Acetanilide
An N-phenyl amide formed by acetylating aniline.
- Formula
- C8H9NO
- Functional group
- N-substituted amides
- Molar mass
- 135.16 g/mol
- Also known as
- N-phenylacetamide, Antifebrin, N-Acetylaniline, Acetanilid, Acetamidobenzene, Acetanil
Overview
An N-phenyl amide formed by acetylating aniline.
Its nitrogen is bonded to both phenyl and acetyl groups. Delocalisation into the carbonyl makes the nitrogen less available for protonation than in aniline. The remaining N–H bond distinguishes acetanilide from an N,N-disubstituted amide.
Identifiers
- Formula
- C8H9NO
- Functional group
- N-substituted amides
- Molar mass
- 135.16 g/mol
- Also known as
- N-phenylacetamide, Antifebrin, N-Acetylaniline, Acetanilid, Acetamidobenzene, Acetanil
Chemical identifiers
- SMILES
- CC(=O)NC1=CC=CC=C1
- InChI
- InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)
- PubChem CID
- 904
Properties
- Melting Point
- 114.3 °C
- Boiling Point
- 304 °C @ 760 MM HG
- Water solubility
- Water solubility= 6.93X10+3 mg/l at 25 °C
Data availability
Not published: Density.
Related compounds
- N-substituted amides
An N-phenyl amide formed by acetylating aniline.
Connected reactions
- 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: Acetanilide (CID 904)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- OpenStax Organic Chemistry: Chemistry of amidesJohn McMurry · OpenStax · 2023
Supports the qualitative structural interpretation of the recorded molecular structure; no new physical measurement or verified preparative yield is claimed.
- OpenStax Organic Chemistry: Reactions of aminesJohn McMurry · OpenStax · 2023
Supports the qualitative structure and reactivity context; identity and numerical measurements retain their original references.
- Hazardous Substances Data Bank (HSDB): Acetanilide — melting pointHazardous Substances Data Bank (HSDB)
Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/904#section=Melting-Point. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 76th ed. Boca Raton, FL: CRC Press Inc., 1995-1996., p. 3-5
- Hazardous Substances Data Bank (HSDB): Acetanilide — boiling pointHazardous Substances Data Bank (HSDB)
Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/904#section=Boiling-Point. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 76th ed. Boca Raton, FL: CRC Press Inc., 1995-1996., p. 3-5
- Hazardous Substances Data Bank (HSDB): Acetanilide — solubilityHazardous Substances Data Bank (HSDB)
Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/904#section=Solubility. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Yalkowsky SH, Dannenfelser RM; The Aquasol Database of Aqueous Solubility. Fifth ed, Tucson, AZ: Univ AZ, College of Pharmacy, PC Ver. (1992)