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
CAS Number	119-75-5 N
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL1450018
ChemSpider	8100 Y
ECHA InfoCard	100.003.953
EC Number	204-348-6
PubChem CID	8407
UNII	DT9NA7ZDD8 Y
UN number	1661
CompTox Dashboard (EPA)	DTXSID4025749
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
SMILES O=[N+]([O-])C1=C(NC2=CC=CC=C2)C=CC=C1 [O-][N+](=O)c2ccccc2Nc1ccccc1
Properties
Chemical formula	C12H10N2O2
Molar mass	214.224 g·mol−1
Melting point	74 to 75 °C (165 to 167 °F; 347 to 348 K)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, 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]