3-Bromo-6-chloro-2-methoxypyridine

Base Information

• Chemical Name: 3-Bromo-6-chloro-2-methoxypyridine
• CAS No.: 1211526-62-3
• Molecular Formula: C₆H₅BrClNO
• Molecular Weight: 222.469
• Hs Code.: 2933399990
• DSSTox Substance ID: DTXSID70682493
• Wikidata: Q82606898
• Mol file: 1211526-62-3.mol

Synonyms:3-BROMO-6-CHLORO-2-METHOXYPYRIDINE;1211526-62-3;MFCD18257579;2-methoxy-3-bromo-6-chloropyridine;SCHEMBL15300740;DTXSID70682493;NPCVTFQTUUYXQP-UHFFFAOYSA-N;AKOS015892002;AM84278;SB21251;AC-27976;DS-17447;SY015982;FT-0702423;EN300-1914141;A857516

Chemical Property of 3-Bromo-6-chloro-2-methoxypyridine

Chemical Property:

• Boiling Point: 227.3±35.0 °C(Predicted)
• PKA: -1.99±0.10(Predicted)
• PSA: 22.12000
• Density: 1.650±0.06 g/cm3(Predicted)
• LogP: 2.50610
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 220.92430
• Heavy Atom Count: 10
• Complexity: 114

Purity/Quality:

99% ^*data from raw suppliers

3-Bromo-6-chloro-2-methoxypyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=N1)Cl)Br

Technology Process of 3-Bromo-6-chloro-2-methoxypyridine

There total 4 articles about 3-Bromo-6-chloro-2-methoxypyridine 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: 93.0%

3-bromo-2, 6-dichloropyridine (866755-20-6) + sodium methylate (124-41-4) → 3 -bromo-6-chloro-2-methoxypyridine (1211526-62-3)

Guidance literature:

With methanol; In acetonitrile;

DOI:10.1021/acs.oprd.8b00059

Reference yield: 92.67%

3-amino-6-chloro-2-methoxypyridine (914222-86-9) → 3 -bromo-6-chloro-2-methoxypyridine (1211526-62-3)

Guidance literature:

3-amino-6-chloro-2-methoxypyridine; With hydrogen bromide; sodium nitrite; In water; at 0 - 5 ℃; for 0.5h;

With copper(I) bromide; In water; at 20 ℃; for 2h;

Reference yield:

3-amino-2,6-dichloropyridine (62476-56-6) → 3 -bromo-6-chloro-2-methoxypyridine (1211526-62-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: methanol; tetrahydrofuran / 71.9 - 72.9 °C / Inert atmosphere; Large scale

2.1: hydrogen bromide / water / -10 °C / Large scale

2.2: 3 h / -6 - -1.5 °C / Large scale

2.3: 3.75 h / -10 °C / Large scale

With hydrogen bromide; In tetrahydrofuran; methanol; water;

upstream raw materials:

3-amino-2,6-dichloropyridine

2,6-dicholoro-3-nitropyridine

3-amino-6-chloro-2-methoxypyridine

3-bromo-2, 6-dichloropyridine

Downstream raw materials:

SiO₂

Refernces

• 1、 Smith, Aaron C.,Kung, Daniel W.,Shavnya, Andre,Brandt, Thomas A.,Dent, Philip D.,Genung, Nathan E.,Cabral, Shawn,Panteleev, Jane,Herr, Michael,Yip, Ka Ning,Aspnes, Gary E.,Conn, Edward L.,Dowling, Matthew S.,Edmonds, David J.,Edmonds, Ian D.,Fernando, Dilinie P.,Herrinton, Paul M.,Keene, Nandell F.,Lavergne, Sophie Y.,Li, Qifang,Polivkova, Jana,Rose, Colin R.,Thuma, Benjamin A.,Vetelino, Michael G.,Wang, Guoqiang,Weaver, John D.,Widlicka, Daniel W.,Price Wiglesworth, Kristin E.,Xiao, Jun,Zahn, Todd,Zhang, Yingxin. "Evolution of the Synthesis of AMPK Activators for the Treatment of Diabetic Nephropathy: From Three Preclinical Candidates to the Investigational New Drug PF-06409577". . p. 681 - 696. Retrieved 2018/05/23.