Nitrobenzene

Nitrobenzene

Names
Preferred IUPAC name Nitrobenzene
Other names Nitrobenzol Oil of mirbane
Identifiers
CAS Number	98-95-3 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:27798 Y
ChEMBL	ChEMBL15750 Y
ChemSpider	7138 Y
ECHA InfoCard	100.002.469
KEGG	C06813 Y
PubChem	7416
RTECS number	DA6475000
UNII	E57JCN6SSY N
InChI InChI=1S/C6H5NO2/c8-7(9)6-4-2-1-3-5-6/h1-5H Y Key: LQNUZADURLCDLV-UHFFFAOYSA-N Y InChI=1/C6H5NO2/c8-7(9)6-4-2-1-3-5-6/h1-5H Key: LQNUZADURLCDLV-UHFFFAOYAA
SMILES c1ccc(cc1)[N+](=O)[O-]
Properties
Chemical formula	C6H5NO2
Molar mass	123.06 g/mol
Appearance	yellowish, oily liquid
Odor	pungent, like paste shoe polish
Density	1.199 g/cm3
Melting point	5.7 °C (42.3 °F; 278.8 K)
Boiling point	210.9 °C (411.6 °F; 484.0 K)
Solubility in water	0.19 g/100 ml at 20 °C
Vapor pressure	0.3 mmHg (25°C)
Magnetic susceptibility (χ)	-61.80·10−6 cm3/mol
Hazards
EU classification (DSD)	T F N
R-phrases	R10, R23/24/25, R40, R48/23/24, R51/53, R62
S-phrases	(S1/2), S28, S36/37, S45, S61
NFPA 704	2 3 1
Flash point	88 °C (190 °F; 361 K)
Autoignition temperature	480 °C (896 °F; 753 K)
Explosive limits	1.8%-?
Lethal dose or concentration (LD, LC):
LD50 (median dose)	780 mg/kg (rat, oral) 600 mg/kg (rat, oral) 590 mg/kg (mouse, oral)
LDLo (lowest published)	750 mg/kg (dog, oral)
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 1 ppm (5 mg/m3) [skin]
REL (Recommended)	TWA 1 ppm (5 mg/m3) [skin]
IDLH (Immediate danger)	200 ppm
Related compounds
Related compounds	Aniline Benzenediazonium chloride Nitrosobenzene
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

Nitrobenzene is an organic compound with the chemical formula C₆H₅NO₂. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor to aniline. In the laboratory, it is occasionally used as a solvent, especially for electrophilic reagents.

Nitrobenzene is prepared by nitration of benzene with a mixture of concentrated sulfuric acid, water, and nitric acid. This mixture is sometimes called "mixed acid." The production of nitrobenzene is one of the most dangerous processes conducted in the chemical industry because of the exothermicity of the reaction (ΔH = −117 kJ/mol).

World capacity for nitrobenzene in 1985 was about 1.7×10⁶tonnes.

The nitration process involves formation of the nitronium ion (NO₂⁺), followed by an electrophilic aromatic substitution reaction of it with benzene. The nitronium ion is generated in situ by the reaction of nitric acid and an acidic dehydration agent, typically sulfuric acid:

Approximately 97% of nitrobenzene is consumed in the production of aniline, which is a precursor to rubber chemicals, pesticides, dyes (particularly azo dyes), explosives, and pharmaceuticals.