Formamide

Formamide

Names
Preferred IUPAC name Formamide
Systematic IUPAC name Methanamide
Other names Carbamaldehyde
Identifiers
CAS Number	75-12-7 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:48431 Y
ChEMBL	ChEMBL266160 Y
ChemSpider	693 Y
ECHA InfoCard	100.000.766
IUPHAR/BPS	4739
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)
Magnetic susceptibility (χ)	-21.9·10−6 cm3/mol
Hazards
NFPA 704	1 2 0
Flash point	154 °C (309 °F; 427 K) (closed cup)
US health exposure limits (NIOSH):
PEL (Permissible)	none
REL (Recommended)	TWA 10 ppm (15 mg/m3) [skin]
IDLH (Immediate danger)	N.D.
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  (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:

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

Formamide is also generated by aminolysis of ethyl formate:

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

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

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