5-BroMo-4-hydroxynicotinic acid

Base Information

• Chemical Name: 5-BroMo-4-hydroxynicotinic acid
• CAS No.: 1052114-83-6
• Molecular Formula: C6H4BrNO3
• Molecular Weight: 218.007
• Hs Code.: 2933399090
• Mol file: 1052114-83-6.mol

Synonyms:5-BroMo-4-hydroxynicotinic acid;5-BroMo-4-hydroxypyridin-3-carboxylic acid;5-bromo-4-hydroxypyridine-3-carboxylic acid

Chemical Property of 5-BroMo-4-hydroxynicotinic acid

Chemical Property:

• Boiling Point: 452.0±45.0 °C(Predicted)
• PKA: -0.46±0.14(Predicted)
• PSA: 70.16000
• Density: 1.985±0.06 g/cm3(Predicted)
• LogP: 0.83560
• Storage Temp.: Inert atmosphere,Room Temperature

Purity/Quality:

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

5-Bromo-4-hydroxynicotinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-BroMo-4-hydroxynicotinic acid

There total 6 articles about 5-BroMo-4-hydroxynicotinic acid 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: 85.0%

n-butyllithium (109-72-8,29786-93-4) + 3,5-dibromo-4-hydroxypyridine (25813-25-6) + carbon dioxide (124-38-9,18923-20-1) → 5-bromo-4-hydroxypyridine-3-carboxylic acid (1052114-83-6)

Guidance literature:

3,5-dibromo-4-hydroxypyridine; With methyllithium; In tetrahydrofuran; diethyl ether; at -78 ℃; Inert atmosphere;

n-butyllithium; In tetrahydrofuran; diethyl ether; hexane; at -78 ℃; for 1.5h; Inert atmosphere;

carbon dioxide; In tetrahydrofuran; diethyl ether; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jm800476q

Reference yield: 70.19%

4-hydroxynicotinic acid (609-70-1) → 5-bromo-4-hydroxypyridine-3-carboxylic acid (1052114-83-6)

Guidance literature:

With bromine; In N,N-dimethyl-formamide; at 10 - 60 ℃;

Reference yield:

C9H14O3NC6H5 (41276-30-6) → 5-bromo-4-hydroxypyridine-3-carboxylic acid (1052114-83-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogen / acetonitrile / 4 h / 45 - 50 °C / 2250.23 - 3000.3 Torr / Autoclave

2.1: dihydrogen peroxide; hydrogen bromide / dichloromethane / 5 h / 40 - 45 °C

3.1: potassium carbonate / tetrahydrofuran / 3 h / 50 - 55 °C

3.2: 2 h / 20 - 35 °C

With hydrogen bromide; hydrogen; dihydrogen peroxide; potassium carbonate; In tetrahydrofuran; dichloromethane; acetonitrile;

upstream raw materials:

n-butyllithium

3,5-dibromo-4-hydroxypyridine

carbon dioxide

4-piperidone-3-carboxylic acid ethyl ester

Downstream raw materials:

methyl 5-bromo-4-oxo-1,4-dihydropyridine-3-carboxylate

N-{4-[2-amino-5-(3,4-dimethoxyphenyl)pyridin-3-yl]phenyl}-6'-fluoro-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydro-3,3'-bipyridine-5-carboxamide

Refernces

• 1、 -. "Preparation method of nicotinic acid derivative". Paragraph 0086-0089. . Retrieved 2019/12/02.
• 2、 Kyoung, Soon Kim,Zhang, Liping,Schmidt, Robert,Cai, Zhen-Wei,Wei, Donna,Williams, David K.,Lombardo, Louis J.,Trainor, George L.,Xie, Dianlin,Zhang, Yaquan,An, Yongmi,Sack, John S.,Tokarski, John S.,Darienzo, Celia,Kamath, Amrita,Marathe, Punit,Zhang, Yueping,Lippy, Jonathan,Jeyaseelan Sr., Robert,Wautlet, Barri,Henley, Benjamin,Gullo-Brown, Johnni,Manne, Veeraswamy,Hunt, John T.,Fargnoli, Joseph,Borzilleri, Robert M.. "Discovery of pyrrolopyridine-pyridone based inhibitors of met kinase: Synthesis, X-ray crystallographic analysis, and biological activities". experimental part. p. 5330 - 5341. Retrieved 2009/07/01.