6,7-Dichloroquinoline-5,8-dione

Base Information

• Chemical Name: 6,7-Dichloroquinoline-5,8-dione
• CAS No.: 6541-19-1
• Molecular Formula: C9H3Cl2NO2
• Molecular Weight: 228.034
• Hs Code.: 2933499090
• NSC Number: 81047
• DSSTox Substance ID: DTXSID50215723
• Nikkaji Number: J849.785K
• Wikidata: Q83091788
• ChEMBL ID: CHEMBL132160
• Mol file: 6541-19-1.mol

Synonyms:6,7-dichloroquinoline-5,8-dione;6,7-DQDO

Chemical Property of 6,7-Dichloroquinoline-5,8-dione

Chemical Property:

• Vapor Pressure: 0.00016mmHg at 25°C
• Melting Point: 220-222 °C
• Refractive Index: 1.639
• Boiling Point: 331.1 °C at 760 mmHg
• PKA: -3.44±0.20(Predicted)
• Flash Point: 154 °C
• PSA: 47.03000
• Density: 1.63 g/cm³
• LogP: 2.14980
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 226.9540837
• Heavy Atom Count: 14
• Complexity: 338

Purity/Quality:

99% ^*data from raw suppliers

6,?7-?Dichloroquinoline-?5,?8-?dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=O)C(=C(C2=O)Cl)Cl)N=C1
• Recent ClinicalTrials: Efficacy and Safety of DA-3002 in Short Children Borns SGA.
• Uses: 6,?7-?Dichloroquinoline-?5,?8-?dione is a reagent used in the synthesis of pharmaceuticals, such as a platinum(II) complex with antitumor activity.

Technology Process of 6,7-Dichloroquinoline-5,8-dione

There total 11 articles about 6,7-Dichloroquinoline-5,8-dione 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: 90.0%

5-amino-8-hydroxyquinoline sulfate → 6,7-dichloroquinoline-5,8-dione (6541-19-1)

Guidance literature:

With hydrogenchloride; potassium chlorate; In water; at 60 ℃; for 0.5h;

DOI:10.1016/j.jinorgbio.2019.110701

Reference yield: 90.0%

5-amino-8-hydroxyquinoline dihydrochloride (21302-43-2) → 6,7-dichloroquinoline-5,8-dione (6541-19-1)

Guidance literature:

With hydrogenchloride; sodium chlorate; at 50 - 60 ℃; for 0.5h;

Reference yield: 65.0%

8-quinolinol (148-24-3,24804-14-6) → 6,7-dichloroquinoline-5,8-dione (6541-19-1)

Guidance literature:

With hydrogenchloride; sodium perchlorate; sodium hydroxide; at 80 ℃; for 3h;

DOI:10.1039/c5ra11127g

upstream raw materials:

8-quinolinol

5-amino-8-hydroxyquinoline dihydrochloride

5-Nitroso-8-hydroxyquinoline hydrochloride

5-amino-8-hydroxyquinoline

Downstream raw materials:

7-chloro-6-(dimethylamino)-5,8-quinolinedione

6-amino-7-chloro-5,8-quinolinequinone

6-chloro-7-((2-morpholin-4-yl)ethylamino)quinoline-5,8-dione

Refernces

• 1、 Modranka, Jakub,Drogosz-Stachowicz, Joanna,Pietrzak, Anna,Janecka, Anna,Janecki, Tomasz. "Synthesis and structure–activity relationship study of novel 3-diethoxyphosphorylfuroquinoline-4,9-diones with potent antitumor efficacy". . . Retrieved 2021.
• 2、 Meng, Ting,Qin, Qi-Pin,Chen, Zi-Lu,Zou, Hua-Hong,Wang, Kai,Liang, Fu-Pei. "Discovery of high in vitro and in vivo antitumor activities of organometallic ruthenium(ii)-arene complexes with 5,7-dihalogenated-2-methyl-8-quinolinol". . p. 5352 - 5360. Retrieved 2019.
• 3、 Yang, Yan,Bin, Yi-Dong,Qin, Qi-Pin,Luo, Xu-Jian,Zou, Bi-Qun,Zhang, Hua-Xin. "Novel Quinoline-based Ir(III) Complexes Exhibit High Antitumor Activity in Vitro and in Vivo". . p. 1614 - 1619. Retrieved 2019.
• 4、 Ding, Yang,Wu, Qiong,Zheng, Kangdi,An, Linkun,Hu, Xiaoying,Mei, Wenjie. "Imaging of the nuclei of living tumor cells by novel ruthenium(II) complexes coordinated with 6-chloro-5-hydroxylpyrido[3,2-a]phenazine". . p. 63330 - 63337. Retrieved 2015.
• 5、 Ciftci, Halil I.,Bayrak, Nilüfer,Y?ld?z, Mahmut,Y?ld?r?m, Hatice,Sever, Belgin,Tateishi, Hiroshi,Otsuka, Masami,Fujita, Mikako,Tuyun, Ama? Fatih. "Design, synthesis and investigation of the mechanism of action underlying anti-leukemic effects of the quinolinequinones as LY83583 analogs". . . Retrieved 2021/07/21.