Formamide

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Template:Chembox E number
Formamide
IUPAC name Methanamide
Other names Carbamaldehyde
Identifiers
3D model (JSmol)
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Properties
HCONH2
Molar mass 45.04 g/mol
Density 1.133 g/cm³
Melting point
Boiling point
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Formamide, also known as methanamide, is an amide derived from formic acid. It is a clear liquid which is miscible with water and has an ammonia-like odor. It is used primarily for manufacturing sulfa drugs and synthesizing vitamins and as a softener for paper and fiber. In its pure form, it dissolves many ionic compounds that are insoluble in water, so it is also used as a solvent.

Formamide is also a constituent of cryoprotectant vitrification mixtures used for cryopreservation of tissues and organs.

Formamide is also used as an RNA stabiliser in gel electrophoresis by deionizing RNA.

Another use is to add it in sol-gel solutions in order to avoid cracking during sintering.

Formamide, in its pure state, has been used as an alternative solvent for the electrostatic self-assembly of polymer nanofilms.1

Production

The reaction of formic acid with ammonia produces ammonium formate, which can then be turned into formamide by heating:

HCOOH + NH3 → HCOONH4
HCOONH4 → HCONH2 + H2O

Physical data

Vapour density: 1.55 (air = 1)
Vapour pressure: 0.08 mm Hg (11 Pa) at 20 °C
Flash point: 154 °C (open cup)
pKa (DMSO): 23.5 (J. Org. Chem. 1978, 43, 3095)

References


External links

Vimal K. Kamineni, Yuri M. Lvov, and Tabbetha A. Dobbins "Layer-by-Layer Nanoassembly of Polyelectrolytes Using Formamide as the Working Medium" doi:10.1021/la700465n


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