3-Bromo-5-iodopyridin-2-ol

Base Information

• Chemical Name: 3-Bromo-5-iodopyridin-2-ol
• CAS No.: 637348-81-3
• Molecular Formula: C5H3BrINO
• Molecular Weight: 299.89
• Hs Code.: 2933399990
• DSSTox Substance ID: DTXSID50698895
• Wikidata: Q82629458
• Mol file: 637348-81-3.mol

Synonyms:3-Bromo-5-iodopyridin-2-ol;637348-81-3;3-BROMO-2-HYDROXY-5-IODOPYRIDINE;3-Bromo-5-iodopyridin-2(1H)-one;3-BROMO-5-IODO-1H-PYRIDIN-2-ONE;SCHEMBL2374756;DTXSID50698895;GUCOEKKQKHACCX-UHFFFAOYSA-N;2-Hydroxy-3-bromo-5-iodopyridine;MFCD11044276;AKOS016002119;DS-14653;CS-0132117;FT-0739746;EN300-3181426;A868049;A1-03395;Z1269234992

Chemical Property of 3-Bromo-5-iodopyridin-2-ol

Chemical Property:

• Boiling Point: 308.0±42.0 °C(Predicted)
• PKA: 8.66±0.10(Predicted)
• PSA: 33.12000
• Density: 2.55±0.1 g/cm3(Predicted)
• LogP: 2.15430
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 298.84427
• Heavy Atom Count: 9
• Complexity: 209

Purity/Quality:

97% ^*data from raw suppliers

3-Bromo-2-hydroxy-5-iodopyridine 95.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=O)NC=C1I)Br

Technology Process of 3-Bromo-5-iodopyridin-2-ol

There total 2 articles about 3-Bromo-5-iodopyridin-2-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: 96.0%

3-bromo-pyridin-2-ol (13466-43-8) → 3-bromo-5-iodopyridin-2-ol (637348-81-3)

Guidance literature:

With N-iodo-succinimide; In acetonitrile; trifluoroacetic acid; at 20 ℃; for 15h;

Reference yield:

3,5-dibromo-2-hydroxypyridine (13472-81-6) → 3-bromo-5-iodopyridin-2-ol (637348-81-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: s-BuLi / -90 °C

1.2: 71 percent / H₂O / -90 °C

2.1: 92 percent / NIS / acetonitrile / 1 h / Heating

With N-iodo-succinimide; sec.-butyllithium; In acetonitrile;

DOI:10.1055/s-2003-41013

Reference yield:

3-bromo-5-iodopyridin-2-ol (637348-81-3) → (E)-4-(2-(5-bromo-6-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)pyridin-3-yl)vinyl)phenyl acetate (937183-69-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C

2: 77 percent / K₂CO₃; tetrabutylammonium bromide / Pd(OAc)2 / dimethylformamide / 2 h / 65 °C

With di-isopropyl azodicarboxylate; tetrabutylammomium bromide; potassium carbonate; triphenylphosphine; palladium diacetate; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Mitsunobu reaction / 2: Heck reaction;

DOI:10.1021/jm070025+

upstream raw materials:

3-bromo-pyridin-2-ol

3,5-dibromo-2-hydroxypyridine

Downstream raw materials:

(E)-(5-bromo-6-{2-[2-(2-fluoroethoxy)ethoxy]ethoxy}pyridin-3-yl)-2-(4-dimethylaminophenyl)-ethylene

(E)-(5-bromo-6-{2-[2-(2-fluoroethoxy)ethoxy]ethoxy}pyridin-3-yl)-2-(4-methylaminophenyl)-ethylene

tert-butyl (E)-4-(2-(5-bromo-6-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)pyridin-3-yl)vinyl)phenyl(methyl)carbamate

(E)-4-(2-(5-bromo-6-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)pyridin-3-yl)vinyl)phenyl acetate