N-(Chloromethyl)phthalimide

N-(Chloromethyl)phthalimide (CAS No. 17564-64-6)

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1. Basic Information

IUPAC Name: 2-(Chloromethyl)isoindoline-1,3-dioneSynonyms:N-ChloromethylphthalimidePhthalimidomethyl chlorideCAS Number: 17564-64-6Molecular Formula: C₉H₆ClNO₂Molecular Weight: 195.60 g/molAppearance: White to off-white crystalline powderOdor: Odorless

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2. Physical and Chemical Properties

Property	Value
Melting Point	135–138°C (275–280°F)
Solubility	– Water: Insoluble
	– Organic solvents: Soluble in DMF, THF, chloroform
Stability	Moisture-sensitive (hydrolyzes slowly)

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3. Chemical Structure

      O        ║     ◯-N-CH₂-Cl        ║         O

(◯ = benzene ring fused at positions 1 & 2)

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4. Hazards (GHS Classification)

Acute Toxicity:Harmful if swallowed (H302)Causes skin irritation (H315)Causes serious eye irritation (H319)Sensitization: May cause allergic skin reaction (H317)Environmental: Toxic to aquatic life (H411)NFPA Rating: Health 2, Flammability 1, Reactivity 1

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5. Storage and Handling

Storage:Keep in airtight containers under inert gas (N₂)Store at 2–8°C protected from moistureHandling:Use nitrile gloves, face shield, and fume hoodAvoid contact with water/alcohols

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6. Applications

Organic Synthesis:Alkylating agent for amine protection (Emoc-type chemistry)Intermediate for pharmaceuticals (e.g., GABA analogs)Polymer Chemistry:Crosslinking agent for specialty resins

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