Record Information
Version1.0
Creation date2010-04-08 22:05:51 UTC
Update date2019-11-27 17:09:40 UTC
Primary IDFDB003571
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAniline
DescriptionAniline is a weak base. Aromatic amines such as aniline are, in general, much weaker bases than aliphatic amines. Aniline reacts with strong acids to form anilinium (or phenylammonium) ion (C6H5-NH3+). The sulfate forms beautiful white plates. Although aniline is weakly basic, it precipitates zinc, aluminium, and ferric salts, and, on warming, expels ammonia from its salts. The weak basicity is due to a negative inductive effect as the lone pair on the nitrogen is partially delocalised into the pi system of the benzene ring.; Aniline is an organic chemical compound, specifically a primary aromatic amine. It consists of a benzene ring attached to an amino group. Aniline is oily and, although colorless, it can be slowly oxidized and resinified in air to form impurities which can give it a red-brown tint. Its boiling point is 184 degree centigrade and its melting point is -6 degree centegrade. It is a liquid at room temperature. Like most volatile amines, it possesses a somewhat unpleasant odour of rotten fish, and also has a burning aromatic taste; Aniline was first isolated from the destructive distillation of indigo in 1826 by Otto Unverdorben , who named it crystalline. In 1834, Friedrich Runge (Pogg. Ann., 1834, 31, p. 65; 32, p. 331) isolated from coal tar a substance that produced a beautiful blue colour on treatment with chloride of lime, which he named kyanol or cyanol. In 1841, C. J. Fritzsche showed that, by treating indigo with caustic potash, it yielded an oil, which he named aniline, from the specific name of one of the indigo-yielding plants, Indigofera anil, anil being derived from the Sanskrit n?la, dark-blue, and n?l?, the indigo plant. About the same time N. N. Zinin found that, on reducing nitrobenzene, a base was formed, which he named benzidam. August Wilhelm von Hofmann investigated these variously-prepared substances, and proved them to be identical (1855), and thenceforth they took their place as one body, under the name aniline or phenylamine.; Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H7N. It is the simplest and one of the most important aromatic amines, being used as a precursor to more complex chemicals. Its main application is in the manufacture of polyurethane. Like most volatile amines, it possesses the somewhat unpleasant odour of rotten fish and also has a burning aromatic taste; it is a highly-acrid poison. It ignites readily, burning with a smoky flame.; Like phenols, aniline derivatives are highly susceptible to electrophilic substitution reactions. For example, reaction of aniline with sulfuric acid at 180 °C produces sulfanilic acid, NH2C6H4SO3H, which can be converted to sulfanilamide. Sulfanilamide is one of the sulfa drugs that were widely used as antibacterials in the early 20th century.; The great commercial value of aniline was due to the readiness with which it yields, directly or indirectly, dyestuffs. The discovery of mauve in 1856 by William Henry Perkin was the first of a series of an enormous range of dyestuffs, such as fuchsine, safranine and induline. In addition to its use as a precursor to dyestuffs, it is a starting-product for the manufacture of many drugs, such as paracetamol (acetaminophen, Tylenol).; it is a highly acrid poison. It ignites readily, burning with a large smoky flame. Aniline reacts with strong acids to form salts containing the anilinium (or phenylammonium) ion (C6H5-NH3+), and reacts with acyl halides (such as acetyl chloride (ethanoyl chloride), CH3COCl) to form amides. The amides formed from aniline are sometimes called anilides, for example CH3-CO-NH-C6H5 is acetanilide, for which the modern name is N-phenyl ethanamide. Like phenols, aniline derivatives are highly reactive in electrophilic substitution reactions. For example, sulfonation of aniline produces sulfanilic acid, which can be converted to sulfanilamide. Sulfanilamide is one of the sulfa drugs which were widely used as antibacterial in the early 20th century. Aniline was first isolated from the destructive distillation of indigo in 1826 by Otto Unverdorben. In 1834, Friedrich Runge isolated from coal tar a substance which produced a beautiful blue color on treatment with chloride of lime; this he named kyanol or cyanol. In 1841, C. J. Fritzsche showed that by treating indigo with caustic potash it yielded an oil, which he named aniline, from the specific name of one of the indigo-yielding plants, Indigofera anil, anil being derived from the Sanskrit, dark-blue. Aniline is found in many foods, some of which are corn, tea, white cabbage, and cabbage.
