Aniline

Aniline

Names
Preferred IUPAC name Aniline
Systematic IUPAC name Benzenamine
Other names Phenylamine Aminobenzene Benzamine
Identifiers
CAS Number	62-53-3 Y 142-04-1 (HCl) N
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:17296 Y
ChEMBL	ChEMBL538 Y
ChemSpider	5889 Y
DrugBank	DB06728 Y
ECHA InfoCard	100.000.491
KEGG	C00292 Y
PubChem	6115 8870 (HCl)
UNII	SIR7XX2F1K Y
InChI InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2 Y Key: PAYRUJLWNCNPSJ-UHFFFAOYSA-N Y InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2 Key: PAYRUJLWNCNPSJ-UHFFFAOYAP
SMILES Nc1ccccc1 c1ccc(cc1)N
Properties
Chemical formula	C6H7N
Molar mass	93.13 g·mol−1
Appearance	Colorless to yellow liquid
Density	1.0217 g/mL
Melting point	−6.3 °C (20.7 °F; 266.8 K)
Boiling point	184.13 °C (363.43 °F; 457.28 K)
Solubility in water	3.6 g/100 mL at 20 °C
Vapor pressure	0.6 mmHg (20° C)
Basicity (pKb)	9.13
Magnetic susceptibility (χ)	-62.95·10−6 cm3/mol
Viscosity	3.71 cP (3.71 mPa·s at 25 °C
Thermochemistry
Std enthalpy of combustion (ΔcHo298)	-3394 kJ/mol
Hazards
Main hazards	potential occupational carcinogen
Safety data sheet	See: data page
EU classification (DSD)	T N
R-phrases	R23/24/25 R40 R41 R43 R48/23/24/25 R68 R50
S-phrases	(S1/2) S26 S27 S36/37/39 S45 S46 S61 S63
NFPA 704	2 3 0
Flash point	70 °C (158 °F; 343 K)
Autoignition temperature	770 °C (1,420 °F; 1,040 K)
Explosive limits	1.3%-11%
Lethal dose or concentration (LD, LC):
LDLo (lowest published)	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)
LC50 (median concentration)	175 ppm (mouse, 7 hr)
LCLo (lowest published)	250 ppm (rat, 4 hr) 180 ppm (cat, 8 hr)
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 5 ppm (19 mg/m3) [skin]
REL (Recommended)	Ca [potential occupational carcinogen]
IDLH (Immediate danger)	100 ppm
Related compounds
Related aromatic amines	1-Naphthylamine 2-Naphthylamine
Related compounds	Phenylhydrazine Nitrosobenzene Nitrobenzene
Supplementary data page
Structure and properties	Refractive index (n), Dielectric constant (εr), etc.
Thermodynamic data	Phase behaviour solid–liquid–gas
Spectral data	UV, IR, NMR, MS
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

Aniline is an organic compound with the formula C₆H₅NH₂. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Its main use is in the manufacture of precursors to polyurethane and other industrial chemicals. Like most volatile amines, it possesses the odour of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds.

Aniline is a planar molecule. The amine is nearly planar owing to conjugation of the lone pair with the aryl substituent. The C-N distance is correspondingly shorter. In aniline, the C-N and C-C distances are close to 1.39 Å, indicating the π-bonding between N and C.

Industrial aniline production involves two steps. First, benzene is nitrated with a concentrated mixture of nitric acid and sulfuric acid at 50 to 60 °C to yield nitrobenzene. The nitrobenzene is then hydrogenated (typically at 200–300 °C) in the presence of metal catalysts.

The reduction of nitrobenzene to aniline was first performed by Nikolay Zinin in 1842 using inorganic sulfide as a reductant (Zinin reaction).

Aniline can alternatively be prepared from ammonia and phenol derived from the cumene process.

In commerce, three brands of aniline are distinguished: aniline oil for blue, which is pure aniline; aniline oil for red, a mixture of equimolecular quantities of aniline and ortho- and para-toluidines; and aniline oil for safranine, which contains aniline and ortho-toluidine, and is obtained from the distillate (échappés) of the fuchsine fusion.