N-Phenylacetamide (Acetanilide) CAS 99-15-0 98% White Crystalline Powder | Anilide / Amide Derivative for Organic Synthesis & Recrystallization Aid

1. Product Overview

N-Phenylacetamide (CAS 99-15-0), commonly known as acetanilide, has molecular formula C₈H₉NO and MW 135.17 g/mol. It is the N-acetyl derivative of aniline, consisting of a phenyl group linked to the nitrogen of acetamide. Acetanilide is used as a stable amide model substrate in hydrolysis/ rearrangement studies, as a precursor to aniline derivatives (via Hofmann or nitrosation routes), and historically as a recrystallization solvent modifier. The compound is stable, non-hygroscopic, and melts sharply near 114 °C, making it a useful melting-point reference.

2. Key Features and Benefits

• Stable Aromatic Amide: Resistant to hydrolysis under neutral conditions; cleaved by strong acid/base to aniline + acetate.

• Recrystallization Aid: Added in trace amounts to improve crystal habit or modify solubility behavior in organic recrystallizations.

• Aniline Protecting Group: Acetyl group masks –NH₂ of aniline; removed by acid or base hydrolysis when needed.

• High Purity Solid: Supplied ≥98% (HPLC), sharp mp suitable for melting point calibration in teaching labs.

• Synthetic Intermediate: Precursor to N-bromoacetanilide, p-nitroacetanilide (electrophilic aromatic substitution), and sulfa-drug analogs (research context only—no therapeutic claim).

3. Major Applications

• Organic Synthesis: Substrate for electrophilic aromatic substitution (nitration → p-nitroacetanilide, then deprotected), Beckmann-type rearrangements (after conversion to oxime), and aniline regeneration.

• Recrystallization / Solvent Modifier: Used in small quantities to influence nucleation and crystal growth in organic compound purification.

• Heterocycle Formation: Starting material for constructing quinazolines and benzoxazoles via cyclization with appropriate reagents.

• Analytical Reference: Standard for TLC/HPLC/mp verification in undergraduate and research settings.

• Method Development: Used in kinetics studies of amide hydrolysis and N-acylation/deacylation.

4. Technical Specifications

Item Description
Product Name N-Phenylacetamide (Acetanilide)
Synonyms Acetanilide; N-Acetylaniline; Phenylacetamide
CAS Number 99-15-0
Molecular Formula C₈H₉NO
Molecular Weight 135.17 g/mol
MDL Number MFCD00008536
PubChem CID 6209
Assay (Purity) ≥98% (HPLC)
Appearance White to faintly off-white crystalline flakes or powder
Melting Point 113–116 °C
Boiling Point 304 °C (Decomposes)
Density 1.121 g/cm³
Refractive Index n²⁰/D ≈ 1.586
Calculated LogP ~1.19
Polar Surface Area (PSA) 29.1 Ų
Hydrogen Bond Donors 1 (NH)
Hydrogen Bond Acceptors 2 (C=O, O)
Rotatable Bonds 1
Solubility Soluble in hot water (~5 g/100 mL at bp), ethanol, methanol, chloroform, ethyl acetate, DMSO; slightly soluble in cold water (~0.5 g/100 mL, 25 °C); insoluble in petroleum ether.
SMILES CC(=O)Nc1ccccc1
InChI Key DFCZYTRICFWZIT-UHFFFAOYSA-N
Storage RT, sealed, protect from moisture; stable ≥36 months
HS Code 2924.29.90 / 3822.90.00

5. Storage and Handling

Store in a tightly sealed container at room temperature, protected from excessive moisture. The compound is non-hygroscopic and chemically stable. Dissolve in hot water, ethanol, or other polar organic solvents for recrystallization or reactions. Hydrolysis to aniline + acetic acid requires heating with concentrated acid or base—carry out in fume hood. Standard PPE recommended.

6. Safety Summary

• GHS Classification: GHS07 – Warning

• Signal Word: Warning

• Hazard Statements: H302 (Harmful if swallowed), H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation)

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