File:Structural_formula_of_aniline.svg · Wikimedia Commons · See Wikimedia Commons
aniline
Sign in to saveAlso known as Aminobenzene, Aniline oil, Benzenamine, Phenylamine, Aminophen, Anyvim, Benzidam, Blue Oil
Aniline (From , meaning 'indigo shrub', and -ine indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), 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
Aniline is a simple organic chemical made of a phenyl group attached to an amino group, and it serves as a starting material for producing polyurethane, dyes, and other important industrial chemicals. It's an industrially significant commodity chemical that smells like rotten fish and ignites easily when exposed to flame.
AI-generated from the Wikipedia summary — may contain errors.
Chemical data
- Formula
- C6H7N
- Molecular weight
- 93.13 g/mol
- IUPAC name
- aniline
- SMILES
- C1=CC=C(C=C1)N
- InChIKey
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N
- XLogP
- 0.9
- Polar surface area
- 26 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Has part
- nitrogen
- Mass
- 93.058
- Autonomy
- 615
Show 22 more facts
- Commons category
- Aniline
- chemical formula
- C₆H₇N
- melting point
- -6
- NIOSH Pocket Guide ID
- 0033
- density
- 1.02
- immediately dangerous to life or health
- 381
- boiling point
- 184.17
- vapor pressure
- 0.6
- flash point
- 76
- solubility
- 34
- lower flammable limit
- 1.3
- upper flammable limit
- 11
- ionization energy
- 7.72
- time-weighted average exposure limit
- 5
- found in taxon
- Trigonella foenum-graecum
- ceiling exposure limit
- 0
- minimal lethal dose
- 150
- median lethal dose (LD50)
- 250
- short-term exposure limit
- 2
- canonical SMILES
- C1=CC=C(C=C1)N
- discoverer or inventor
- Nikolay Zinin
- electric dipole moment
- 1.13
Sources (7)
via Wikidata · CC0
~17 min read
Encyclopedic overview
25 sectionsContents
- Structure
- Aryl-N distances
- Pyramidalization
- Production
- Related aniline derivatives
- Reactions
- Oxidation
- Electrophilic reactions at ortho- and para- positions
- Reactions at nitrogen
- Basicity
- Acylation
- ''N''-Alkylation
- Carbon disulfide derivatives
- Diazotization
- Other reactions
- Uses
- History
- Synthetic dye industry
- Developments in medicine
- Rocket fuel
- Toxicology and testing
- Oxidative DNA damage
- Notes
- References
- External links
Aniline (From , meaning 'indigo shrub', and -ine indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), 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.
Excerpted from Wikipedia’s “aniline” article, available under the CC BY-SA 4.0 licence.