What Is Formamide?
Formamide is an amide derived from formic acid with the chemical formula HCONH2. It is also known as methanamide and carbamaldehyde.
The 50% lethal dose (LD50) of formamide is a few grams per kilogram, indicating low acute toxicity and low mutagenicity.
Uses of Formamide
Formamide is used as an anti-freezing agent, and in cryopreservation of biological samples, such as mouse sperm. It acts as a “vitrification compound” that solidifies and supercools the object.
Additionally, formamide is utilized in the industrial production of hydrogen cyanide (HCN), a highly toxic substance used as an insecticide and rat poison.
Formamide is also employed in RNA stabilization in gel electrophoresis, stabilization of denatured DNA strands in capillary electrophoresis, synthesis of vitamins, production of sulfa drugs, and as a paper and fiber softener.
Properties of Formamide
Formamide is a colorless liquid with an ammoniacal odor. It has a melting point of 2-3 °C and a boiling point of 210 °C. It is miscible with alcohol and ether but insoluble in benzene and chloroform.
As a solvent, formamide can mix with water in any proportion and dissolve ionic compounds insoluble in water, including alkali metal salts of acetic acid and chlorides of lead, copper, and iron, as well as polymer compounds like glucose, casein, starch, and tannin.
Structure of Formamide
Formamide, with the differential formula HCONH2, is an amide of formic acid. It has a molecular weight of 45.04 g/mol and a density of 1.133 g/cm3.
Formamide is hypothesized as an alternative solvent to water in biochemistry due to its ability to sustain life and its production through the hydrolysis of hydrogen cyanide. Its large dipole moment gives it solvation properties similar to water.
Other Information on Formamide
1. Synthesis of Formamide
Formamide can be synthesized industrially by treating formic acid with ammonia to produce ammonium formate, which is then dehydrated. It can also be produced by aminolysis of methyl or ethyl formate with ammonia, or by carbonylation of ammonia.
Another method involves ammonolysis of methyl formate produced from carbon monoxide and methanol.
2. Reaction of Formamide
At 180 °C, formamide decomposes into carbon monoxide and ammonia. In the presence of a solid acid catalyst, it decomposes into hydrogen cyanide and water.
When heated under ultraviolet light, formamide can convert to trace amounts of guanine.