Formamide

Formamide

Names
IUPAC name Methanamide
Other names Carbamaldehyde Formamide
Identifiers
CAS Number	75-12-7 Y
ChEBI	CHEBI:48431 Y
ChEMBL	ChEMBL266160 Y
ChemSpider	693 Y
IUPHAR/BPS	4739
Jmol 3D model	Interactive image
KEGG	C00488 Y
PubChem	713
InChI InChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3) Y Key: ZHNUHDYFZUAESO-UHFFFAOYSA-N Y InChI=1/CH3NO/c2-1-3/h1H,(H2,2,3) Key: ZHNUHDYFZUAESO-UHFFFAOYAQ
SMILES O=CN
Properties
Chemical formula	CH3NO
Molar mass	45.04 g/mol
Appearance	Colorless, oily liquid
Density	1.133 g/cm3
Melting point	2 to 3 °C (36 to 37 °F; 275 to 276 K)
Boiling point	210 °C (410 °F; 483 K)
Solubility in water	Miscible
Vapor pressure	0.08 mmHg at 20 °C
Acidity (pKa)	23.5 (in DMSO)
Vapor pressure	{{{value}}}
Related compounds
Related compounds	Carbamic acid Dimethylformamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
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 chemical feedstock for the manufacture of sulfa drugs, other pharmaceuticals, herbicides, pesticides and the manufacture of hydrocyanic acid. It has been used as a softener for paper and fiber. It is a solvent for many ionic compounds. It has also been used as a solvent for resins and plasticizers.

Formamide will begin to partially decompose into carbon monoxide and ammonia at 180 °C together with traces of hydrogen cyanide (HCN) and water. In the presence of solid acid catalysts, formamide yields HCN in high yield:

low temperature: HC(O)NH₂ → CO + NH₃

high temperature, acid-catalyzed: HC(O)NH₂ → HCN + H₂O

Production

Historical production

In the past, formamide was produced by treating formic acid with ammonia, which produces ammonium formate, which in turn yield formamide upon heating:

HCOOH + NH₃ → HCOONH₄

HCOONH₄ → HCONH₂ + H₂O

Formamide is also generated by aminolysis of ethyl formate:

HCOOCH₂CH₃ + NH₃ → HCONH₂ + CH₃CH₂OH

Modern production

The current industrial process for the manufacture of formamide involves either the carbonylation of ammonia:

CO + NH₃ → HCONH₂

An alternative two-stage process involves the aminolysis of methyl formate, which is formed from carbon monoxide and methanol:

CO + CH₃OH → HCOOCH₃

HCO₂CH₃ + NH₃ → HC(O)NH₂ + CH₃OH

Applications

Formamide is used in the industrial production of hydrogen cyanide. It is also used as a solvent for processing various polymers such as polyacrylonitrile.

Niche or laboratory applications

Formamide is 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.

Formamide is used to prepare primary amines directly from ketones via their N-formyl derivatives, using the Leuckart reaction.

Hypothetical biochemistry

Main article: Hypothetical types of biochemistry

Formamide has also been proposed as an alternative solvent to water, perhaps with the ability to support life with alternative biochemistries to that currently found on Earth. It can be formed by the reaction of hydrogen cyanide and water, has a large dipole moment, and dissolves almost everything that will dissolve in water.

RNA base creation

Formamide has been shown to create guanine at 130 °C in the presence of ultra violet light.

Safety

Formamide is moderately irritating to the eyes, skin and mucous membranes. Inhalation of large amounts of formamide vapor may require medical attention. It is also a teratogen. Formamide has been shown to exhibit hematoxicity in animals and is considered hazardous by prolonged exposure through inhalation, oral intake and dermal absorption. Formamide should never be handled without proper safety attire including gloves and goggles.