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dimethyl sulfate[‚dī′meth·əl ′səl‚fāt]
the dimethyl ester of sulfuric acid, (CH3)2SO4; a colorless liquid. Melting point, −31.4°C; boiling point, 188. 6°C; density, 1.3283 g/cm3 (20°C); index of refraction n20D. 1.3874. Highly toxic. Dimethyl sulfate is slightly soluble in water (2.8 percent), has limited solubility in hydrocarbons, and is completely miscible with alcohols and ethers. When treated with water it gives methyl sulfate and methanol or methyl ether plus sulfuric acid. In organic synthesis it is used as a methylating agent, for example:
ROH + (CH3)2SO4 → ROCH3
RCOOH + (CH3)2SO4 → RCOOCH3
KCN + (CH3)2SO4 → CH3CN
Dimethyl sulfate is made, for example, by distilling a mixture of CH3OH and 60-percent oleum.