HCONH2

HCONH2, commonly known as formamide, is the simplest amide of formic acid. Its chemical formula is C1H3NO, and its structure consists of a formyl group (H-CO-) attached to an amino group (−NH2). The SMILES representation is NC(=O)H. Formamide is a polar, hydrogen-bonding solvent and reagent used in a variety of chemical applications.

Formamide is a colorless, hygroscopic liquid at room temperature with a high boiling point of about 210 °C. It is miscible with water and many organic solvents and exhibits strong hydrogen-bonding interactions, contributing to its high polarity and solvent power. It is relatively stable under standard conditions but can hydrolyze to formic acid and ammonia in the presence of water and catalysts.

Industrial and laboratory preparation often involves dehydration of ammonium formate by heating, which yields formamide and water. It can also arise as a byproduct in other chemical processes. Due to its solvent properties, formamide is used in organic synthesis, polymer chemistry, and various assays; it serves as a reaction medium and as a precursor in the preparation of certain pharmaceuticals and nitrile syntheses. It is also employed in peptide synthesis and in laboratories as a denaturing solvent for nucleic acids.

Safety considerations are important when handling formamide. It is hazardous if inhaled, ingested, or absorbed through the skin and may cause irritation and reproductive toxicity in animal studies. It should be used with appropriate engineering controls, gloves, and eye protection, and it should be stored away from incompatible materials and strong oxidizers.