Formamide

Formamide
IUPAC name	Methanamide
Other names	Carbamaldehyde
Identifiers
CAS number	75-12-7 Y
SMILES	C(=O)N
Properties
Molecular formula	CH3NO
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)
Related compounds
Related compounds	Dimethylformamide
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox 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. 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]

Formamide will begin to partially decompose into carbon monoxide and ammonia at 180°C. When heated strongly, formamide decomposes to hydrogen cyanide (HCN) and water vapor.

Since formamide is a liquid when commonly used in the molecular biology/biochemistry lab, knowing its neat concentration is useful. This value is calculated by taking the density (1.133 g/cm³), multiplying by 1000 to convert into g/L and then dividing by the molecular weight (45.04 g/mol), giving a neat concentration of 25.16 M.

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:

HCOOH + NH₃ → HCOONH₄

HCOONH₄ → HCONH₂ + H₂O

Today's industrial method is based on aminolysis of methyl formate:

HCOOCH₃ + NH₃ → HCONH₂ + CH₃OH

Hypothetical Biochemistry

Formamide has also been put forward as an alternative solvent to water, perhaps with the ability to support life with alternative biochemistries to that found on Earth^[3].

Self-Replication

Formamide is self complimentary and so can cause dissolved carbon monoxide and ammonia to be reacted to form copies of itself. If heated slightly and in the presence of these chemicals, the formamide will slowly grow in quantity.

Health Information

Formamide is highly corrosive on contact with skin or eyes and may be deadly if ingested. Inhalation of large amounts of formamide vapor may require medical attention. ^[4] It is also a teratogen^[5]. Formamide should never be handled without proper safety attire including gloves and goggles.

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. 
3. ^ http://www.astrobio.net/news/article2171.html
4. ^ http://www.jtbaker.com/msds/englishhtml/f5770.htm
5. ^ http://www.bath.ac.uk/internal/bio-sci/bbsafe/formamide.htm