanesulfonyl chloride reacts vigorously with water, steam, alkali, methylformamide. Emits toxic fumes of chloride and oxides of sulfur when heated to decomposition. A dangerous storage hazard. Reacts explosively with dimethyl sulfoxide [Buckley, A., J. Chem. Educ., 1965, 42, p. 674]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Health Hazard

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

Potential Exposure

Chemical intermediate in various industries including pesticides, flame retardants, pharmaceuticals, plastics. A solvent, curing agent, and chemical stabilizer. Laboratory chemical.

Shipping

UN3246 Methanesulfonyl chloride, Hazard Class 6.1; Labels: 6.1-Poison Inhalation Hazard, 8-Corrosive material, Inhalation Hazard Zone B.

Purification Methods

Distil the sulfonyl chloride from P2O5 under vacuum. It is a strong IRRITANT.[Beilstein 4 IV 27.]

Incompatibilities

Vapors may form explosive mixture with air. Slowly reacts with water, releasing toxic and corrosive hydrogen chloride gas. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, DMSO, ethers, strong acids, strong bases.

Waste Disposal

Use a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed