aniline (CHEBI:17296)

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CHEBI:17296 - aniline

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ChEBI Name	aniline

ChEBI ID	CHEBI:17296

Definition	A primary arylamine in which an amino functional group is substituted for one of the benzene hydrogens.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:40796, CHEBI:2732, CHEBI:13834, CHEBI:22561

Supplier Information	ChemicalBook:CB7169544, ChemicalBook:CB7372142, eMolecules:477532, ZINC000017886255

Download	Molfile XML SDF

more structures >>

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Wikipedia	License
Aniline (from Portuguese anil '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 (pKaH = 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.
Read full article at Wikipedia

Formula

C6H7N

Net Charge

Average Mass

93.12650

Monoisotopic Mass

93.05785

InChI

InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2

InChIKey

PAYRUJLWNCNPSJ-UHFFFAOYSA-N

SMILES

Nc1ccccc1

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	aniline (CHEBI:17296) is a anilines (CHEBI:22562) aniline (CHEBI:17296) is a primary arylamine (CHEBI:50471)

Incoming	(2S,3S,4R,5R)-2-(4-aminophenyl)-5-hydroxymethylpyrrolidine-3,4-diol (CHEBI:45008) has functional parent aniline (CHEBI:17296) N-methylaniline (CHEBI:15733) has functional parent aniline (CHEBI:17296) anilide (CHEBI:13248) has functional parent aniline (CHEBI:17296) anilinyl (CHEBI:48372) has functional parent aniline (CHEBI:17296) benzenamine sulfate (CHEBI:61691) has functional parent aniline (CHEBI:17296) diethofencarb (CHEBI:4520) has functional parent aniline (CHEBI:17296) PAP (CHEBI:53758) has functional parent aniline (CHEBI:17296) pencycuron (CHEBI:7957) has functional parent aniline (CHEBI:17296) vorinostat (CHEBI:45716) has functional parent aniline (CHEBI:17296) anilino group (CHEBI:48285) is substituent group from aniline (CHEBI:17296)

IUPAC Name

aniline

Synonyms	Sources
aminobenzene	ChemIDplus
aminophen	ChemIDplus
Anilin	NIST Chemistry WebBook
Aniline	KEGG COMPOUND
ANILINE	PDBeChem
aniline	UniProt
Benzenamine	KEGG COMPOUND
benzeneamine	NIST Chemistry WebBook
kyanol	NIST Chemistry WebBook
Phenylamine	KEGG COMPOUND

Manual Xrefs	Databases
Aniline	Wikipedia
ANILINE	MetaCyc
ANL	PDBeChem
C00292	KEGG COMPOUND
DB06728	DrugBank
HMDB0003012	HMDB
View more database links

Registry Numbers	Types	Sources
2796	Gmelin Registry Number	Gmelin
605631	Reaxys Registry Number	Reaxys
62-53-3	CAS Registry Number	ChemIDplus
62-53-3	CAS Registry Number	NIST Chemistry WebBook

Citations

Chen H, Zhuang R, Yao J, Wang F, Qian Y, Masakorala K, Cai M, Liu H (2014)
Short-term effect of aniline on soil microbial activity: a combined study by isothermal microcalorimetry, glucose analysis, and enzyme assay techniques.
Environmental science and pollution research international 21, 674-683 [PubMed:23821252]
[show Abstract]

Uter W, Stropp G, Schnuch A, Lessmann H (2007)
Aniline--a 'historical' contact allergen? Current data from the IVDK and review of the literature.
The Annals of occupational hygiene 51, 219-226 [PubMed:17135213]
[show Abstract]

Wulferink M, González J, Goebel C, Gleichmann E (2001)
T cells ignore aniline, a prohapten, but respond to its reactive metabolites generated by phagocytes: possible implications for the pathogenesis of toxic oil syndrome.
Chemical research in toxicology 14, 389-397 [PubMed:11304127]
[show Abstract]
The most basic arylamine, aniline, belongs to a class of compounds notorious for inducing allergic and autoimmune reactions. In 1981 in Spain, many people succumbed to toxic oil syndrome (TOS), a disease caused by ingestion of cooking oil contaminated with aniline. Indirect evidence points toward an immune pathogenesis of TOS driven by T lymphocytes, but it is unclear to which antigens these cells could react. Here, using the popliteal lymph node (PLN) assay in mice, we analyzed the sensitizing potential of aniline, its metabolites, and some of the aniline-coupled lipids detected in the contaminated cooking oil. Whereas aniline itself and its non-protein-reactive metabolites nitrobenzene, p-aminophenol and N-acetyl-p-aminophenol, failed to elicit PLN responses, its reactive metabolites nitrosobenzene and N-hydroxylaniline did. The aniline-coupled lipids, namely, linoleic anilide and linolenic anilide, and a mixture of fatty acid esters of 3-(N-phenylamino)-1,2-propanediol, all implicated in TOS, induced significant PLN responses, whereas the respective aniline-free lipids, linoleic acid, linolenic acid, and triolein, did not. Hence, the aniline moiety plays a crucial role in the immunogenicity of the aniline-coupled lipids of TOS. PLN responses to the reactive aniline metabolites and the one aniline-coupled lipid that was tested, linolenic anilide, were T-cell-dependent. Secondary PLN responses to nitrosobenzene were detectable not only after priming with nitrosobenzene but, in some experiments, also after priming with linolenic anilide. This suggests that the aniline moiety was cleaved from the aniline-coupled lipid and metabolized to the intermediate nitrosobenzene that generated the prospective neoantigens. Consistent with this, in lymphocyte proliferation tests in vitro, T cells primed to nitrosobenzene reacted in anamnestic fashion to white bone marrow cells (WBMCs) pulsed with aniline. Hence, we propose that aniline is a prohapten that can be metabolized by WBMCs, which form neoantigens that are recognized by T cells. The possible significance of these findings for the pathogenesis of TOS is discussed.

el-Bayoumy K, Donahue JM, Hecht SS, Hoffmann D (1986)
Identification and quantitative determination of aniline and toluidines in human urine.
Cancer research 46, 6064-6067 [PubMed:3779628]
[show Abstract]

Marquet A, Larraga V, Diez JL, Amela C, Rodrigo J, Muñoz E, Pestaña A (1984)
Immunogenicity of fatty acid anilides in rabbits and the pathogenesis of the Spanish toxic oil syndrome.
Experientia 40, 977-980 [PubMed:6205897]
[show Abstract]

Last Modified

23 October 2015

General Comment
2014-02-06	Found in the urine samples of humans exposed to industrial aromatic amines.

ChEBI

CHEBI:17296 - aniline

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