N-Chlorophthalimide
[CAS# 3481-09-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Imide
• Name: N-Chlorophthalimide
• Synonyms: NCP; Phthalimide chloride; Phthalimidoyl chloride; 2-Chloro-1H-isoindole-1,3(2H)-dione
• Molecular Formula: C₈H₄ClNO₂
• Molecular Weight: 181.58
• CAS Registry Number: 3481-09-2
• EC Number: 222-459-8
• SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)Cl

Properties

• Melting point: 188-198 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318

Discovory and Applicatios

N-Chlorophthalimide (NCP) is an organic compound that has found use in a variety of chemical and industrial applications as a chlorinating and oxidizing agent. The compound is derived from phthalimide, a versatile precursor in organic synthesis.

N-Chlorophthalimide was first synthesized in the early 20th century as part of a broad exploration of N-haloimides, a class of compounds with reactive halogen atoms. The synthesis of NCP involves the chlorination of phthalimide, typically using chlorine gas or sodium hypochlorite. This process introduces a chlorine atom into the nitrogen atom of the phthalimide ring to form NCP.

The primary use of N-Chlorophthalimide is as a chlorinating agent in organic synthesis, introducing chlorine atoms into various organic molecules and facilitating the synthesis of chlorinated compounds, which are essential intermediates in pharmaceuticals, agrochemicals, and dyes. NCP provides more controlled and selective chlorination than other chlorinating agents.

NCPs can also be used as oxidants. Its ability to transfer oxygen atoms makes it very useful in oxidative transformations, such as the conversion of alcohols to carbonyl compounds (aldehydes and ketones). This property is particularly useful in synthetic organic chemistry, where selective oxidation is often required.

Due to its chlorinating properties, N-chlorophthalimide exhibits antimicrobial activity. It has been studied for its potential use as a disinfectant and preservative. Its ability to inactivate microorganisms makes it a candidate for hygienic and sanitary applications, especially in environments where effective microbial control is required.

In polymer chemistry, NCPs are used as initiators for free radical polymerization reactions. It initiates the polymerization process through free radical generation, which helps to form polymers with specific structures and properties. This application is of great significance in the production of various plastic materials and coatings.

N-chlorophthalimide is used in analytical chemistry as a reagent for the detection and quantification of certain functional groups in organic compounds. Its reactivity with specific groups allows the development of analytical methods and assays that can identify and measure the presence of target compounds in complex mixtures.

N-Chlorophthalimide offers several advantages in its applications: It provides selective chlorination and oxidation with reduced risk of undesirable side reactions. NCP is relatively stable under standard conditions and is easier to handle and store than other reactive chlorinating agents. Its small dosage makes it a cost-effective choice for large-scale industrial processes.