Parabanic acid

Base Information

• Chemical Name: Parabanic acid
• CAS No.: 120-89-8
• Molecular Formula: C3H2N2O3
• Molecular Weight: 114.06
• Hs Code.: 2933990090
• European Community (EC) Number: 204-434-3
• NSC Number: 9789
• UNII: 3XGR439T9P
• DSSTox Substance ID: DTXSID2059516
• Nikkaji Number: J9.351C
• Wikidata: Q17190867
• Metabolomics Workbench ID: 67821
• ChEMBL ID: CHEMBL1534940
• Mol file: 120-89-8.mol

Synonyms:parabanic acid

Chemical Property of Parabanic acid

Chemical Property:

• Appearance/Colour: white crystalline solid
• Melting Point: 249 °C (dec.)(lit.)
• Refractive Index: 1.507
• Boiling Point: 213.51°C (rough estimate)
• PKA: pK1:6.1 (25°C)
• PSA: 75.27000
• Density: 1.623 g/cm³
• LogP: -0.99000
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly, Heated)
• Water Solubility.: almost transparency
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 114.00654193
• Heavy Atom Count: 8
• Complexity: 155

Purity/Quality:

98%,99%, ^*data from raw suppliers

Parabanic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1(=O)C(=O)NC(=O)N1
• Uses: Parabanic acid appears to be an important marker of free radical reactions in vivo and may be used to monitor free radical activity and to evaluate pharmacological therapy with radical scavengers. Reactant for:? ;Enantiospecific assembly of homochiral, hexanuclear palladium complexes1? ;Mitsunobu reactions2? ;Quantitative cascade condensation reactions3Reactant for synthesis of:? ;Pyridine derivatives4? ;Nitroesters5? ;Parabanic acid derivatives6 A useful synthetic intermediate

Technology Process of Parabanic acid

There total 94 articles about Parabanic acid 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: 75.0%

uric Acid (69-93-2) → parabanic acid (120-89-8) + Oxalyldiurea (5676-27-7) + dehydro-allantoin (105245-87-2) + Allantoin (97-59-6)

Guidance literature:

With lithium hydroxide; iodine; In water; for 0.0833333h; excess of I₂;

DOI:10.1016/S0040-4020(01)87480-9

Reference yield:

uric Acid (69-93-2) → parabanic acid (120-89-8) + oxaluric acid (585-05-7) + Allantoin (97-59-6)

Guidance literature:

In water; for 2h; UV-irradiation;

DOI:10.1021/acs.joc.9b00163

Reference yield:

5-bromouracil (51-20-7) → parabanic acid (120-89-8) + 5,6-dihydroxypyrimidine-2,4(1H,3H)-dione (102636-37-3) + 5-bromobarbituric acid (19645-78-4) + 5,5-dihydroxy-pyrimidine-2,4,6-trione (3237-50-1) + oxaluric acid (585-05-7)

Guidance literature:

With sonolysis; In water; at 25 ℃; for 1.33333h; Product distribution; Mechanism;

upstream raw materials:

carbamoylimino-acetic acid

bis(phenyl) carbonate

Oxalamide

2,4-imidazolidinedione

Downstream raw materials:

6-methylquinoxaline-2,3-dione

oxamidobiuret

imidazolidone

2,4-imidazolidinedione

Refernces

• 1、 Yang, De-Li,Li, Jia-Rong,Lu, Hong-Yan,Zhang, Pan,Shi, Da-Xin. "A facile synthesis of imidazolidine-2,4,5-trione". . p. 625 - 626. Retrieved 2014.
• 2、 Poje, M.,Sokolic-Maravic, Lea. "THE MECHANISM FOR THE CONVERSION OF URIC ACID INTO ALLANTOIN AND DEHYDRO-ALLANTOIN. A NEW LOOK AT AN OLD PROBLEM". . p. 747 - 752. Retrieved 1986.
• 3、 Volk,Yost,Brajter-Toth. "On-line electrochemistry/thermospray/tandem mass spectrometry as a new approach to the study of redox reactions: the oxidation of uric acid.". . p. 1709 - 1717. Retrieved 1989.
• 4、 Matsui,Kamiya,Kawamura,Shibata,Muramatsu. "Ozonization of thio- and azauracils". . p. 2939 - 2941. Retrieved 1989.
• 5、 Bregnh?j, Mikkel,Dichmann, Lea,McLoughlin, Ciaran K.,Westberg, Michael,Ogilby, Peter R.. "Uric Acid: A Less-than-Perfect Probe for Singlet Oxygen". . p. 202 - 210. Retrieved 2019.
• 6、 Iida, Sayaka,Yamamoto, Yorihiro,Fujisawa, Akio. "(2,5-Dioxoimidazolidin-4-ylidene)aminocarbonylcarbamic Acid as a Precursor of Parabanic Acid, the Singlet Oxygen-Specific Oxidation Product of Uric Acid". . . Retrieved 2019.
• 7、 Mun?oz,Mvula,Braslavsky,Von Sonntag. "Singlet dioxygen formation in ozone reactions in aqueous solution". . p. 1109 - 1116. Retrieved 2001.
• 8、 Cazeneuve. "-". . p. 834. Retrieved 1899.
• 9、 Cai, Huaqiang,Shu, Yuanjie,Huang, Hui,Cheng, Bibo,Li, Jinshan. "Study on reactions of 2-(dinitromethylene)-4,5-imidazolidinedione". . p. 4369 - 4374. Retrieved 2004.
• 10、 Saladino, Raffaele,Botta, Giorgia,Bizzarri, Bruno Mattia,Di Mauro, Ernesto,Garcia Ruiz, Juan Manuel. "A Global Scale Scenario for Prebiotic Chemistry: Silica-Based Self-Assembled Mineral Structures and Formamide". . p. 2806 - 2811. Retrieved 2016/06/01.