5-Bromo-2-nitropyridin-3-OL

Base Information

• Chemical Name: 5-Bromo-2-nitropyridin-3-OL
• CAS No.: 691872-15-8
• Molecular Formula: C5H3BrN2O3
• Molecular Weight: 218.994
• DSSTox Substance ID: DTXSID30697422
• Wikidata: Q82627318
• Mol file: 691872-15-8.mol

Synonyms:5-BROMO-2-NITROPYRIDIN-3-OL;691872-15-8;5-Bromo-2-nitro-pyridin-3-ol;5-Bromo-2-nitro-3-Pyridinol;5-Bromo-3-hydroxy-2-nitropyridine;MFCD15527395;SCHEMBL2586421;DTXSID30697422;OOPJQYJTWRBGME-UHFFFAOYSA-N;5-bromo-3-hydroxyl-2-nitropyridine;5-bromo-3-hydroxy-2-nitro-pyridine;AKOS015994833;SB38346;AS-59322;SY127411;CS-0060276;FT-0763982;F13805;J-516984

Chemical Property of 5-Bromo-2-nitropyridin-3-OL

Chemical Property:

• Boiling Point: 393.4±37.0 °C(Predicted)
• PKA: -1.63±0.10(Predicted)
• PSA: 78.94000
• Density: 2.006±0.06 g/cm3(Predicted)
• LogP: 1.98110
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 217.93270
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

5-Bromo-3-hydroxy-2-nitropyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=NC(=C1O)[N+](=O)[O-])Br
• Uses: 5-Bromo-3-hydroxy-2-nitropyridine was used to design potent and selective inhibitors to overcome clinical anaplastic Lymphoma kinase mutations resistant to Crizotinib (C785000), a potential antitumor agent.

Technology Process of 5-Bromo-2-nitropyridin-3-OL

There total 1 articles about 5-Bromo-2-nitropyridin-3-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: 90.0%

5-bromopyridine-3-ol (74115-13-2) → 5-bromo-3-hydroxy-2-nitropyridine (691872-15-8)

Guidance literature:

With sulfuric acid; nitric acid; for 20h; Cooling with ice;

Reference yield: 93.5%

5-bromo-3-hydroxy-2-nitropyridine (691872-15-8) + p-methoxybenzyl chloride (824-94-2) → C13H11BrN2O4

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 14h;

Reference yield: 89.5%

5-bromo-3-hydroxy-2-nitropyridine (691872-15-8) + (RS)-1-(2-chloro-5-fluorophenyl)ethanol (700-31-2) → 5-bromo-3-(1-(2-chloro-5-fluorophenyl)ethoxy)-2-nitropyridine

Guidance literature:

5-bromo-3-hydroxy-2-nitropyridine; (RS)-1-(2-chloro-5-fluorophenyl)ethanol; With triphenylphosphine; In tetrahydrofuran; for 0.5h; Cooling with ice;

With di-isopropyl azodicarboxylate; at 0 - 20 ℃; for 4h;

DOI:10.1016/j.bmcl.2019.04.011

upstream raw materials:

5-bromopyridine-3-ol

Downstream raw materials:

(±)-5-bromo-3-(1-(2,6-dichloro-3-fluoropheny)ethoxy)pyridin-2-amine

(R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine

(R)-3-[1-(2,5-difluorophenyl)ethoxy]-5-(3-methyl-1H-pyrazol-4-yl)pyridin-2-amine

2-[(1R)-1-{[2-amino-5-(3-methyl-1H-pyrazol-4-yl)-pyridin-3-yl]oxy}ethyl]-4-fluorobenzonitrile

Refernces

• 1、 -. "SELECTIVE JAK2 INHIBITOR AND APPLICATION THEREOF". Paragraph 0076; 0078; 0079; 0137-0139; 0157. . Retrieved 2021/02/25.
• 2、 -. "HPK1 INHIBITORS, PREPARATION METHOD AND APPLICATION THEREOF". Page/Page column 85. . Retrieved 2019/11/12.