TABLE Some Physical and Thermodynamic Properties of DMC

Density (df) 1.07

Dielectric constant (s25) 3.087

Dipol moment D) 0.91

Solubility H2O (g/100g) 13.9

Azeotropical mixtures With water, alcohols, hydrocarbons

2. DMC is classified as a flammable liquid, smells like methanol, and does not have irritating or mutagenic effects, either by contact or inhalation. Therefore, it can be handled safely without the special precautions required for the poisonous and mutagenic methyl halides and DMS, and extremely toxic phosgene. Some physicochemical properties of DMC are listed in Table 4.2.

3. DMC exhibits a versatile and tunable chemical reactivity that depends on the experimental conditions. In the presence of a nucleophile (Y ), DMC can react either as a methoxycarbonylating or as a methylating agent (Scheme 4.5).10

Although there is not always a clear cutoff between the two pathways of Scheme 4.5, it is generally observed that:

i. At the reflux temperature (T = 90°C), DMC acts primarily as a methoxycarbonylating agent by a BAC2 (bimolecular, base-catalyzed, acyl cleavage, nucleophilic substitution) mechanism where the nucleophile attacks the

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