Formamide

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Formamide
Names
IUPAC name
Formamide
Preferred IUPAC name
Formamide
Systematic IUPAC name
Methanamide
Other names
Carbamaldehyde
Properties
CH3NO
Molar mass 45.04 g/mol
Appearance Colorless liquid
Odor Ammonia-like
Density 1.133 g/cm3 (20 °C)
Melting point 2.55 °C (36.59 °F; 275.70 K)
Boiling point 210 °C (410 °F; 483 K)
Miscible
Solubility Miscible with acetic acid, acetone, chloroform, dichloromethane, diethyl ether, dioxane, ethanol, ethylene glycol, glycerol, isopropanol, methanol, petroleum ether, phenol
Vapor pressure 0.08 mmHg (20 °C)
Acidity (pKa) 23.5 (in DMSO)
Hazards
Safety data sheet Sigma-Aldrich
Flash point 154 °C (309 °F; 427 K)
Lethal dose or concentration (LD, LC):
5.325 mg/kg (rat, oral)
Related compounds
Related compounds
Dimethylformamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Formamide, also known as methanamide, is an amide derived from formic acid, a clear liquid with an ammonia-like odor.

Properties

Chemical

Thermal decomposition of formamide at 180 °C yields carbon monoxide and ammonia, as well as traces of hydrogen cyanide.

HC(O)NH2 → CO + NH3

If the decomposition occurs in the presence of solid acid catalysts, formamide dehydrates to HCN:[1]

HC(O)NH2 → HCN + H2O

Physical

Formamide is colorless liquid with an ammonia-like odor miscible in water and many organic compounds.

Availability

Formamide is sold by chemical suppliers.

Preparation

Formamide can be prepared from the pyrolysis of ammonium acetate, which in turn is made by neutralizing ammonia with formic acid.

HCOOH + NH3 → HCOONH4
HCOONH4 → HCONH2 + H2O

Formamide can also be obtained from the aminolysis of ethyl formate:

HCOOCH2CH3 + NH3 → HCONH2 + CH3CH2OH

Projects

Handling

Safety

Formamide is moderately irritating to the skin, eyes and mucous membranes. Formamide has been shown to exhibit hematoxicity in animals and prolonged exposure via inhalation or dermal absorption is considered hazardous. It is also classified as teratogen. Formamide should never be handled without proper safety attire including gloves and goggles.

Storage

In closed bottles.

Disposal

Should be mixed with a more flammable solvent and incinerated.

References

  1. https://onlinelibrary.wiley.com/doi/10.1002/14356007.a12_001.pub2/otherversions

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