CAS Number62-53-3
Structure
Thumb
Synonyms
SynonymSource
AminobenzeneChEBI
AminophenChEBI
AnilinChEBI
BenzenamineChEBI
BenzeneamineChEBI
KyanolChEBI
PhenylamineChEBI
ArylamineKegg
AnilinaHMDB
Aniline hydrobromideHMDB
Aniline reagentHMDB
AnyvimHMDB
BenzidamHMDB
CyanolHMDB
D'AnilineHMDB
KrystallinHMDB
Aniline diphosphate (3:1)HMDB
Aniline hydrogen iodideHMDB
Aniline phosphate (1:2)HMDB
Aniline phosphate (2:1)HMDB
Aniline sulfateHMDB
Aniline, 3-(13)C-labeled CPDHMDB
Aniline aluminium saltHMDB
Aniline diphosphate (4:1)HMDB
Aniline hydrochloride-(15)N-labeled CPDHMDB
Aniline hydrofluorideHMDB
Aniline monosulfateHMDB
Aniline nitrateHMDB
Aniline sulfate (2:1)HMDB
Aniline, 2-(13)C-labeled CPDHMDB
Aniline, conjugate acidHMDB
Aniline, sodium saltHMDB
Aniline dihydrofluorideHMDB
Aniline diphosphate (1:1)HMDB
Aniline hydrochlorideHMDB
Aniline hydrochloride-(14)C-labeled CPDHMDB
Aniline perchlorateHMDB
Aniline phosphonate (1:1)HMDB
Aniline, (13)C-labeled CPDHMDB
Aniline, (14)C-labeled CPDHMDB
Aniline, 4-(13)C-labeled CPDHMDB
Aniline, ion(1+)HMDB
Aniline, monolithium saltHMDB
Aniline phosphate (1:1)HMDB
Aniline sulfate (2:1), (14)C-labeled CPDHMDB
Aniline, 15N-labeled CPDHMDB
Aniline, 3H-labeled CPDHMDB
Aniline, magnesium (1:1) saltHMDB
2424-53-5 (monosulfate)biospider
542-11-0 (hydrobromide)biospider
Aniline (and salts)biospider
ANILINE (SEE ALSO ANILINE HYDROCHOLORIDE 142-04-1)biospider
Aniline [UN1547] [Poison]biospider
Aniline and homologsbiospider
Aniline and homologuesbiospider
Aniline oilbiospider
Aniline oil, phenylaminebiospider
ANILINE- 2,3,4,5,6-D5biospider
Aniline, acsbiospider
Aniline(S#299)-Liqbiospider
Anilinumbiospider
Aromatic aminebiospider
Benzaminebiospider
Benzene, aminobiospider
Benzene, amino-biospider
Benzene,amino (aniline)biospider
Blue oilbiospider
C.I. Oxidation base 1biospider
CI Oxidation Base 1biospider
HSDB 43biospider
Phenyleneaminebiospider
Predicted Properties
PropertyValueSource
Water Solubility18 g/LALOGPS
logP0.89ALOGPS
logP1.14ChemAxon
logS-0.71ALOGPS
pKa (Strongest Basic)4.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.76 m³·mol⁻¹ChemAxon
Polarizability10.29 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H7N
IUPAC nameaniline
InChI IdentifierInChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
InChI KeyPAYRUJLWNCNPSJ-UHFFFAOYSA-N
Isomeric SMILESNC1=CC=CC=C1
Average Molecular Weight93.1265
Monoisotopic Molecular Weight93.057849229
Classification
Description belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAniline and substituted anilines
Direct ParentAniline and substituted anilines
Alternative Parents
Substituents
  • Aniline or substituted anilines
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point-6 oC
Boiling PointNot Available
Experimental Water Solubility36 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP0.90HANSCH,C ET AL. (1995)
Experimental pKa4.6
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-9a543eee5081cc927e82View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e04550d3cafee77e6192View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-b4213ef5f8ee4a3df612View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1900000000-b5d970641bbe63fdb366View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-9a543eee5081cc927e82View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e04550d3cafee77e6192View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-b4213ef5f8ee4a3df612View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1900000000-b5d970641bbe63fdb366View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-62eb000567821fbe8a22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-0900000000-ed34a4f0bafc3ce06174View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9000000000-a23bad3a5415210b8e58View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-129ed2147aba87164399View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-9000000000-9e60a29bae11a3beb396View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-00kf-9000000000-8e5e6fec72fd720bd3bbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0006-9000000000-e04550d3cafee77e6192View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-9000000000-4a2ea8998eab06e3b7faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-002f-9000000000-041fc0d729e6308b36ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-004i-9000000000-c0f67277e0af76d5d6e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0fb9-9000000000-35b2093eb2c81ba07d17View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9000000000-15d86b7cf94658003a7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-03di-9000000000-fc34fd188d386065c4f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-03dl-9000000000-fbed3991af3afeea3a79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9000000000-0bea53746f5bc30ab770View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0007-9000000000-971619ea8bd73637ba14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-2001822055db683e8999View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0006-9000000000-a5bc25b5010f2044b435View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0006-9000000000-8ab282b725391b0d9923View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-4a2ea8998eab06e3b7faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-002f-9000000000-041fc0d729e6308b36ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-c0f67277e0af76d5d6e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fb9-9000000000-35b2093eb2c81ba07d17View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-15d86b7cf94658003a7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-9000000000-fc34fd188d386065c4f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03dl-9000000000-fbed3991af3afeea3a79View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00kf-9000000000-4ba5d22a406245826ca0View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID5889
ChEMBL IDCHEMBL538
KEGG Compound IDC00292
Pubchem Compound ID6115
Pubchem Substance IDNot Available
ChEBI ID17296
Phenol-Explorer IDNot Available
DrugBank IDDB06728
HMDB IDHMDB03012
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDANILINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDANL
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAniline
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Arylamine N-acetyltransferase 1NAT1P18440
Arylamine N-acetyltransferase 2NAT2P11245
Arylacetamide deacetylaseAADACP22760
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).