N-Hydroxyethylphthalimide
[CAS# 3891-07-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Imide
• Name: N-Hydroxyethylphthalimide
• Synonyms: N-(2-Hydroxyethyl)phthalimide; 2-(2-Hydroxyethyl)-1H-isoindole-1,3(2H)-dione
• Molecular Formula: C₁₀H₉NO₃
• Molecular Weight: 191.19
• CAS Registry Number: 3891-07-4
• EC Number: 223-434-4
• SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)CCO

Properties

• Melting point: 126-129 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety 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
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2B	H320
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

N-Hydroxyethylphthalimide (N-HEPh) is a compound with a wide range of applications in organic synthesis and pharmaceuticals. This substance is derived from the reaction of phthalimide with hydroxyethylamine and has become a useful tool in various chemical processes due to its unique reactivity and stability.

N-Hydroxyethylphthalimide was first synthesized in the mid-20th century as part of research to develop new organic synthesis reagents. The compound is prepared by the reaction of phthalimide with hydroxyethylamine, a process that introduces a hydroxyethyl group into the phthalimide structure. The reaction involves a nucleophilic substitution in which the hydroxyethyl group replaces a hydrogen atom in the phthalimide structure to form an N-hydroxyethyl derivative.

N-Hydroxyethylphthalimide is primarily used as an organic synthesis reagent. It is a powerful nucleophile that can be used in a variety of reactions to introduce hydroxyethyl groups into target molecules. This feature is very useful for modifying and creating complex organic compounds with specific properties.

In the pharmaceutical industry, N-Hydroxyethylphthalimide is a key intermediate in the synthesis of various drugs. Its role in introducing functional groups makes it an essential material for the development of pharmaceutical compounds with increased efficacy and selectivity, especially for the synthesis of compounds that require precise structural modifications.

Researchers use N-hydroxyethylphthalimide to study reaction mechanisms and explore new synthetic routes. Its unique properties and reactivity provide insights into the behavior of phthalimide derivatives, contributing to the advancement of chemical knowledge and the development of new synthetic methods.

In agrochemical formulations, N-hydroxyethylphthalimide is used as an intermediate in the production of herbicides and insecticides. Its ability to modify chemical structures makes it useful for the manufacture of agrochemicals with enhanced activity and selectivity against pests and weeds.

The versatility of N-hydroxyethylphthalimide as a reagent makes it valuable in a variety of chemical reactions. It can participate in a variety of reactions, including nucleophilic substitution and functional group transformation, which enhances its utility in organic synthesis. The introduction of hydroxyethyl groups via N-hydroxyethylphthalimide can improve the functionalization of organic molecules. This modification can improve properties such as solubility and reactivity, which are beneficial for pharmaceutical and agrochemical applications. N-Hydroxyethylphthalimide exhibits good stability under typical laboratory conditions, making it a reliable reagent for a variety of synthetic processes. Its reactivity is well characterized, resulting in predictable results in chemical reactions.

References

2019. The phthalimide analogues N-3-hydroxypropylphthalimide and N-carboxymethyl-3-nitrophthalimide exhibit activity in experimental models of inflammatory and neuropathic pain. Pharmacological reports : PR, 71(6).
DOI: 10.1016/j.pharep.2019.08.001

2009. Synthesis, characterization, and application of novel biodegradable self-assembled 2-(N-phthalimido) ethyl-palmitate nanoparticles for cancer therapy. Journal of Nanoparticle Research, 11(6).
DOI: 10.1007/s11051-009-9754-3

2006. 2-(2-Hydroxyethyl)isoindoline-1,3-dione. Acta Crystallographica Section E Structure Reports Online, 62(10).
DOI: 10.1107/s1600536806035367