My watch list
my.chemeurope.com  
Login  

Formamide



Formamide
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

Vapor pressure 0.08 mmHg at 20 °C
Acidity (pKa) 23.5 (in DMSO)[1]
Hazards
Flash point 154 °C (closed cup)
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.

Additional recommended knowledge

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.[2]

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

References

  1. ^ F. G. Bordwell, J. E. Bartmess and J. A. Hautala (1978). "Alkyl effects on equilibrium acidities of carbon acids in protic and dipolar aprotic media and the gas phase". J. Org. Chem. 43 (16): 3095-3101. doi:10.1021/jo00410a001.
  2. ^ Vimal K. Kamineni, Yuri M. Lvov, and Tabbetha A. Dobbins (2007). "Layer-by-Layer Nanoassembly of Polyelectrolytes Using Formamide as the Working Medium". Langmuir 23 (14): 7423-7427. doi:10.1021/la700465n.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Formamide". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE