Phthalimide

Phthalimide
Other Names: 1H-Isoindole-1,3(2H)-dione, Isoindoline-1,3-dione
CAS Number: 85-41-6
Sum Formula: C₈H₅NO₂
Molar Mass: 147.13 g/mol
Appearance: White to off-white crystalline powder

Phthalimide is a cyclic imide compound derived from phthalic acid. It is widely used as an intermediate in organic synthesis, particularly in the Gabriel synthesis of primary amines, and as a precursor to various agrochemicals, dyes, and specialty materials. It is valued for its thermal stability and reactivity with nucleophiles.

Chemical and Physical Properties
Density: 1.21 g/cm³
Melting Point: 229–231°C
Boiling Point: Decomposes before boiling
Solubility in Water: Poorly soluble (~0.06 g/100 mL at 25°C)
Solubility in Organic Solvents: Soluble in hot ethanol, acetone, DMSO, and alkaline solutions
Odor: Odorless or faint
Stability: Stable under dry, ambient conditions

Applications
Used in the Gabriel synthesis for producing primary amines
Intermediate in the synthesis of dyes, pigments, agrochemicals, and polymers
Precursor to N-substituted phthalimides and other nitrogen-containing compounds
Employed as a building block in laboratory organic chemistry
Used in industrial formulation chemistry as a non-volatile nitrogen donor

Safety

First Aid Measures
Eye Contact: Rinse with water for several minutes. Seek medical attention if irritation develops
Skin Contact: Wash with soap and water
Inhalation: Move to fresh air. Seek medical attention if symptoms occur
Ingestion: Rinse mouth. Do not induce vomiting. Seek medical help if unwell

Handling and Storage
Store in a cool, dry, well-ventilated area
Keep container tightly closed and away from incompatible materials such as strong oxidizers
Avoid generating or inhaling dust during handling
Use appropriate PPE in workplace environments