3-BROMOQUINOLIN-5-OL

Base Information

• Chemical Name: 3-BROMOQUINOLIN-5-OL
• CAS No.: 1123738-15-7
• Molecular Formula: C₉H₆BrNO
• Molecular Weight: 224.057
• Mol file: 1123738-15-7.mol

Synonyms:3-bromo-5-hydroxyquinoline

Chemical Property of 3-BROMOQUINOLIN-5-OL

Chemical Property:

• Boiling Point: 348.4±22.0 °C(Predicted)
• PKA: 8.07±0.40(Predicted)
• Density: 1.705±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C

Purity/Quality:

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

3-Bromoquinolin-5-ol >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-BROMOQUINOLIN-5-OL

There total 3 articles about 3-BROMOQUINOLIN-5-OL 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: 84.0%

3-bromoquinolin-5-amine (116632-57-6) → 3-bromo-5-hydroxyquinoline (1123738-15-7)

Guidance literature:

With sulfuric acid; sodium nitrite; In water; at 0 - 100 ℃;

DOI:10.1021/acs.joc.5b01119

Reference yield: 30.0%

3-bromo-5-nitroquinoline (116632-33-8) → 3-bromo-5-hydroxyquinoline (1123738-15-7)

Guidance literature:

3-bromo-5-nitroquinoline; With iron; acetic acid; Reflux;

With sulfuric acid; acetic acid; sodium nitrite; In water; at 0 ℃;

With sulfuric acid; water; Reflux;

DOI:10.1021/jm101340q

Reference yield:

5-nitroquinoline (607-34-1) → 3-bromo-5-hydroxyquinoline (1123738-15-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-Bromosuccinimide; acetic acid / Reflux

2.1: iron(III) chloride; iron; acetic acid / ethanol / Reflux

3.1: sulfuric acid; acetic acid; sodium nitrite / water / 0 °C

3.2: Reflux

With iron(III) chloride; N-Bromosuccinimide; sulfuric acid; iron; acetic acid; sodium nitrite; In ethanol; water; 3.2: Sandmeyer reaction;

DOI:10.1016/j.bmcl.2008.11.062

upstream raw materials:

3-bromoquinolin-5-amine

5-nitroquinoline

3-bromo-5-nitroquinoline

Downstream raw materials:

5-(3-nitrobenzyloxy)-3-(4-methylpiperazin-1-yl)quinoline

C₁₆H₁₁BrN₂O₃

Refernces

• 1、 Wang, Yuanxiang,Ai, Jing,Wang, Ying,Chen, Yi,Wang, Lu,Liu, Gang,Geng, Meiyu,Zhang, Ao. "Synthesis and c-met kinase inhibition of 3,5-disubstituted and 3,5,7-trisubstituted quinolines: Identification of 3-(4-acetylpiperazin-1-yl)-5- (3-nitrobenzylamino)-7- (trifluoromethyl)quinoline as a novel anticancer agent". scheme or table. p. 2127 - 2142. Retrieved 2011/06/17.