Quindoxin

Base Information

• Chemical Name: Quindoxin
• CAS No.: 2423-66-7
• Molecular Formula: C8H6 N2 O2
• Molecular Weight: 162.148
• Hs Code.: 2933990090
• European Community (EC) Number: 219-352-3
• NSC Number: 193508,21653
• UNII: AMX8J6YS1H
• DSSTox Substance ID: DTXSID8046165
• Nikkaji Number: J7.886G
• Wikidata: Q27274014
• NCI Thesaurus Code: C72588
• Metabolomics Workbench ID: 45789
• ChEMBL ID: CHEMBL2104626
• Mol file: 2423-66-7.mol

Synonyms:1,4-dihydroxyquinoxaline;Grofas;ICI 8173;quindoxin;quindoxin hydride;quindoxin ion (1+);quindoxin ion (1-);quinoxaline 1,4-di-N-oxide;quinoxaline 1,4-dioxide;quinoxaline-di-N-oxide

Chemical Property of Quindoxin

Chemical Property:

• Melting Point: 242°C
• Refractive Index: 1.5770 (estimate)
• Boiling Point: °Cat760mmHg
• PKA: 2.67±0.10(Predicted)
• Flash Point: °C
• PSA: 50.92000
• Density: g/cm³
• LogP: 1.69680
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 162.042927438
• Heavy Atom Count: 12
• Complexity: 206

Purity/Quality:

99% ^*data from raw suppliers

QUINDOXIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)N(C=C[N+]2=O)[O-]
• Uses: Quindoxin is a potential anti-bacterial agent with a wide range biological properties. Also, it potentially display anti-malarial, anti-leishmanial and anti-tuberculosis activity. Potent anti-mycobacterium tuberculosis agent.

Technology Process of Quindoxin

There total 16 articles about Quindoxin 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: 99.0%

2,3-diethynylquinoxaline (91-19-0) → quinoxaline 1,4-di-N-oxide (2423-66-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 0 - 20 ℃; for 48h; Inert atmosphere;

DOI:10.1016/j.tet.2017.02.014

Reference yield: 82.0%

Quinoxaline-2-carboxaldehyde-1,4-dioxide hydrate (76286-62-9) → quinoxaline 1,4-di-N-oxide (2423-66-7) + Quinoxaline-3-carboxylic Acid 1-Oxide (22875-69-0)

Guidance literature:

With sodium hydrogencarbonate; at 22 ℃; for 144h;

DOI:10.1007/BF00513172

Reference yield: 79.0%

vinyl acetate (108-05-4,9003-20-7) + benzofurazan oxide (480-96-6,68100-26-5) → quinoxaline 1,4-di-N-oxide (2423-66-7)

Guidance literature:

With diethylamine; In ethyl acetate; 1.) 0 deg C, 3 h, 2.) RT, 72 h;

DOI:10.1021/jm00022a014

upstream raw materials:

2,3-diethynylquinoxaline

peracetic acid

acetic acid

benzofurazan oxide

Downstream raw materials:

quinoxaline-2,3-dione

1-acetoxy-2(1H)-quinoxalinone

1-hydroxy-2(1H)-quinoxalinone

quinoxaline-N-oxide

Refernces

• 1、 Zhang, Huichun,Huang, Ching-Hua. "Reactivity and transformation of antibacterial N-oxides in the presence of manganese oxide". . p. 593 - 601. Retrieved 2005.
• 2、 Biswas, Aniruddha,Karmakar, Ujjwal,Nandi, Shiny,Samanta, Rajarshi. "Copper-Catalyzed Direct, Regioselective Arylamination of N-Oxides: Studies to Access Conjugated π-Systems". . p. 8933 - 8942. Retrieved 2017/09/11.
• 3、 Carmeli, Mira,Rozen, Shlomo. "A new efficient route for the formation of quinoxaline N-oxides and N,N′-dioxides using HOF·CH3CN". . p. 5761 - 5765. Retrieved 2007/10/03.