3,6-Methylene-2,5-piperazinedione

Base Information

• Chemical Name: 3,6-Methylene-2,5-piperazinedione
• CAS No.: 15996-22-2
• Molecular Formula: C6H6 N2 O2
• Molecular Weight: 138.126
• Mol file: 15996-22-2.mol

Synonyms:2,5-Piperazinedione,3,6-dimethylene- (6CI,7CI,8CI); 2,5-Dimethylene-3,6-diketopiperazine;3,6-Dimethylene-2,5-piperazinedione; NSC 278175

Chemical Property of 3,6-Methylene-2,5-piperazinedione

Chemical Property:

• Vapor Pressure: 3.54E-12mmHg at 25°C
• Melting Point: >300 °C
• Boiling Point: 550.7°C at 760 mmHg
• PKA: 12.17±0.20(Predicted)
• Flash Point: 280.4°C
• PSA: 65.72000
• Density: 1.26g/cm³
• LogP: -2.11620
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

99%min ^*data from raw suppliers

3,6-Methylene-2,5-piperazinedione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3,6-Methylene-2,5-piperazinedione is an impurity of Cycloserine (C988800), an antibacterial agent.

Technology Process of 3,6-Methylene-2,5-piperazinedione

There total 4 articles about 3,6-Methylene-2,5-piperazinedione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

(3R,6R)-3,6-bis[(aminooxy)methyl]piperazine-2,5-dione (16337-02-3) → 3,6-dimethylidenepiperazine-2,5-dione (15996-22-2)

Guidance literature:

With sodium hydroxide; In water; at -5 - 30 ℃; for 20h;

DOI:10.1007/s10593-018-2197-y

Reference yield: 38.0%

3,6-bis-acetoxymethyl-piperazine-2,5-dione (5249-15-0) → 3,6-dimethylidenepiperazine-2,5-dione (15996-22-2)

Guidance literature:

With sodium t-butanolate; In N,N-dimethyl-formamide; Inert atmosphere;

DOI:10.1016/j.tet.2018.04.001

Reference yield:

cyclo-serylserine (5625-41-2,79617-26-8) → 3,6-dimethylidenepiperazine-2,5-dione (15996-22-2)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / Inert atmosphere

2: sodium t-butanolate / N,N-dimethyl-formamide / Inert atmosphere

With acetic acid; sodium t-butanolate; In N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2018.04.001

upstream raw materials:

(3R,6R)-3,6-bis[(aminooxy)methyl]piperazine-2,5-dione

cyclo-serylserine

3,6-bis-acetoxymethyl-piperazine-2,5-dione

Refernces

• 1、 Hodges, Timothy R.,Benjamin, Noah M.,Martin, Stephen F.. "Concise approach to the syntheses of (±)-gliocladin C and related diketopiperazine alkaloids". . p. 3329 - 3338. Retrieved 2018.