2,5-Piperazinedione

Base Information

• Chemical Name: 2,5-Piperazinedione
• CAS No.: 106-57-0
• Molecular Formula: C4H6N2O2
• Molecular Weight: 114.104
• Hs Code.: 29335990
• European Community (EC) Number: 203-411-5
• NSC Number: 26345
• UNII: 240L69DTV7
• DSSTox Substance ID: DTXSID8059342
• Nikkaji Number: J4.036C
• Wikipedia: 2,5-Diketopiperazine
• Wikidata: Q27101960
• Metabolomics Workbench ID: 49838
• ChEMBL ID: CHEMBL125229
• Mol file: 106-57-0.mol

Synonyms:2,5-diketopiperazine;2,5-dioxopiperazine;cyclo(Gly-Gly);cyclo(glycylglycyl)

Chemical Property of 2,5-Piperazinedione

Chemical Property:

• Appearance/Colour: white to slightly yellow crystalline powder
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.467
• Boiling Point: 573.65 °C at 760 mmHg
• PKA: 12.88±0.20(Predicted)
• Flash Point: 301.886 °C
• PSA: 58.20000
• Density: 1.247 g/cm³
• LogP: -1.11000
• Storage Temp.: Store below +30°C.
• Solubility.: 142g/l
• Water Solubility.: Soluble in water (142mg/L).
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 114.042927438
• Heavy Atom Count: 8
• Complexity: 116

Purity/Quality:

GlycineAnhydride(2,5-Piperazinedione) ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: C1C(=O)NCC(=O)N1
• Uses: 2,5-Piperazinedione, can be used as an intermediate in the preparation of various pharmaceutical and biologically active compounds. It can be used in the synthesis of dipeptide isosteres by cross-metathesis.

Technology Process of 2,5-Piperazinedione

There total 130 articles about 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: 16.1%

N,N'-diacetylpiperazin-2,5-dione (3027-05-2) + tert-butylamine (75-64-9) → Glycine anhydride (106-57-0) + 1-acetyl-2,5-piperazinedione (59595-18-5) + N-tert-butylacetamide (762-84-5)

Guidance literature:

In acetonitrile; at 0 ℃; for 60h; Product distribution; Irradiation; reaction in dark and without t-butylamine; var. solvents;

DOI:10.3987/COM-92-6265

Reference yield: 7.2%

N,N'-diacetylpiperazin-2,5-dione (3027-05-2) → Glycine anhydride (106-57-0) + 1-acetyl-2,5-piperazinedione (59595-18-5) + N-tert-butylacetamide (762-84-5)

Guidance literature:

With tert-butylamine; In acetonitrile; at 0 ℃; for 60h; Irradiation;

DOI:10.3987/COM-92-6265

Reference yield:

[(S)-2-(2-{(S)-2-[2-((S)-2-Amino-3-phenyl-propionylamino)-acetylamino]-4-methyl-pentanoylamino}-acetylamino)-3-methyl-butyrylamino]-acetic acid (85864-65-9) → Glycine anhydride (106-57-0) + N-DL-valyl-glycine (14297-28-0,6491-60-7) + DL-Leucyl-glycin (615-82-7) + phenylalanylglycine (4294-26-2) + 3-isopropyl-piperazine-2,5-dione (16944-60-8) + 3-benzyl-piperazine-2,5-dione (10125-07-2)

Guidance literature:

In water; at 100 ℃; Product distribution; Mechanism; pH_7.26;

DOI:10.1021/jo00161a036

upstream raw materials:

phthalic anhydride

3,6-bis-benzyloxy-2,5-dihydro-pyrazine

2-{2-[2-(2-chloroacetamido)acetamido]acetamido}acetic acid

glycine isopropyl ester

Downstream raw materials:

N,N'-dibenzoylpiperazine-2,5-dione

1,4-di(hydroxymethyl)-2,5-diketopiperazine

N-[N-(α-bromo-isovaleryl)-glycyl]-glycine

2-[(3-methylbutyl)amino]ethanol

Refernces

• 1、 Al-Subu,Jondi,Amer,Hannoun,Musmar. "Osmium(VIII)-catalyzed oxidation of some cyclic amines by potassium hexacyanoferrate(III) in alkaline media: A kinetics and mechanistic study". . p. 478 - 484. Retrieved 2003.
• 2、 Itoh, Kuniaki,Sera, Akira. "Addition reaction of 1,4-Dibromo-2,5-piperazinedione with 3,4-dihydro-2H-pyran". . p. 479 - 482. Retrieved 1986.
• 3、 Buckingham et al.. "-". . p. 5571,5574. Retrieved 1970.
• 4、 Blake, Timothy R.,Ho, Wilson C.,Huttner, Melanie A.,Turlington, Christopher R.,Waymouth, Robert M.,Wender, Paul A.,Zang, Xiaoyu. "Synthesis and mechanistic investigations of pH-responsive cationic poly(aminoester)s". . p. 2951 - 2966. Retrieved 2020.
• 5、 Smith, Aaron J.,Ali, Farukh I.,Soldatov, Dmitriy V.. "Glycine homopeptides: The effect of the chain length on the crystal structure and solid state reactivity". . p. 7196 - 7208. Retrieved 2014.
• 6、 Li, Jun,Brill, Thomas B.. "Spectroscopy of hydrothermal reactions. 27. Simultaneous determination of hydrolysis rate constants of glycylglycine to glycine and glycylglycine-diketopiperazine equilibrium constants at 310-330°C and 275 bar". . p. 8575 - 8577. Retrieved 2003.
• 7、 Ly, Hong Giang T.,Absillis, Gregory,Parac-Vogt, Tatjana N.. "Comparative study of the reactivity of zirconium(IV)-substituted polyoxometalates towards the hydrolysis of oligopeptides". . p. 2206 - 2215. Retrieved 2015.
• 8、 Nonappa,Ahonen, Kari,Lahtinen, Manu,Kolehmainen, Erkki. "Cyclic dipeptides: Catalyst/promoter-free, rapid and environmentally benign cyclization of free amino acids". . p. 1203 - 1209. Retrieved 2011.
• 9、 Joshi,Verma, Sandeep. "Participation of aromatic side chains in diketopiperazine ensembles". . p. 4231 - 4234. Retrieved 2008.
• 10、 Sofokleous, Panagiotis,Stride, Eleanor,Edirisinghe, Mohan. "Preparation, characterization, and release of amoxicillin from electrospun fibrous wound dressing patches". . p. 1926 - 1938. Retrieved 2013.