49715-78-8

Basic information

• Product Name: piperazine-2,3,5,6-tetrone
• Synonyms: piperazine-2,3,5,6-tetrone
• CAS NO: 49715-78-8
• Molecular Formula: C₄H₂N₂O₄
• Molecular Weight: 142.06968
• Mol File: 49715-78-8.mol

Chemical Properties

• Appearance: /
• Density: 1.681g/cm³
• Refractive Index: 1.519
• PKA: 4.27±0.20(Predicted)
• CAS DataBase Reference: piperazine-2,3,5,6-tetrone(CAS DataBase Reference)
• NIST Chemistry Reference: piperazine-2,3,5,6-tetrone(49715-78-8)
• EPA Substance Registry System: piperazine-2,3,5,6-tetrone(49715-78-8)

Safety Data

• Hazardous Substances Data: 49715-78-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Piperazine-2,3,5,6-tetrone is used as a precursor in the synthesis of pharmaceutical compounds due to its versatile chemical structure and potential antitumor and anticancer properties. Its ability to participate in Diels-Alder reactions further enhances its utility in the development of novel therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, piperazine-2,3,5,6-tetrone is utilized as a key building block for the preparation of a wide range of organic compounds. Its unique structure and reactivity make it a valuable component in the synthesis of complex organic molecules.
Used in Material Science:
Piperazine-2,3,5,6-tetrone is employed in the development of novel materials due to its potential to form stable complexes and contribute to the creation of new material properties. Its versatility in chemical reactions allows for the exploration of its use in various material applications, such as in the development of advanced polymers or other functional materials.
Used in Research and Development:
Piperazine-2,3,5,6-tetrone is used as a research compound in academic and industrial laboratories to explore its chemical properties, reactivity, and potential applications. Its unique structure and potential as a precursor for various compounds make it an interesting subject for further investigation and development.

InChI:InChI=1/C4H2N2O4/c7-1-2(8)6-4(10)3(9)5-1/h(H,5,7,9)(H,6,8,10)

Upstream product

• 471-47-6 oxamic acid 
• 617-36-7 Ethyl oxamate 
• 100-61-8 N-methylaniline 
• 2213-63-0 2,3-dichloroquinoxaline 
• 15804-19-0 2,3-dihydroxyquinoxaline 
• 106-57-0 Glycine anhydride 
• 23409-30-5 cyclo(-L-Ser-L-Ser-) 
• 10026-13-8 phosphorus pentachloride 
• 10025-87-3 trichlorophosphate 

Downstream Products

• 7670-72-6 3,6-dianilino-pyrazine-2,5-dione 
• 471-46-5 Oxalamide 
• 144-62-7 oxalic acid 

Relevant articles and documents

Protein backbone modification by novel C(α)-C side-chain scission

α-Ketoamide (-NH-CO-CO-) units in intact peptides are generated from Ser/Thr residues via Ru(VIII)-catalyzed C(α)-C side-chain scission. Facets associated with this novel α-carbon modification have been probed with 75 peptides chosen to represent every possible peptide environment. The reactions were carried out at room temperature with in situ generated Ru(VIII) in biphasic (CH3CN/CCl4/pH 3 phosphate buffer, 1:1:2 v/v) medium. Whereas Ser/Thr residues placed at the C-terminal end in peptides undergo N-C bond scission leading to des-Ser/Thr peptide amides - thus acting as Gly equivalents in simulating the α-amidating action of pituitary enzymes - those located at the N-terminal or nonterminal or even at the C-terminal position (protected as amide) were found to undergo oxidative C-C bond scission (involving C(α) and C side-chain bond), resulting in the generation of α-ketoamide (-NH-CO-CO-) units in the intact peptide backbone. The difference in the products arising from C(α)-C side-chain scission of Ser/Thr esters and amides is rationalized on the basis of a common mechanism involving either oxaloesters [PeP-NH-CO-COX; X = OMe] or oxalamides [X = NH2 or NH-Pep] arising from the oxidation of initially formed carbinolamide intermediates [Pep-NH-CH(OH)-COX], wherein, while the former are shown to undergo hydrolysis to terminal amides [Pep-NH2], the oxalamides are found to be stable to hydrolysis. Ancillary noteworthy findings are those of peptide bond scission when contiguous Ser-Ser/Thr-Thr residues are present and the oxidative cleavage at C-terminal Tyr/Trp sites generating des amides. The oxidative methodology presented here is mild, simple, and practical and proceeds with chiral retention. The insensitivity of a large number of amino acid residues, such as Gly, Ala, Leu, Asn, Gln, Asp, Glu, Pro, Arg, Phe, Lys, Val, and Aib, and N-protecting groups, such as Boc, Z, and Bz, toward Ru(VIII) under the experimental conditions should make this methodology practical and useful. Sulfur-containing amino acids Cys and Met get oxidized to sulfones in the products.

ESR-Untersuchungen an Thioamiden, 8. Radikalanionen der Imidazolidintrione, Piperazindione, Piperazintetraone und Chinoxalindione sowie ihrer Schwefel-Analoga.

Cyclische Oxamid-Derivate vom Typ des Imidazolidin-4,5-dions, Piperazin-2,3-dions, Piperazin-2,3,5,6-tetraons und Chinoxalin-2,3-dions sowie Thio-Analoga und mit 2H, 13C oder 15N markierte Vertreter werden dargestellt und durch in-situ-Elektroreduktion in die entsprechenden Radikalanionen uebergefuehrt.Aus deren isotropen und anisotropen ESR-Spektren sowie einer Analyse der Linienbreite und Linienform wird die Spindichteverteilung ermittelt und anhand MO-theoretisch berechneter Werte diskutiert.