N-Hydroxyphthalimide
[CAS# 524-38-9]

Identification

• Classification: Biochemical >> Condensing agent
• Name: N-Hydroxyphthalimide
• Synonyms: Phthaloxime
• Molecular Formula: C₈H₅NO₃
• Molecular Weight: 163.13
• CAS Registry Number: 524-38-9
• EC Number: 208-358-1
• SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)O

Properties

• Density: 1.64 g/mL
• Melting point: 233-235 ºC (dec.)

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
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

N-Hydroxyphthalimide is a versatile compound known for its use in organic synthesis and as a reagent in various chemical processes. Its molecular formula is C8H5NO3, which combines the structure of phthalimide with a hydroxyl group, giving it unique properties that are valuable in a variety of applications.

N-Hydroxyphthalimide was first synthesized in the mid-20th century by chemists exploring novel functional groups and their applications. It is derived from phthalimide by the addition of a hydroxyl group to the nitrogen atom. This modification imparts a unique reactivity to the compound that makes it useful in a variety of chemical settings.

The compound features a hydroxyl group attached to the nitrogen of the phthalimide ring. This functional group enhances its reactivity in a variety of chemical transformations. N-Hydroxyphthalimide acts as a hydroxylating agent, forming stable intermediates in a variety of reactions.

N-Hydroxyphthalimide is widely used as a reagent in organic synthesis. It acts as a hydroxylating agent in reactions that introduce hydroxyl groups into substrates. This property is particularly valuable in the synthesis of pharmaceuticals and fine chemicals.

In oxidation chemistry, N-hydroxyphthalimide acts as a mild oxidant. It is used to oxidize a variety of organic substrates, including alcohols and aldehydes, and can be used to prepare compounds with higher oxidation states or complex synthetic pathways.

The compound is also used in free radical chemistry as a source of nitrogen-centered free radicals. These free radicals can initiate various polymerization reactions and participate in free radical-based transformations, making N-hydroxyphthalimide a useful tool in materials science and polymer chemistry.

In medicinal chemistry, N-hydroxyphthalimide is an intermediate in the synthesis of biologically active compounds. Its ability to precisely modify chemical structures is beneficial for the development of new drugs and therapeutic agents.

In analytical chemistry, N-hydroxyphthalimide is used to prepare derivatizing agents for chromatographic techniques. Its ability to form easily detectable derivatives aids in the analysis of complex mixtures.

The hydroxyl group in N-hydroxyphthalimide enhances its reactivity in a variety of chemical transformations, making it a versatile reagent. The ability of this compound to undergo selective oxidation makes it valuable in synthetic chemistry to make precise modifications to organic molecules. The use of N-Hydroxyphthalimide in organic synthesis, free radical chemistry, and pharmaceutical applications highlights its versatility and importance in multiple fields.

References

2023. Kinetic Laws of Oxidation of para-tert-Butylcumene in the Presence of N-Hydroxyphthalimide. Kinetics and Catalysis, 64(6).
DOI: 10.1134/s002315842306006x

2024. Insights into synthesis, reactivity, and biological activity of N-isoindoline-1, 3-diones heterocycles: a systematic literature review. Journal of the Iranian Chemical Society, 21(7).
DOI: 10.1007/s13738-024-03012-y

1983. Contact allergy to N-hydroxyphthalimide. Contact Dermatitis, 9(2).
DOI: 10.1111/j.1600-0536.1983.tb04641.x