5625-41-2

Basic information

• Product Name: 3,6-BIS(HYDROXYMETHYL)-2,5-PIPERAZINEDIONE
• Synonyms: 3,6-BIS(HYDROXYMETHYL)-2,5-PIPERAZINEDIONE;2,5-Piperazinedione,3,6-bis(hydroxymethyl)-(6CI,7CI,8CI,9CI);3,6-BIS(HYDROXYMETHYL)PIPERAZINE-2,5-DIONE;Nsc508753
• CAS NO: 5625-41-2
• Molecular Formula: C₆H₁₀N₂O₄
• Molecular Weight: 174.15
• Product Categories: PIPERIDINE
• Mol File: 5625-41-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 224 °C
• Boiling Point: 675°Cat760mmHg
• Flash Point: 362°C
• Appearance: /
• Density: 1.353g/cm³
• Vapor Pressure: 4.09E-21mmHg at 25°C
• Refractive Index: 1.5
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 11.84±0.60(Predicted)
• CAS DataBase Reference: 3,6-BIS(HYDROXYMETHYL)-2,5-PIPERAZINEDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-BIS(HYDROXYMETHYL)-2,5-PIPERAZINEDIONE(5625-41-2)
• EPA Substance Registry System: 3,6-BIS(HYDROXYMETHYL)-2,5-PIPERAZINEDIONE(5625-41-2)

Safety Data

• Hazardous Substances Data: 5625-41-2(Hazardous Substances Data)

Usage

Uses

3,6-Bis(hydroxymethyl)-2,5-piperazinedione is an intermediate in the synthesis of impurities of Cycloserine (C988800), an antibacterial agent.

InChI:InChI=1/C6H10N2O4/c9-1-3-5(11)8-4(2-10)6(12)7-3/h3-4,9-10H,1-2H2,(H,7,12)(H,8,11)/t3-,4-/m0/s1

Upstream product

• 2788-84-3 (S)-serine methyl ester 
• 2104-89-4 Ser-OMe 
• 5680-80-8 methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride 

Downstream Products

• 56-45-1 L-serin 
• 144-62-7 oxalic acid 
• 15996-22-2 3,6-dimethylidenepiperazine-2,5-dione 

Relevant articles and documents

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.