Chemical Properties
Methyl carbamate is a white, adhesive crystal. It is highly soluble in water, as well as in ethanol, acetone, and other organic solvents.
Uses
Methyl carbamate was used in the synthesis of protected aminocyclopropanes.
Definition
ChEBI: Methyl carbamate is a carbamate ester resulting from the formal condensation of the carboxy group of carbamic acid with methanol.
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.
General Description
Methyl carbamate appears as white to Almost white powder to crystal. It an intermediate in the manufacture of dimethylol methyl carbamate-based resins, which are used in the textile industry as durable-press fabric finishes for polyester/cotton blends.
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.]
