Formamide
From Wikipedia, the free encyclopedia
| 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 |
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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. In capillary electrophoresis, it is used for stabilizing (single) strands of denatured DNA.
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]
[edit] Production
In the lab and in the past, formic acid was reacted with ammonia to produce ammonium formate, which can then be turned into formamide by heating:
Today's industrial method is based on aminolysis of methyl formate:
[edit] References
- ^ 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:.
- ^ 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:.
