4-Bromo-2-hydroxypyridine

Base Information

• Chemical Name: 4-Bromo-2-hydroxypyridine
• CAS No.: 36953-37-4
• Molecular Formula: C5H4BrNO
• Molecular Weight: 173.997
• Hs Code.: 29333990
• European Community (EC) Number: 640-429-6
• DSSTox Substance ID: DTXSID00355749
• Nikkaji Number: J3.479.549E
• Wikidata: Q72457002
• Mol file: 36953-37-4.mol

Synonyms:4-bromopyridone

Chemical Property of 4-Bromo-2-hydroxypyridine

Chemical Property:

• Vapor Pressure: 0.418mmHg at 25°C
• Melting Point: 186 °C
• Refractive Index: 1.543
• Boiling Point: 305.9 °C at 760 mmHg
• PKA: 10.54±0.10(Predicted)
• Flash Point: 138.8 °C
• PSA: 33.12000
• Density: 1.776 g/cm³
• LogP: 1.54970
• Storage Temp.: Room temperature.
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 172.94763
• Heavy Atom Count: 8
• Complexity: 171

Purity/Quality:

99% ^*data from raw suppliers

4-Bromo-2-hydroxypyridine ^*data from reagent suppliers

Safty Information:

• Statements: 36/38
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CNC(=O)C=C1Br
• Uses: 4-Bromo-2-hydroxypyridine is used as a reagent to synthesize trans-3,4’-bispyridinylethylenes, compounds that act as inhibitors of protein kinase B that are used to treat cancer.

Technology Process of 4-Bromo-2-hydroxypyridine

There total 6 articles about 4-Bromo-2-hydroxypyridine 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: 88.0%

4-bromo-2-methoxypyridine (100367-39-3) → 4-bromo-2(1H)-pyridinone (36953-37-4)

Guidance literature:

4-bromo-2-methoxypyridine; With hydrogenchloride; water; In 1,4-dioxane; at 50 - 90 ℃;

With sodium hydroxide; In 1,4-dioxane; water; pH=8 - 9;

Reference yield: 86.0%

2-chloro-4-bromopyridine (73583-37-6) → 4-bromo-2(1H)-pyridinone (36953-37-4)

Guidance literature:

2-chloro-4-bromopyridine; With potassium tert-butylate; In tert-Amyl alcohol; at 80 ℃; for 16h; Schlenk technique; Inert atmosphere;

With formic acid; at 20 ℃; for 24h;

DOI:10.1055/s-0034-1378703

Reference yield: 82.0%

2-(benzyloxy)-4-bromopyridine (960298-00-4) → 4-bromo-2(1H)-pyridinone (36953-37-4)

Guidance literature:

With hydrogenchloride; In methanol; Reflux;

DOI:10.1055/s-0035-1560469

upstream raw materials:

4-bromo-2-methoxypyridine

2-chloro-4-bromopyridine

2-(benzyloxy)pyridin-4-amine

2-(benzyloxy)-4-bromopyridine

Downstream raw materials:

4-bromo-1-(2-hydroxyethyl)pyridin-2(1H)-one

4-bromo-2-(difluoromethoxy)pyridine

C₁₄H₁₈BrNO₃

1-methyl-4-phenyl-2(1H)-pyridone

Refernces

• 1、 Chen, Wenteng,Guo, Xiao,Zhang, Can,Ke, Di,Zhang, Guolin,Yu, Yongping. "Discovery of 2-aminopyridines bearing a pyridone moiety as potent ALK inhibitors to overcome the crizotinib-resistant mutants". . . Retrieved 2019/10/02.
• 2、 Wysocki, Jedrzej,Schlepphorst, Christoph,Glorius, Frank. "Asymmetric Homogeneous Hydrogenation of 2-Pyridones". supporting information. p. 1557 - 1562. Retrieved 2015/06/30.