Methyl carbamate

Preparation

Methyl carbamate was synthesized by the following preparation. MDI (5.00 g,0.020mol) and 100 ml of dried acetone were weighed into a Ng-filled three-neck flask.Methanol (5 g, an excess amount) is added dropwise to the stirred MDI solution in the flask,and then the solution was heated to 56 C. After 24 hrs， the reaction mixture was cooled down to room temperature and evaporated to give a crude solid at about 100% yield. The following recrystallization procedure gave 3.1 g of a white solid (0.012 mol，60% yield). The disappearance of FT-IR stretching band of the isocyanate group (-N=C=O, 2280 cm') confirmed that the reaction was complete.

Definition

ChEBI: Methyl carbamate is a carbamate ester resulting from the formal condensation of the carboxy group of carbamic acid with methanol.

General Description

White crystals.

Air & Water Reactions

Water soluble.

Reactivity Profile

Methyl carbamate is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.

Fire Hazard

Flash point data for Methyl carbamate are not available; however, Methyl carbamate is probably combustible.

Safety Profile

Poison by ingestion and intraperitoneal routes. Questionable carcinogen with experimental carcinogenic and tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also CARBAMATES.

Purification Methods

Crystallise the carbamate from *benzene or distil it. [Beilstein 3 H 21.]