2,3-Dihydroxyquinoxaline

Base Information

• Chemical Name: 2,3-Dihydroxyquinoxaline
• CAS No.: 15804-19-0
• Deprecated CAS: 6287-20-3
• Molecular Formula: C8H6 N2 O2
• Molecular Weight: 162.148
• Hs Code.: 29339900
• European Community (EC) Number: 239-901-0
• NSC Number: 9431,8698
• UNII: APO55IZ9E1
• DSSTox Substance ID: DTXSID9065946
• Nikkaji Number: J48.373G
• Wikidata: Q21099569
• ChEMBL ID: CHEMBL282672
• Mol file: 15804-19-0.mol

Synonyms:2,3-dihydroxyquinoxaline

Chemical Property of 2,3-Dihydroxyquinoxaline

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.762
• Boiling Point: 470.9°Cat760mmHg
• PKA: 10.66±0.20(Predicted)
• Flash Point: 238.6°C
• PSA: 65.72000
• Density: 1.336g/cm³
• LogP: 0.21640
• Storage Temp.: 2-8°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 162.042927438
• Heavy Atom Count: 12
• Complexity: 203

Purity/Quality:

98%, ^*data from raw suppliers

1,4-Dihydroquinoxaline-2,3-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 22-24/25-39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Rings
• Canonical SMILES: C1=CC=C2C(=C1)NC(=O)C(=O)N2

Technology Process of 2,3-Dihydroxyquinoxaline

There total 74 articles about 2,3-Dihydroxyquinoxaline 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: 100.0%

oxalic acid (144-62-7,97993-78-7) + 1,2-diamino-benzene (95-54-5) → quinoxaline-2,3-dione (15804-19-0,6287-20-3)

Guidance literature:

at 150 ℃; for 8h; Further Variations:; Temperatures; Product distribution; solid-state reaction;

DOI:10.1002/1099-0690(200204)2002:8<1368::AID-EJOC1368>3.0.CO;2-6

Reference yield: 93.0%

ethyl (2E)-(3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidene)ethanoate (30681-63-1,86482-20-4) → quinoxaline-2,3-dione (15804-19-0,6287-20-3)

Guidance literature:

With peracetic acid; In water; at 50 ℃; for 8h;

Reference yield: 91.0%

quinoxalin-2(1)-one (1196-57-2) → quinoxaline-2,3-dione (15804-19-0,6287-20-3)

Guidance literature:

With ammonium peroxydisulfate; In water; acetonitrile; at 60 ℃;

upstream raw materials:

2,3-diethynylquinoxaline

quinoxalin-2⁽¹⁾-one

2-(methylthio)quinoxaline

2-mercapto-3-hydrazinoquinoxaline

Downstream raw materials:

3-(piperazin-1-yl)quinoxalin-2(1H)-one

6-chloroquinoxaline-2,3(1H,4H)-dione

6-nitro-1,2,3,4-tetrahydroquinoxaline-2,3-dione

2,2,2-trifluoro-N-[3-(3-methoxy-phenylethynyl)-quinoxalin-2-yl]-acetamide

Refernces

• 1、 Kaupp, Gerd,Naimi-Jamal, M. Reza. "Quantitative cascade condensations between o-phenylenediamines and 1,2-dicarbonyl compounds without production of wastes". . p. 1368 - 1373. Retrieved 2002.
• 2、 Lewis, Tina R.,Smith, Jesse,Griffin, Kallie,Aguiar, Stephanie,Rueb, Kristen F.,Holmberg-Douglas, Natalie,Sampson, Ellen M.,Tomasetti, Skylar,Rodriguez, Sofia,Stachura, David L.,Arpin, Carolynn C.. "NHD2-15, a novel antagonist of Growth Factor Receptor-Bound Protein-2 (GRB2), inhibits leukemic proliferation". . . Retrieved 2020.
• 3、 Madrzak-Litwa, Iwona,Borowiak-Resterna, Aleksandra. "The use of diethylene glycol in the synthesis of 2,2'-bibenzimidazole from o-phenylenediamine and oxalic acid". . p. 177 - 180. Retrieved 2014.
• 4、 Sukanya, Panaganti,Reddy, Chittireddy Venkata Ramana. "Structural investigation, DNA interactions and in?vitro anticancer studies of transition metal complexes of 3-(2-(2, 4-dihydroxy benzylidene) hydrazinyl) quinoxalin-2(1H) -one". . . Retrieved 2021.
• 5、 Alsaif, Nawaf A.,Taghour, Mohammed S.,Alanazi, Mohammed M.,Obaidullah, Ahmad J.,Alanazi, Wael A.,Alasmari, Abdullah,Albassam, Hussam,Dahab, Mohammed A.,Mahdy, Hazem A.. "Identification of new [1,2,4]triazolo[4,3-a]quinoxalines as potent VEGFR-2 tyrosine kinase inhibitors: Design, synthesis, anticancer evaluation, and in silico studies". . . Retrieved 2021.
• 6、 Jubie, Selvaraj,Gayathri, Rajamanickam,Srividya, Ammayappan Byung,Kalirajan, Rajagopal,Prabitha, Prabakaran,Sankar, Sundaram,Elango, Kannan. "Synthesis and characterization of some novel quinoxaline-2, 3-dione derivatives: A preliminary investigation on their activity against a human epithelial carcinoma cell line". . p. 317 - 320. Retrieved 2011.
• 7、 Sukanya, Panaganti,Venkata Ramana Reddy, Chittireddy. "Synthesis, characterization and in vitro anticancer, DNA binding and cleavage studies of Mn (II), Co (II), Ni (II) and Cu (II) complexes of Schiff base ligand 3-(2-(1-(1H-benzimidazol-2-yl)ethylidene)hydrazinyl)quinoxalin-2(1H)-one and crystal structure of the ligand". . . Retrieved 2018.
• 8、 Adil, A. Gobouri. "Synthesis and Biological Evaluation of Some N-Substituted Quinoxaline Derivatives as Antitumor Agents". . p. 409 - 416. Retrieved 2020.
• 9、 Dewangan, Dhansay,Nakhate, Kartik,Mishra, Achal,Thakur, Alok Singh,Rajak, Harish,Dwivedi, Jaya,Sharma, Swapnil,Paliwal, Sarvesh. "Design, Synthesis, and Characterization of Quinoxaline Derivatives as a Potent Antimicrobial Agent". . p. 566 - 578. Retrieved 2019.
• 10、 Jian, Fang-Fang,Zhao, Pu-Su. "Experimental and ab initio calculational studies on 2,3-diketo- benzopiperazine". . p. 133 - 139. Retrieved 2004.