2-Bromo-3-chloro-5-hydroxypyridine

Base Information

• Chemical Name: 2-Bromo-3-chloro-5-hydroxypyridine
• CAS No.: 130284-56-9
• Molecular Formula: C₅H₃BrClNO
• Molecular Weight: 208.442
• Hs Code.: 2933399090
• European Community (EC) Number: 810-329-9
• DSSTox Substance ID: DTXSID40562011
• Nikkaji Number: J323.949G
• Wikidata: Q72453442
• Mol file: 130284-56-9.mol

Synonyms:2-Bromo-3-chloro-5-hydroxypyridine;130284-56-9;6-bromo-5-chloropyridin-3-ol;3-Pyridinol, 6-bromo-5-chloro-;6-bromo-5-chloro-3-pyridinol;MFCD09835244;SCHEMBL363346;DTXSID40562011;DHKTYYVUEJTFHF-UHFFFAOYSA-N;BCP22882;AKOS015835791;BCP9000093;CS-W018908;DS-14412;SY022522;A806053;J-508205;6-bromo-5-chloro-pyridin-3-ol

Chemical Property of 2-Bromo-3-chloro-5-hydroxypyridine

Chemical Property:

• Refractive Index: 1.629
• Boiling Point: 386.576 °C at 760 mmHg
• PKA: 7.91±0.10(Predicted)
• Flash Point: 187.595 °C
• PSA: 33.12000
• Density: 1.908g/cm³
• LogP: 2.20310
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 206.90865
• Heavy Atom Count: 9
• Complexity: 103

Purity/Quality:

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

2-Bromo-3-chloro-5-hydroxypyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=NC(=C1Cl)Br)O

Technology Process of 2-Bromo-3-chloro-5-hydroxypyridine

There total 5 articles about 2-Bromo-3-chloro-5-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: 60.0%

Acetic acid 6-bromo-5-chloro-pyridin-3-yl ester (130284-54-7) → 5-chloro-6-bromopyridine-3-ol (130284-56-9)

Guidance literature:

With potassium hydroxide; at 5 ℃; for 0.5h;

DOI:10.1055/s-1990-26919

Reference yield:

5-nitro-2-hydroxypyridine (5418-51-9) → 5-chloro-6-bromopyridine-3-ol (130284-56-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / aq. KClO₃, conc. HCl / 0.25 h / 50 - 60 °C

2: 90 percent / POBr₃, quinoline / 2 h / 120 °C

3: 81 percent / Fe, AcOH / H₂O / 2 h / below 50 deg C

4: 1) HBF₄, NaNO₂ / 1)water, 0 deg C, 1 h, 2) 70 deg C, 1 h

5: 60 percent / 2 N KOH / 0.5 h / 5 °C

With quinoline; hydrogenchloride; potassium hydroxide; tetrafluoroboric acid; potassium chlorate; iron; acetic acid; sodium nitrite; phosphorus(V) oxybromide; In water;

DOI:10.1055/s-1990-26919

Reference yield:

3-chloro-2-hydroxy-5-nitropyridine (22353-38-4) → 5-chloro-6-bromopyridine-3-ol (130284-56-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / POBr₃, quinoline / 2 h / 120 °C

2: 81 percent / Fe, AcOH / H₂O / 2 h / below 50 deg C

3: 1) HBF₄, NaNO₂ / 1)water, 0 deg C, 1 h, 2) 70 deg C, 1 h

4: 60 percent / 2 N KOH / 0.5 h / 5 °C

With quinoline; potassium hydroxide; tetrafluoroboric acid; iron; acetic acid; sodium nitrite; phosphorus(V) oxybromide; In water;

DOI:10.1055/s-1990-26919

upstream raw materials:

Acetic acid 6-bromo-5-chloro-pyridin-3-yl ester

5-nitro-2-hydroxypyridine

3-chloro-2-hydroxy-5-nitropyridine

2-bromo-3-chloro-5-nitropyridine

Downstream raw materials:

1-(3-chloro-5-hydroxypyridin-2-yl)ethanone

Refernces