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Aniline dye

Aniline
Aniline
Aniline
Space-filling model of solid aniline
Names
Preferred IUPAC name
Aniline
Systematic IUPAC name
Benzenamine
Other names
Phenylamine
Aminobenzene
Benzamine
Identifiers
62-53-3 YesY
142-04-1 (HCl) N
3D model (Jmol) Interactive image
Interactive image
ChEBI CHEBI:17296 YesY
ChEMBL ChEMBL538 YesY
ChemSpider 5889 YesY
DrugBank DB06728 YesY
ECHA InfoCard 100.000.491
KEGG C00292 YesY
PubChem 6115
8870 (HCl)
UNII SIR7XX2F1K YesY
Properties
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)
3.6 g/100 mL at 20 °C
Vapor pressure 0.6 mmHg (20° C)
Basicity (pKb) 9.13
-62.95·10−6 cm3/mol
Viscosity 3.71 cP (3.71 mPa·s at 25 °C
Thermochemistry
-3394 kJ/mol
Hazards
Main hazards potential occupational carcinogen
Safety data sheet See: data page
Toxic T Dangerous for the Environment (Nature) 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
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 70 °C (158 °F; 343 K)
770 °C (1,420 °F; 1,040 K)
Explosive limits 1.3%-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 hr)
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
1-Naphthylamine
2-Naphthylamine
Related compounds
Phenylhydrazine
Nitrosobenzene
Nitrobenzene
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
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 YesYN ?)
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.


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