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4-nitroaniline

4-Nitroaniline
Skeletal formula of p-nitroaniline
Ball-and-stick model of the p-nitroaniline molecule
Names
Preferred IUPAC name
4-Nitroaniline
Systematic IUPAC name
4-Nitrobenzenamine
Other names
p-Nitroaniline
1-Amino-4-nitrobenzene
p-Nitrophenylamine
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.555
UNII
Properties
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)
0.8 mg/ml at 18.5 °C (IPCS)
Vapor pressure 0.00002 mmHg (20°C)
-66.43·10−6 cm3/mol
Hazards
Main hazards Toxic
Safety data sheet JT Baker
Toxic T Dangerous for the Environment (Nature) N
R-phrases R23/24/25 R33 R52/53
S-phrases S28 S36/37 S45 S61
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
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 YesYN ?)
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.
Synthesis of nitroaniline.svg

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.


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