Nitrobenzene

Nitrobenzene

Other names[hide]
Nitrobenzol
Oil of mirbane
Identifiers
CAS number

98-95-3

PubChem

7416

ChemSpider

7138

UNII

E57JCN6SSY

KEGG

C06813

ChEBI

CHEBI:27798

ChEMBL

CHEMBL15750

RTECS number

DA6475000

Jmol-3D images

Image 1
SMILES

[show]

InChI
[show]

Properties
Molecular formula

C6H5NO2

Molar mass

123.06 g/mol

Appearance

yellowish liquid

Density

1.199 g/cm3

Melting point

Boiling point

Solubility in water

5.7 C

210.9 C
0.19 g/100 ml at 20 C
Hazards

EU classification

Toxic (T)
Carc. Cat. 3
Repr. Cat. 3
Dangerous for the environment (N)
Flammable(F)

R-phrases

R10, R23/24/25, R40,

R48/23/24, R51/53, R62

S-phrases

(S1/2), S28, S36/37,

S45, S61

NFPA 704

3
2
1
Flash point

88 C

Autoignition

525 C

temperature
Related compounds
Related compounds

Aniline
Benzenediazonium chloride
Nitrosobenzene
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Except where noted otherwise, data are given for materials in their standard
state (at 25 C, 100 kPa)
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.
Contents
[hide]

1 Production
1.1 Mechanism of nitration

o
2 Uses
o

2.1 Specialized applications

2.2 Organic reactions

3 Safety
4 References

5 External links

Production [edit]
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 (H =
117 kJ/mol).[1]

World capacity for nitrobenzene in 1985 was about 1.7106 tonnes.[1]

Mechanism of nitration [edit]

Main article: nitration
The reaction pathway entails formation of an adduct between the Lewis acidic nitroniumion (NO2+) and
benzene. The nitronium ion is generated in situ by the reaction of nitric acid and an acidic dehydration
agent, typically sulfuric acid:
HNO3 + H+

NO2+ + H2O

Uses [edit]
Approximately 95% of nitrobenzene is consumed in the production of aniline,[1] which is a precursor
to rubber chemicals, pesticides, dyes, explosives, and pharmaceuticals.

Specialized applications [edit]

Nitrobenzene is also used in shoe and floor polishes, leather dressings, paint solvents, and other
materials to mask unpleasant odors. Redistilled, as oil of mirbane, nitrobenzene has been used as an
inexpensive perfume for soaps. A significant merchant market for nitrobenzene is its use in the
production of the analgesic paracetamol (also known as acetaminophen) (Mannsville 1991).
[2]

Nitrobenzene is also used in Kerr cells, as it has an unusually large Kerr constant.

Organic reactions [edit]

Aside from its conversion to aniline, nitrobenzene is readily converted to related derivatives such
as azobenzene,[3] nitrosobenzene,[4] and phenylhydroxylamine.[5] The nitro- group is deactivating, thus
substitution tends to occur at the meta-position.

Safety [edit]

Nitrobenzene is highly toxic (Threshold Limit Value 5 mg/m3) and readily absorbed through the skin.
Prolonged exposure may cause serious damage to the central nervous system, impair vision, cause
liver or kidney damage, anemia and lung irritation. Inhalation of vapors may induce headache,
nausea, fatigue, dizziness, cyanosis, weakness in the arms and legs, and in rare cases may be fatal.
The oil is readily absorbed through the skin and may increase heart rate, cause convulsions or rarely
death. Ingestion may similarly cause headaches, dizziness, nausea, vomiting and gastrointestinal
irritation, loss of sensation/use in limbs and also causes internal bleeding. [6]
Nitrobenzene is considered a likely human carcinogen by the United States Environmental Protection
Agency,[7] and is classified by the IARC as a Group 2B carcinogen which is "possibly carcinogenic to
humans".[8] It has been shown to cause liver, kidney, and thyroid adenomas and carcinomas in rats. [9]