(S)-(+)-N-(2,3-Epoxypropyl)phthalimide
[CAS# 161596-47-0]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: (S)-(+)-N-(2,3-Epoxypropyl)phthalimide
• Synonyms: 2-[[(2S)-oxiran-2-yl]methyl]isoindole-1,3-dione
• Molecular Formula: C₁₁H₉NO₃
• Molecular Weight: 203.19
• CAS Registry Number: 161596-47-0
• EC Number: 454-720-9
• SMILES: C1[C@@H](O1)CN2C(=O)C3=CC=CC=C3C2=O

Properties

• Melting point: 102 °C

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08 Danger
• Risk Statements: H317-H318-H341
• Safety Statements: P203-P261-P264+P265-P272-P280-P302+P352-P305+P354+P338-P317-P318-P321-P333+P317-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Germ cell mutagenicity	Muta.	2	H341
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

(S)-(+)-N-(2,3-Epoxypropyl)phthalimide, with the chemical formula C11H9NO3, is an intriguing compound in organic chemistry, characterized by its unique structure which includes a phthalimide moiety and an epoxy group. The compound is notable for its utility in various chemical synthesis applications due to its reactivity and structural features.

The discovery of (S)-(+)-N-(2,3-Epoxypropyl)phthalimide is rooted in the exploration of phthalimide derivatives and their applications. Phthalimide itself has been studied extensively for its reactivity and utility as a precursor in organic synthesis. The introduction of the 2,3-epoxypropyl group to the phthalimide structure extends its application range by adding an epoxy functionality, which is known for its ability to undergo various chemical transformations.

The synthesis of (S)-(+)-N-(2,3-Epoxypropyl)phthalimide typically involves the reaction of phthalimide with an epoxypropyl halide. This reaction is facilitated under controlled conditions to ensure the formation of the desired epoxide group on the propyl chain. The stereochemistry of the product is controlled to achieve the (S)-enantiomer, which can be important for applications requiring specific chiral properties.

One of the primary applications of (S)-(+)-N-(2,3-Epoxypropyl)phthalimide is in the field of organic synthesis, particularly in the creation of complex molecules. The epoxy group in the compound serves as a reactive site for further chemical reactions, such as ring-opening reactions, which can be used to introduce various functional groups into the molecule. This reactivity is valuable for chemists working on the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.

In medicinal chemistry, (S)-(+)-N-(2,3-Epoxypropyl)phthalimide is utilized as an intermediate in the synthesis of bioactive compounds. The ability of the epoxy group to react with nucleophiles makes it useful in the creation of compounds with potential therapeutic properties. For example, the compound can be used to develop drugs with improved efficacy or selectivity by incorporating various functional groups into the final structure.

The compound also finds applications in polymer chemistry, where it can be used to modify polymer properties. The epoxy group allows for the introduction of new functionalities into polymers, potentially altering their physical and chemical properties. This modification is useful in developing advanced materials with specific characteristics, such as improved mechanical strength or enhanced chemical resistance.

Furthermore, (S)-(+)-N-(2,3-Epoxypropyl)phthalimide is valuable in research settings where it serves as a reagent or a building block for exploring new chemical reactions. Its ability to participate in diverse chemical transformations makes it a versatile tool for researchers investigating reaction mechanisms or developing new synthetic methodologies.

Overall, (S)-(+)-N-(2,3-Epoxypropyl)phthalimide is a significant compound in organic chemistry with diverse applications in synthesis, medicinal chemistry, and polymer science. Its unique structural features and reactivity make it a valuable intermediate and reagent in the development of new chemical entities and advanced materials.

References

2022. A Critical N-Nitrosamine Impurity of Anticoagulant Drug, Rivaroxaban: Synthesis, Characterization, Development of LC-MS/MS Method for Nanogram Level Quantification. Chromatographia, 85(2), 103-112.
DOI: 10.1007/s10337-021-04115-x

2021. Intramolecular Mitsunobu Cyclization of 1,5-Diols. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-137-00111

2020. Epoxides as Dual-Functionalized Alkylating Reagents in Catellani Reactions for the Assembly of Heterocycles. Synlett, 31(4), 395-400.
DOI: 10.1055/s-0039-1690779