Formamide

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Formamide
Image:Formamide-2D.png
Image:Formamide-3D-vdW.png
IUPAC name	Methanamide
Other names	Carbamaldehyde
Identifiers
CAS number	75-12-7
SMILES	C(=O)N
Properties
Molecular formula	HCONH2
Molar mass	45.04 g/mol
Density	1.133 g/cm³
Melting point	2-3 °C
Boiling point	210 °C
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

Contents 1 Production 2 Physical data 3 References 4 External links

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/la700465nde:Formamid