2-Nitrodiphenylamine

2-Nitrodiphenylamine
Identifiers
CAS number	119-75-5
ChemSpider	8100 Y
Jmol-3D images	Image 1 Image 2
SMILES O=[N+]([O-])C1=C(NC2=CC=CC=C2)C=CC=C1 [O-][N+](=O)c2ccccc2Nc1ccccc1
InChI InChI=1S/C12H10N2O2/c15-14(16)12-9-5-4-8-11(12)13-10-6-2-1-3-7-10/h1-9,13H Y Key: RUKISNQKOIKZGT-UHFFFAOYSA-N Y InChI=1/C12H10N2O2/c15-14(16)12-9-5-4-8-11(12)13-10-6-2-1-3-7-10/h1-9,13H Key: RUKISNQKOIKZGT-UHFFFAOYAD
Properties
Molecular formula	C12H10N2O2
Molar mass	214.22 g mol−1
Melting point	74 - 75 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

2-Nitrodiphenylamine, also called NDPA, 2-NDPA, 2NO2DPA, Sudan Yellow 1339, C.I. 10335, CI 10335, phenyl 2-nitrophenylamine, 2-nitro-N-phenylaniline, or N-phenyl-o-nitroaniline, is an organic chemical, a nitrated aromatic amine, a derivate of diphenylamine. Its chemical formula is C₁₂H₁₀N₂O₂, or C₆H₅NHC₆H₄NO₂. It is a red crystalline solid, usually in form of flakes or powder, with melting point of 74-76 °C and boiling point of 346 °C. It is polar but hydrophobic.

2-Nitrodiphenylamine is used as a stabilizer for synthetic rubbers, explosives, propellants (e.g. in Otto fuel II, smokeless powders, in some US Army double-base propellants in solid rockets, and in other applications involving nitric acid esters), plastics, and lubricants. It is also an intermediate for organic synthesis, and a civilian solvent dye.

In some explosives, it is used to control the explosion. One of its major uses is to control the explosion rate of propylene glycol dinitrate.

As a stabilizer, its major role is to eliminate the acidic nitrates and nitrogen oxides produced by gradual decomposition of nitric acid esters, which would otherwise autocatalyze further decomposition. Its amount is usually 1-2% of the mixture; higher amounts than 2% degrade the propellant's ballistic properties. The amount of the stabilizer depletes with time; remaining content of less than 0.5% (with initial 2% content) requires increased surveillance of the munition, with less than 0.2% warranting immediate disposal, as the depletion of the stabilizer may lead to autoignition of the propellant.^[1]

Other stabilizers of a similar nature are 4-nitrodiphenylamine, N-nitrosodiphenylamine, N-methyl-p-nitroaniline, and diphenylamine.

References

1. ^ http://chemicalland21.com/specialtychem/finechem/2-NITRODIPHENYLAMINE.htm

External links

• General information