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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17064 ;
ChEMBL	ChEMBL14282 ;
ChemSpider	13846959 ;
ECHA InfoCard	100.002.555
UNII	1MRQ0QZG7G ;
CompTox Dashboard (EPA)	DTXSID8020961 ;
	InChI InChI=1S/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H2 Key: TYMLOMAKGOJONV-UHFFFAOYSA-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
	Occupational safety and health (OHS/OSH):
Main hazards	Toxic
NFPA 704 (fire diamond)	2 1 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)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 6 mg/m3 (1 ppm) [skin]
REL (Recommended)	TWA 3 mg/m3 [skin]
IDLH (Immediate danger)	300 mg/m3
Safety data sheet (SDS)	JT Baker
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). verify (what is ?) 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 benzene ring in which an amino group 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.

Synthesis

It is produced industrially via the amination of 4-nitrochlorobenzene:^[3]

ClC₆H₄NO₂ + 2 NH₃ → H₂NC₆H₄NO₂ + NH₄Cl

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]

Applications

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.^[3]

It is a starting material for the synthesis of Para Red, the first azo dye:^[5]

When heated with sulfuric acid, it polymerizes explosively into a rigid foam.^[6]

Laboratory use

Nitroaniline is a solvatochromic dye 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.^{[citation needed]}

Toxicity

The compound is toxic by way of inhalation, ingestion, and absorption, and should be handled with care. Its LD₅₀ in rats is 750 mg/kg when administered orally. 4-Nitroaniline is particularly harmful to all aquatic organisms, and can cause long-term damage to the environment if released as a pollutant.^{[citation needed]}

References

^ ^a ^b ^c ^d NIOSH Pocket Guide to Chemical Hazards. "#0449". National Institute for Occupational Safety and Health (NIOSH).
^ "p-Nitroaniline". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b Gerald Booth (2007). "Nitro Compounds, Aromatic". Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. {{cite journal}}: Cite journal requires |journal= (help); Unknown parameter |encyclopedia= ignored (help)
^ Mohrig, J.R.; Morrill, T.C.; Hammond, C.N.; Neckers, D.C. "Synthesis 5: Synthesis of the Dye Para Red from Aniline." Experimental Organic Chemistry. Freeman: New York, NY, 1997; pp 456-467.
^ Williamson, Kenneth L. (2002). Macroscale and Microscale Organic Experiments, Fourth Edition. Houghton-Mifflin. ISBN 0-618-19702-8.
^ "Studies on nitroaniline–sulfuric acid compositions: Aphrogenic pyrostats". doi:10.1002/app.1970.070140813. {{cite journal}}: Cite journal requires |journal= (help)

External links

[PGCH-1] NIOSH Pocket Guide to Chemical Hazards. "#0449". National Institute for Occupational Safety and Health (NIOSH).

[2] "p-Nitroaniline". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[Ullmann-3] Gerald Booth (2007). "Nitro Compounds, Aromatic". Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. {{cite journal}}: Cite journal requires |journal= (help); Unknown parameter |encyclopedia= ignored (help)

[4] Mohrig, J.R.; Morrill, T.C.; Hammond, C.N.; Neckers, D.C. "Synthesis 5: Synthesis of the Dye Para Red from Aniline." Experimental Organic Chemistry. Freeman: New York, NY, 1997; pp 456-467.

[5] Williamson, Kenneth L. (2002). Macroscale and Microscale Organic Experiments, Fourth Edition. Houghton-Mifflin. ISBN 0-618-19702-8.

[6] "Studies on nitroaniline–sulfuric acid compositions: Aphrogenic pyrostats". doi:10.1002/app.1970.070140813. {{cite journal}}: Cite journal requires |journal= (help)

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