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nitrobenzene
Sign in to saveAlso known as essence of mirbane, nitrobenzol, oil of mirbane
Nitrobenzene is an aromatic nitro compound and the simplest of the nitrobenzenes, 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. As confirmed by X-ray crystallography, nitrobenzene is a planar molecule.
Chemical data
- Formula
- C6H5NO2
- Molecular weight
- 123.11 g/mol
- IUPAC name
- nitrobenzene
- SMILES
- C1=CC=C(C=C1)[N+](=O)[O-]
- InChIKey
- LQNUZADURLCDLV-UHFFFAOYSA-N
- XLogP
- 1.9
- Polar surface area
- 45.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 123.032
Show 17 more facts
- MCN code
- 2904.20.51
- melting point
- 5.7
- Commons category
- Nitrobenzene
- chemical formula
- C₆H₅NO₂
- NIOSH Pocket Guide ID
- 0450
- density
- 1.20
- speed of sound
- 1463
- immediately dangerous to life or health
- 1008
- boiling point
- 210.8
- vapor pressure
- 0.3
- flash point
- 190
- solubility
- 0.2
- lower flammable limit
- 1.8
- ionization energy
- 9.86
- time-weighted average exposure limit
- 5
- canonical SMILES
- C1=CC=C(C=C1)[N+](=O)[O-]
- electric dipole moment
- 4.22
Sources (7)
via Wikidata · CC0
~4 min read
Article
7 sectionsContents
- Production
- Uses
- Specialized applications
- Organic reactions
- Safety
- References
- External links
Nitrobenzene is an aromatic nitro compound and the simplest of the nitrobenzenes, 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. As confirmed by X-ray crystallography, nitrobenzene is a planar molecule.
==Production== 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." class=skin-invert-image|center|frameless|333x333px 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).