4-nitroaniline

4-Nitroaniline

Names
Preferred IUPAC name 4-Nitroaniline
Systematic IUPAC name 4-Nitrobenzenamine
Other names p-Nitroaniline 1-Amino-4-nitrobenzene p-Nitrophenylamine
Identifiers
CAS Number	100-01-6 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17064 N
ChemSpider	13846959 N
ECHA InfoCard	100.002.555
UNII	1MRQ0QZG7G Y
InChI InChI=1S/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H2 N Key: TYMLOMAKGOJONV-UHFFFAOYSA-N N InChI=1/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H2 Key: TYMLOMAKGOJONV-UHFFFAOYAW
SMILES c1cc(ccc1N)N(=O)=O
Properties
Chemical formula	C6H6N2O2
Molar mass	138.12 g/mol
Appearance	yellow or brown powder
Odor	faint, ammonia-like
Density	1.437 g/ml, solid
Melting point	146 to 149 °C (295 to 300 °F; 419 to 422 K) (lit.)
Boiling point	332 °C (630 °F; 605 K)
Solubility in water	0.8 mg/ml at 18.5 °C (IPCS)
Vapor pressure	0.00002 mmHg (20°C)
Magnetic susceptibility (χ)	-66.43·10−6 cm3/mol
Hazards
Main hazards	Toxic
Safety data sheet	JT Baker
EU classification (DSD)	T N
R-phrases	R23/24/25 R33 R52/53
S-phrases	S28 S36/37 S45 S61
NFPA 704	1 2 0
Flash point	199 °C (390 °F; 472 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	3249 mg/kg (rat, oral) 750 mg/kg (rat, oral) 450 mg/kg (guinea pig, oral) 810 mg/kg (mouse, oral)
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 6 mg/m3 (1 ppm) [skin]
REL (Recommended)	TWA 3 mg/m3 [skin]
IDLH (Immediate danger)	300 mg/m3
Related compounds
Related compounds	2-Nitroaniline, 3-Nitroaniline
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

4-Nitroaniline, p-nitroaniline or 1-amino-4-nitrobenzene is an organic compound with the formula C₆H₆N₂O₂. It is an organic chemical compound, consisting of a phenyl group attached to an amino group which is para to a nitro group. This chemical is commonly used as an intermediate in the synthesis of dyes, antioxidants, pharmaceuticals, and gasoline, in gum inhibitors, poultry medicines, and as a corrosion inhibitor.

It is produced industrially via the amination of 4-nitrochlorobenzene:

Below is a laboratory synthesis of 4-nitroaniline from aniline. The key step in this reaction sequence is an electrophilic aromatic substitution to install the nitro group para to the amino group. After this reaction, a separation must be performed to remove 2-nitroaniline, which is also formed in a small amount during the reaction.

4-Nitroaniline is mainly consumed industrially as a precursor to p-phenylenediamine, an important dye component. The reduction is effected using iron metal and by catalytic hydrogenation.

It is a starting material for the synthesis of Para Red, the first azo dye:

When heated, it polymerizes explosively into a rigid foam.

Nitroaniline is a used for determining Kamlet-Taft solvent parameters. The position of its UV-visual peak changes with the balance of hydrogen bonding acceptors and donors in the solvent.