Aniline

Aniline
Names
	Preferred IUPAC name Aniline
	Systematic IUPAC name Benzenamine
	Other names Phenylamine; Aminobenzene; Benzamine
Identifiers
CAS Number	62-53-3 ; 142-04-1 (HCl) ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	605631
ChEBI	CHEBI:17296 ;
ChEMBL	ChEMBL538 ;
ChemSpider	5889 ;
DrugBank	DB06728 ;
ECHA InfoCard	100.000.491
EC Number	200-539-3;
Gmelin Reference	2796
KEGG	C00292 ;
PubChem CID	6115; 8870 (HCl);
RTECS number	BW6650000;
UNII	SIR7XX2F1K ; 576R1193YL (HCl) ;
UN number	1547
CompTox Dashboard (EPA)	DTXSID8020090 ;
	InChI 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;
	SMILES Nc1ccccc1; c1ccc(cc1)N;
Properties
Chemical formula	C6H5NH2
Molar mass	93.129 g·mol−1
Appearance	Colorless liquid
Density	1.0297 g/mL
Melting point	−6.30 °C (20.66 °F; 266.85 K)
Boiling point	184.13 °C (363.43 °F; 457.28 K)
Critical point (T, P)	698.8 K (425.7 °C), 4890 kPa
Solubility in water	3.6 g/(100 mL) at 20 °C
Vapor pressure	0.6 mmHg (20 °C)
Acidity (pKa)	4.63 (conjugate acid; H2O);
Magnetic susceptibility (χ)	−62.95·10−6 cm3/mol
Refractive index (nD)	1.58364
Viscosity	3.71 cP (3.71 mPa·s at 25 °C)
Thermochemistry
Heat capacity (C)	193.7 J/(mol K)
Std molar; entropy (S⦵298)	191 J/(mol K)
Std enthalpy of; formation (ΔfH⦵298)	31 kJ/mol
Std enthalpy of; combustion (ΔcH⦵298)	–3393 kJ/mol
Enthalpy of fusion (ΔfH⦵fus)	10.54 kJ/mol
Enthalpy of vaporization (ΔfHvap)	55.83 kJ/mol at 25 °C
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	potential occupational carcinogen
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H317, H318, H331, H341, H351, H372, H400
Precautionary statements	P201, 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, P501 Preview warning: Omit Rules: keep P260, omit P261
NFPA 704 (fire diamond)	3 2 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 h)
LCLo (lowest published)	250 ppm (rat, 4 h); 180 ppm (cat, 8 h)
	NIOSH (US health exposure limits):
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
	Aniline (data page)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Aniline (From Portuguese: anil, meaning 'indigo shrub', and -ine indicating a derived substance) is an organic compound with the formula C₆H₅NH₂. 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 (pK_aH = 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.