Oxamide

Oxamide is the organic compound with the formula (CONH₂)₂. This white crystalline solid is soluble in ethanol, slightly soluble in water and insoluble in diethyl ether. Oxamide is the diamide derived from oxalic acid, and the hydrate of cyanogen.

Oxamide

Names
Preferred IUPAC name Oxamide
Systematic IUPAC name Ethanediamide
Other names Oxalamide Oxamimidic acid Diaminoglyoxal Oxalic acid diamide 1-Carbamoyl-formimidic acid
Identifiers
CAS Number	471-46-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:48248^N
ChemSpider	9709^N
ECHA InfoCard	100.006.767
EC Number	207-442-5
PubChem CID	10113
UNII	SBE4M0223E^Y
CompTox Dashboard (EPA)	DTXSID1060051
InChI InChI=1S/C2H4N2O2/c3-1(5)2(4)6/h(H2,3,5)(H2,4,6)^N Key: YIKSCQDJHCMVMK-UHFFFAOYSA-N^N InChI=1/C2H4N2O2/c3-1(5)2(4)6/h(H2,3,5)(H2,4,6) Key: YIKSCQDJHCMVMK-UHFFFAOYAL
SMILES NC(=O)C(N)=O
Properties
Chemical formula	(CONH2)2
Molar mass	88.0654 g/mol
Appearance	White powder
Density	1.667 g/cm^3
Melting point	122 °C (252 °F; 395 K)
Boiling point	324 °C (615 °F; 597 K) , decomposes above 350 °C
Solubility in water	Slightly soluble
Solubility	Soluble in ethanol, insoluble in diethyl ether
Magnetic susceptibility (χ)	−39.0·10^−6 cm^3/mol
Hazards
Flash point	> 300 °C (572 °F; 573 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Preparation

Oxamide is produced from hydrogen cyanide, which is oxidized to cyanogen, which is then hydrolyzed.

It can also be prepared from formamide by glow-discharge electrolysis.

Application

The main application is as a substitute for urea in fertilizers. Oxamide hydrolyzes (releases ammonia) very slowly, which is sometimes preferred vs the quick release by urea.

It is used as a stabilizer for nitrocellulose preparations. It also finds use in APCP rocket motors as a high performance burn rate suppressant. The use of oxamide in concentrations of 1-3 wt% has shown to slow the linear burn rate while having minimal impact on propellant specific impulse.

N,N'-substituted oxamides are supporting ligands for the copper-catalyzed amination and amidation of aryl halides in Ullmann-Goldberg reaction, including relatively unreactive aryl chloride substrates.

Reactions

It dehydrates above 350 °C releasing cyanogen. Oxamide derivatives form self-assembled monolayers consisting of a hydrogen bonded network.