N-Methylformamide

Skeletal structure of N-Methylformamide

N-Methylformamide (NMF) is an organic compound with the formula CH₃NHCHO. It is a colorless liquid that is used as a solvent and reagent in various chemical reactions. N-Methylformamide is a derivative of formamide, where one hydrogen atom is replaced by a methyl group.

Structure and Properties

3D ball-and-stick model of N-Methylformamide

N-Methylformamide is a simple amide with a planar structure due to the partial double bond character of the carbon-nitrogen bond. This partial double bond character is a result of resonance between the lone pair on the nitrogen and the carbonyl group. The resonance structures can be depicted as follows:

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Resonance structures of N-Methylformamide

The presence of the methyl group makes N-Methylformamide more hydrophobic than formamide, but it still retains significant hydrophilic properties due to the amide group. It has a boiling point of approximately 199 °C and is miscible with water and most organic solvents.

Synthesis

N-Methylformamide can be synthesized by the reaction of methylamine with formic acid or its derivatives. The reaction typically involves the formation of an intermediate formate ester, which then undergoes nucleophilic attack by the amine to form the amide.

Applications

N-Methylformamide is used primarily as a solvent in the chemical industry. Its ability to dissolve a wide range of compounds makes it useful in the synthesis of pharmaceuticals, polymers, and agrochemicals.

In addition to its role as a solvent, N-Methylformamide is also used as a reagent in various organic transformations, including dehydration reactions and acylation processes.

Safety and Handling

N-Methylformamide is considered to be a hazardous chemical. It can cause irritation to the skin, eyes, and respiratory tract. Prolonged exposure may lead to more serious health effects, including liver and kidney damage. Proper safety precautions, such as the use of personal protective equipment and adequate ventilation, should be observed when handling this compound.

Related Compounds

Structure of Formothion, a related compound

N-Methylformamide is related to other formamide derivatives, such as dimethylformamide (DMF) and formamide itself. These compounds share similar chemical properties and are often used in similar applications.

Related Pages

• Formamide
• Dimethylformamide
• Methylamine
• Solvent