2-Nitrodiphenylamine

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
Names
Preferred IUPAC name
2-Nitro-N-phenylaniline
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.953
EC Number
  • 204-348-6
UN number 1661
Properties
C12H10N2O2
Molar mass 214.224 g·mol−1
Melting point 74 to 75 °C (165 to 167 °F; 347 to 348 K)
Hazards
GHS pictograms
GHS Signal word Warning
H315, H319, H335
P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
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

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. While N-methyl-p-nitroaniline(MNA also used in IMX-101), and diphenylamine(DPA) are more commonly employed.[2]

References
  1. "2-Nitrodiphenylamine (O-Nitro-N-Phenylaniline)".
  2. "PROPELLANT STABILIZERS". Archived from the original on 2014-07-15. Retrieved 2014-06-07.
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