Aniline
Phenylamine, an aromatic amine used to compare nitrogen basicity.
- Formula
- C6H7N
- Functional group
- Aromatic amines
- Molar mass
- 93.13 g/mol
- Also known as
- Benzenamine, Phenylamine, Aminobenzene, Aminophen, Arylamine, Kyanol
Overview
Phenylamine, an aromatic amine used to compare nitrogen basicity.
The nitrogen lone pair interacts with the aromatic ring, making it less available for protonation than in an alkylamine. Aniline still forms an anilinium salt with an appropriate acid. Compare conjugate-acid equilibria rather than assuming every NH2-containing molecule has the same basicity.
Identifiers
- Formula
- C6H7N
- Functional group
- Aromatic amines
- Molar mass
- 93.13 g/mol
- Also known as
- Benzenamine, Phenylamine, Aminobenzene, Aminophen, Arylamine, Kyanol
Chemical identifiers
- SMILES
- C1=CC=C(C=C1)N
- InChI
- InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
- PubChem CID
- 6115
Properties
- Melting Point
- -6.0 °C
- Boiling Point
- 184.1 °C
- Relative density (water = 1)
- Relative density (water = 1): 1.02
- Water solubility
- In water, 36,000 mg/L at 25 °C
Related compounds
- Aromatic amines
Phenylamine, an aromatic amine used to compare nitrogen basicity.
Connected reactions
- Nitro reduction and basification: Nitrobenzene → Aniline
Nitrobenzene gives aniline through nitro reduction and basification.
- N acetylation: Aniline → Acetanilide
The aniline nitrogen attacks an anhydride carbonyl and displaces an acetate-derived leaving group. Proton transfer forms acetanilide and ethanoic acid; attachment to C=O makes the product nitrogen an amide nitrogen.
References
- PubChem Compound Summary: Aniline (CID 6115)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- OpenStax Organic Chemistry: Basicity of aminesJohn McMurry · OpenStax · 2023
Supports the qualitative structural interpretation of the recorded molecular structure; no new physical measurement or verified preparative yield is claimed.
- Hazardous Substances Data Bank (HSDB): Aniline — melting pointHazardous Substances Data Bank (HSDB)
Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/6115#section=Melting-Point. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 3-28
- Hazardous Substances Data Bank (HSDB): Aniline — boiling pointHazardous Substances Data Bank (HSDB)
Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/6115#section=Boiling-Point. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 3-28
- ILO-WHO International Chemical Safety Cards (ICSCs): Aniline — densityILO-WHO International Chemical Safety Cards (ICSCs)
Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/6115#section=Density. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred.
- Hazardous Substances Data Bank (HSDB): Aniline — solubilityHazardous Substances Data Bank (HSDB)
Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/6115#section=Solubility. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Yalkowsky, S.H., He, Yan, Jain, P. Handbook of Aqueous Solubility Data Second Edition. CRC Press, Boca Raton, FL 2010, p. 259