15996-22-2

Basic information

• Product Name: 3,6-Methylene-2,5-piperazinedione
• Synonyms: 3,6-Methylene-2,5-piperazinedione;Cycloserine Impurity 5 (3,6-Dimethylene-2,5-piperazinedione);3,6-dimethylidenepiperazine-2,5-dione
• CAS NO: 15996-22-2
• Molecular Formula: C6H6N2O2
• Molecular Weight: 138.12404
• Product Categories: Amines, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 15996-22-2.mol

Chemical Properties

• Melting Point: >300 °C
• Boiling Point: 550.7°C at 760 mmHg
• Flash Point: 280.4°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 3.54E-12mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 12.17±0.20(Predicted)
• CAS DataBase Reference: 3,6-Methylene-2,5-piperazinedione(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-Methylene-2,5-piperazinedione(15996-22-2)
• EPA Substance Registry System: 3,6-Methylene-2,5-piperazinedione(15996-22-2)

Safety Data

• Hazardous Substances Data: 15996-22-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,6-Methylene-2,5-piperazinedione is used as an impurity in the production of Cycloserine (C988800), an antibacterial agent. Its presence is significant as it can impact the quality, safety, and efficacy of the final drug product. The pharmaceutical industry must monitor and control the levels of this impurity to ensure the therapeutic effectiveness and safety profile of Cycloserine.

InChI:InChI=1/C6H6N2O2/c1-3-5(9)8-4(2)6(10)7-3/h1-2H2,(H,7,10)(H,8,9)

Upstream product

• 5625-41-2 cyclo-serylserine 
• 5249-15-0 3,6-bis-acetoxymethyl-piperazine-2,5-dione 
• 16337-02-3 (3R,6R)-3,6-bis[(aminooxy)methyl]piperazine-2,5-dione 

Relevant articles and documents

An efficient and facile synthesis of D-cycloserine substantially free from potential impurities

An efficient and facile synthesis of D-cycloserine has been developed from D-serine with 61% overall yield employing protectiondeprotection strategy. Different parameters affecting the impurities content and yield of D-cycloserine have been studied. Mild reaction conditions provided the product with remarkable purity (>99%) and high stability.

Concise approach to the syntheses of (±)-gliocladin C and related diketopiperazine alkaloids

A unique approach to the diketopiperazine indole alkaloid (±)-gliocladin C was developed and applied to formal syntheses of the related alkaloids (±)-gliocladine C and (±)-T988C. The key features of the strategy include an unprecedented nucleophilic addition of a diketopiperazine to an isatin derivative followed by a Friedel-Crafts alkylation of the resultant tertiary alcohol with indole to establish the critical quaternary center. Subsequent reduction of the intermediate oxindole moiety and cyclization then delivered a pivotal hexahydropyrrolo[2,3-b]indole diketopiperazine intermediate that was readily converted into (±)-gliocladin C as well as racemic versions of key intermediates in the Overman syntheses of (+)-gliocladine C and (+)-T988C.