Aniline

Title: Aniline
CAS Registry Number: 62-53-3
CAS Name: Benzenamine
Additional Names: aniline oil; phenylamine; aminobenzene; aminophen; kyanol
Molecular Formula: C6H7N
Molecular Weight: 93.13
Percent Composition: C 77.38%, H 7.58%, N 15.04%
Literature References: First obtained in 1826 by Unverdorben from dry distillation of indigo. Runge found it in coal tar in 1834. Fritzsche, in 1841, prepared it from indigo and potash and gave it the name aniline. Manuf from nitrobenzene or chlorobenzene: Faith, Keyes & Clark's Industrial Chemicals, F. A. Lowenheim, M. K. Moran, Eds. (Wiley-Interscience, New York, 4th ed., 1975) pp 109-116. Procedures: A. I. Vogel, Practical Organic Chemistry (Longmans, London, 3rd ed., 1959) p 564; Gattermann-Wieland, Praxis des Organischen Chemikers (de Gruyter, Berlin, 40th ed., 1961) p 148. Brochure "Aniline" by Allied Chemical's National Aniline Division (New York, 1964) 109 pp, gives reactions and uses of aniline (877 references). Toxicity study: K. H. Jacobson, Toxicol. Appl. Pharmacol. 22, 153 (1972).
Properties: Oily liquid; colorless when freshly distilled, darkens on exposure to air and light. Poisonous! Characteristic odor and burning taste; combustible; volatile with steam. d2020 1.022. bp 184-186°. Solidif -6°. Flash pt, closed cup: 169°F (76°C). nD20 1.5863. pKb 9.30. pH of 0.2 molar aq soln 8.1. One gram dissolves in 28.6 ml water, 15.7 ml boil. water; misc with alcohol, benzene, chloroform, and most other organic solvents. Combines with acids to form salts. It dissolves alkali or alkaline earth metals with evolution of hydrogen and formation of anilides, e.g., C6H5NHNa. Keep well closed and protected from light. Incompat. Oxidizers, albumin, solns of Fe, Zn, Al, acids, and alkalies. LD50 orally in rats: 0.44 g/kg (Jacobson).
Boiling point: bp 184-186°
Flash point: Flash pt, closed cup: 169°F (76°C)
pKa: pKb 9.30
Index of refraction: nD20 1.5863
Density: d2020 1.022
Toxicity data: LD50 orally in rats: 0.44 g/kg (Jacobson)
Derivative Type: Hydrobromide
Molecular Formula: C6H7N.HBr
Molecular Weight: 174.04
Percent Composition: C 41.41%, H 4.63%, N 8.05%, Br 45.91%
Properties: White to slightly reddish, crystalline powder, mp 286°. Darkens in air and light. Sol in water, alc. Protect from light.
Melting point: mp 286°
Derivative Type: Hydrochloride
Molecular Formula: C6H7N.HCl
Molecular Weight: 129.59
Percent Composition: C 55.61%, H 6.22%, N 10.81%, Cl 27.36%
Properties: Crystals, mp 198°. d 1.222. Darkens in air and light. Sol in about 1 part water; freely sol in alc. Protect from light.
Melting point: mp 198°
Density: d 1.222
Derivative Type: Hydrofluoride
Molecular Formula: C6H7N.HF
Molecular Weight: 113.13
Percent Composition: C 63.70%, H 7.13%, N 12.38%, F 16.79%
Properties: Crystalline powder. Turns gray on standing. Freely sol in water; slightly sol in cold, freely in hot alc.
Derivative Type: Nitrate
Molecular Formula: C6H7N.HNO3
Molecular Weight: 156.14
Percent Composition: C 46.15%, H 5.16%, N 17.94%, O 30.74%
Properties: Crystals, dec about 190°. d 1.36. Discolors in air and light. Sol in water, alc. Protect from light.
Density: d 1.36
Derivative Type: Hemisulfate
Molecular Formula: C5H7N.½H2SO4
Molecular Weight: 130.16
Percent Composition: C 46.14%, H 6.20%, N 10.76%, S 12.32%, O 24.58%
Properties: Crystalline powder. d 1.38. Darkens on exposure to air and light. One gram dissolves in about 15 ml water; slightly sol in alc. Practically insol in ether. Protect from light.
Density: d 1.38
Derivative Type: Acetate
Molecular Formula: C6H5NH2.HOOCCH3
Molecular Weight: 153.18
Percent Composition: C 62.73%, H 7.24%, N 9.14%, O 20.89%
Properties: Prepd from aniline and acetic acid: Vignon, Evieux, Bull. Soc. Chim. Fr. [4] 3, 1012 (1908). Colorless liquid. d 1.070-1.072. Darkens with age; gradually converted to acetanilide on standing. Misc with water, alc.
Density: d 1.070-1.072
Derivative Type: Oxalate
Molecular Formula: C6H5NH2.HOOCCOOH.H2NC6H5
Molecular Weight: 276.29
Percent Composition: C 60.86%, H 5.84%, N 10.14%, O 23.16%
Properties: Prepd from aniline and oxalic acid in alc soln: Hofmann, Ann. 47, 37 (1843). Triclinic rods from water, mp 174-175°. Readily sol in water; sparingly sol in abs alc. Practically insol in ether.
Melting point: mp 174-175°
CAUTION: Poisoning may occur from inhalation, skin penetration or ingestion. Potential symptoms of overexposure are navy blue to black lips, tongue, mucous membranes; slate gray skin; headache, nausea, vomiting, confusion, ataxia, vertigo, tinnitus, weakness, disorientation, lethargy, drowsiness; dyspnea on effort; methemoglobinemia, cyanosis, coma; tachycardia, heart blocks, arryhthmia, shock; painful micturition, hematuria, hemoglobinuria, methemoglobinuria, oliguria, renal insufficiency; cirrhosis. Direct contact may cause eye irritation. Potential occupational carcinogen. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 18; Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section III, pp 31-36.
Use: Manuf dyes, medicinals, resins, varnishes, perfumes, shoe blacks; vulcanizing rubber; as solvent. Hydrochloride used in manuf of intermediates, aniline black and other dyes, in dyeing fabrics or wood black.
Aniline Mustard Anilinephthalein Anise Alcohol Anisidine Anisindione

Aniline
Aniline Aniline
Space-filling model of solid aniline
Identifiers
CAS number 62-53-3 YesY
ChemSpider 5889 YesY
UNII SIR7XX2F1K YesY
DrugBank DB06728
KEGG C00292 YesY
ChEBI CHEBI:17296 YesY
ChEMBL CHEMBL538 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C6H5NH2
Molar mass 93.13 g/mol
Appearance colorless to yellow liquid
Density 1.0217 g/mL, liquid
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
Basicity (pKb) 9.3
Viscosity 3.71 cP (3.71 mPa·s at 25 °C
Thermochemistry
Std enthalpy of
combustion ΔcHo298
-3394 kJ/mol
Hazards
MSDS External MSDS
EU classification Toxic (T)
Carc. Cat. 3
Muta. Cat. 3
Dangerous for
the environment (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
NFPA 704.svg
2
3
0
Flash point 70 °C; 158 °F; 343 K
Autoignition temperature 770 °C; 1,420 °F; 1,040 K
Related compounds
Related aromatic amines 1-Naphthylamine
2-Naphthylamine
Related compounds Phenylhydrazine
Nitrosobenzene
Nitrobenzene
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to polyurethane. Like most volatile amines, it possesses the somewhat unpleasant odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds.