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Topic summary

Aniline

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Names Preferred IUPAC name
Aniline
Systematic IUPAC name
Benzenamine
Other names
Phenylamine
Aminobenzene
Benzamine
Identifiers
3D model (JSmol)
Abbreviations PhNH2
H2NPh 605631 ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.000.491EC Number
  • 200-539-3
2796 KEGG
RTECS number
  • BW6650000
UNII
UN number1547
  • InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
    Key: PAYRUJLWNCNPSJ-UHFFFAOYSA-N
  • InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
    Key: PAYRUJLWNCNPSJ-UHFFFAOYAP
  • Nc1ccccc1
  • c1ccc(cc1)N
Properties C6H7NMolar mass93.129 g·mol Appearance Colorless liquid Density1.0297 g/mL Melting point−6.30 °C (20.66 °F; 266.85 K) Boiling point184.13 °C (363.43 °F; 457.28 K) Critical point (T, P) 698.8 K (425.7 °C), 4890 kPa 3.6 g/(100 mL) at 20 °C Vapor pressure0.6 mmHg (20 °C) Acidity (pKa)
  • 4.63 (conjugate acid; H2O)
−62.95·10 cm/mol 1.58364 Viscosity3.71 cP (3.71 mPa·s at 25 °C) Thermochemistry 193.7 J/(mol K) 191 J/(mol K) 31 kJ/mol –3393 kJ/mol 10.54 kJ/mol 55.83 kJ/mol at 25 °C Hazards Occupational safety and health (OHS/OSH):
Main hazards
potential occupational carcinogen GHS labelling: DangerH301, H311, H317, H318, H331, H341, H351, H372, H400P201, P202, P260, P264, P270, P271, P272, P273, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P311, P312, P314, P321, P322, P330, P333+P313, P361, P363, P391, P403+P233, P405, P501NFPA 704 (fire diamond)
3
2
0
Flash point70 °C (158 °F; 343 K) 770 °C (1,420 °F; 1,040 K) Explosive limits1.3–11% Lethal dose or concentration (LD, LC): 195 mg/kg (dog, oral)
250 mg/kg (rat, oral)
464 mg/kg (mouse, oral)
440 mg/kg (rat, oral)
400 mg/kg (guinea pig, oral) 175 ppm (mouse, 7 h) 250 ppm (rat, 4 h)
180 ppm (cat, 8 h) NIOSH (US health exposure limits):
PEL (Permissible)
TWA 5 ppm (19 mg/m) [skin]
REL (Recommended)
Ca [potential occupational carcinogen]
IDLH (Immediate danger)
100 ppm Related compounds 1-Naphthylamine
2-Naphthylamine
Related compounds
Phenylhydrazine
Nitrosobenzene
NitrobenzeneSupplementary data page Aniline (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Aniline (From Portuguese: anil, meaning 'indigo shrub', and -ine indicating a derived substance) is an organic compound with the formulaC6H5NH2. Consisting of a phenyl group (−C6H5) attached to an amino group (−NH2), aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans.

Relative to benzene, aniline is "electron-rich". It thus participates more rapidly in electrophilic aromatic substitution reactions. Likewise, it is also prone to oxidation: while freshly purified aniline is an almost colorless oil, exposure to air results in gradual darkening to yellow or red, due to the formation of strongly colored, oxidized impurities. Aniline can be diazotized to give a diazonium salt, which can then undergo various nucleophilic substitution reactions.

Like other amines, aniline is both a base (pKaH = 4.6) and a nucleophile, although less so than structurally similar aliphatic amines.

Because an early source of the benzene from which they are derived was coal tar, aniline dyes are also called coal tar dyes.

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