Nitramide

Organyl derivatives of nitramide, RNHNO₂ and R₂NNO₂ are termed nitroamines, and are widely used as explosives: examples include RDX and HMX. It is an isomer of hyponitrous acid.

Nitramide

Names
IUPAC name Nitramide
Other names Nitramine
Identifiers
CAS Number	7782-94-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:29273 Y
ChemSpider	22941 Y
PubChem CID	24534
UNII	B8N6F7BJTL Y
CompTox Dashboard (EPA)	DTXSID20999028
InChI InChI=1S/H2N2O2/c1-2(3)4/h1H2 Y Key: SFDJOSRHYKHMOK-UHFFFAOYSA-N Y InChI=1/H2N2O2/c1-2(3)4/h1H2 Key: SFDJOSRHYKHMOK-UHFFFAOYAT
SMILES N[N+](=O)[O-]
Properties
Chemical formula	H2N2O2
Molar mass	62.03 g mol−1
Appearance	Colorless solid
Density	1.378 g/cm3
Melting point	72 to 75 °C (162 to 167 °F; 345 to 348 K)
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

The nitramide molecule is essentially an amine group (−NH₂) bonded to a nitro group (−NO₂). It is reported to be non-planar in the gas phase, but planar in the crystal phase.

Thiele and Lachman's original synthesis of nitramide involved the hydrolysis of potassium nitrocarbamate:

${\displaystyle {\ce {K2(O2NNCO2) + 2H2SO4 -> O2NNH2 + CO2 + 2KHSO4}}}$ 

Other routes to nitramide include hydrolysis of nitrocarbamic acid,

${\displaystyle {\ce {O2NNHCO2H -> O2NNH2 + CO2}}}$ 

reaction of sodium sulfamate with nitric acid,

${\displaystyle {\ce {Na(SO3NH2) + HNO3 -> O2NNH2 + NaHSO4}}}$ 

and reaction of dinitrogen pentoxide with two equivalents of ammonia.

${\displaystyle {\ce {N2O5 + 2NH3 -> O2NNH2 + NH4NO3}}}$ 

Also called nitramines, organic nitramides are important explosives. They are prepared by nitrolysis of hexamethylenetetramine.