3-Bromo-2-hydroxypyridine

Base Information

• Chemical Name: 3-Bromo-2-hydroxypyridine
• CAS No.: 13466-43-8
• Molecular Formula: C5H4BrNO
• Molecular Weight: 173.997
• Hs Code.: 29337900
• European Community (EC) Number: 626-942-8
• DSSTox Substance ID: DTXSID30355959
• Nikkaji Number: J761.739I
• Wikidata: Q72457008
• Mol file: 13466-43-8.mol

Synonyms:3-Bromo-2-hydroxypyridine;13466-43-8;3-bromopyridin-2-ol;3-BROMOPYRIDIN-2(1H)-ONE;2-HYDROXY-3-BROMOPYRIDINE;3-Bromo-2-pyridinol;3-bromo-1H-pyridin-2-one;3-bromo-2(1H)-pyridinone;2(1H)-Pyridinone, 3-bromo-;MFCD03411569;3-Bromo-2-hydroxy-pyridine;bromopyridone;3-bromopyridone;monobromopyridone;bromohydroxypyridine;3-Bromo-2-pyridone;3-Bromo-pyridin-2-ol;3-bromo-1H-2-pyridone;SCHEMBL118163;YDUGVOUXNSWQSW-UHFFFAOYSA-;DTXSID30355959;3-Bromo-2-hydroxypyridine, 97%;HMS1653I21;BCP11402;cyclohex-4-ene-1,2-dicarboxylicacid;AKOS000320198;AKOS022381261;CS-W003045;FS-2164;PB12284;BP-20252;SY008491;AM20050778;B2330;FT-0645792;EN300-85458;AG-690/03080022;F1371-0174

Chemical Property of 3-Bromo-2-hydroxypyridine

Chemical Property:

• Appearance/Colour: Light yellow powder
• Vapor Pressure: 0.000111mmHg at 25°C
• Melting Point: 179-183 °C
• Refractive Index: 1.6
• Boiling Point: 336.6 °C at 760 mmHg
• PKA: 10.53±0.10(Predicted)
• Flash Point: 157.4 °C
• PSA: 33.12000
• Density: 1.776 g/cm³
• LogP: 1.54970
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1.1
• 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

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

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 26-36-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CNC(=O)C(=C1)Br
• Uses: 3-Bromo-2-hydroxypyridine is used in the synthesis of pyrazolopyridines as γ-secratase modulators. 3-Bromo-2-hydroxypyridine is sued as an active ingredient pharmaceuticals, in medicine.

Technology Process of 3-Bromo-2-hydroxypyridine

There total 13 articles about 3-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: 90.0%

2-Amino-3-bromopyridine (13534-99-1) → 3-bromo-pyridin-2-ol (13466-43-8)

Guidance literature:

With sulfuric acid; sodium nitrite; In water; at 0 ℃; for 1h;

DOI:10.1021/acs.orglett.6b01263

Reference yield: 78.0%

2-hydroxypyridin (142-08-5) → 3-bromo-pyridin-2-ol (13466-43-8)

Guidance literature:

With bromine; potassium bromide; In water; at 20 ℃; for 24.25h;

Reference yield: 78.0%

2-Pyridone (142-08-5,1199357-22-6) → 3-bromopyridin-2(1H)-one (13466-43-8)

Guidance literature:

With bromine; potassium bromide; In water; for 24h; Rate constant; Mechanism; Product distribution; different reaction conditions, pH dependence;

DOI:10.1021/ja00379a016

upstream raw materials:

acetic acid-(3-bromo-[2]pyridyl ester)

2-hydroxypyridin

3,5-dibromo-2-hydroxypyridine

2-Amino-3-bromopyridine

Downstream raw materials:

3-Bromo-2-methoxypyridine

3-chloro-2-hydroxypyridine

3-bromo-5-iodopyridin-2-ol

3-bromo-1-methyl-1H-pyridin-2-one

Refernces

• 1、 Idzik, Tomasz J.,Borzyszkowska-Ledwig, Aleksandra,Struk, ?ukasz,So?nicki, Jacek G.. "Magnesiate-Utilized/Benzyne-Mediated Approach to Indenopyridones from 2-Pyridones: An Attempt to Synthesize the Indenopyridine Core of Haouamine". supporting information. p. 9667 - 9671. Retrieved 2019/11/29.
• 2、 Schwertz, Geoffrey,Witschel, Matthias C.,Rottmann, Matthias,Bonnert, Roger,Leartsakulpanich, Ubolsree,Chitnumsub, Penchit,Jaruwat, Aritsara,Ittarat, Wanwipa,Sch?fer, Anja,Aponte, Raphael A.,Charman, Susan A.,White, Karen L.,Kundu, Abhijit,Sadhukhan, Surajit,Lloyd, Mel,Freiberg, Gail M.,Srikumaran, Myron,Siggel, Marc,Zwyssig, Adrian,Chaiyen, Pimchai,Diederich, Fran?ois. "Antimalarial Inhibitors Targeting Serine Hydroxymethyltransferase (SHMT) with in Vivo Efficacy and Analysis of their Binding Mode Based on X-ray Cocrystal Structures". supporting information. p. 4840 - 4860. Retrieved 2017/06/28.