164513-38-6

Basic information

• Product Name: 5-BROMO-2-HYDROXY-4-METHYLPYRIDINE
• Synonyms: 2-HYDROXY-4-METHYL-5-BROMOPYRIDINE;5-BROMO-2-HYDROXY-4-METHYLPYRIDINE;5-BROMO-2-HYDROXY-4-PICOLINE;5-BROMO-4-METHYLPYRIDIN-2-OL;5-BROMO-4-METHYL-2(1H)-PYRIDINONE;5-BROMO-4-METHYL-2-PYRIDINOL;5-Bromo-4-methylpyridin-2-ol, 5-Bromo-2-hydroxy-4-picoline;2-HYDROXY-5-BROMO-4-PICOLINE
• CAS NO: 164513-38-6
• Molecular Formula: C₆H₆BrNO
• Molecular Weight: 188.02
• Product Categories: blocks;Bromides;Pyridines;Pyridine;Heterocycle-Pyridine series
• Mol File: 164513-38-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 198-202 °C(lit.)
• Boiling Point: 339.893 °C at 760 mmHg
• Flash Point: 159.362 °C
• Appearance: Off-white/Solid
• Density: 1.5296 (rough estimate)
• Vapor Pressure: 0.0019mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 9.99±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 5-BROMO-2-HYDROXY-4-METHYLPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2-HYDROXY-4-METHYLPYRIDINE(164513-38-6)
• EPA Substance Registry System: 5-BROMO-2-HYDROXY-4-METHYLPYRIDINE(164513-38-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41
• Safety Statements: 26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 164513-38-6(Hazardous Substances Data)

Usage

Chemical Properties

light yellow powder

Uses

It is used for medicine.

InChI:InChI=1/C6H6BrNO/c1-4-2-6(9)8-3-5(4)7/h2-3H,1H3,(H,8,9)

Upstream product

• 13466-41-6 2-hydroksy-4-methyl-pyridine 
• 98198-48-2 2-amino-5-bromo-4-methylpyridine 

Downstream Products

• 164513-39-7 5-bromo-2-methoxy-4-methylpyridine 
• 163914-13-4 3-bromo-4-bromomethyl-6-methoxypyridine 
• 847349-87-5 2-(benzyloxy)-5-bromo-4-methylpyridine 
• 1079352-13-8 5-bromo-2-(difluoromethoxy)-4-methylpyridine 
• 778611-64-6 5-bromo-2-chloro-4-methylpyridine 
• 1383001-33-9 methyl 1-{[(5-bromo-4-methylpyridin-2-yl)oxy]-methyl}cyclopropanecarboxylate 
• 1383001-19-1 ethyl 1-{[(5-bromo-4-methylpyridin-2-yl)oxy]methyl}cyclobutanecarboxylate 
• 1383001-20-4 ethyl 1-({[4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]oxy}methyl)cyclo-butanecarboxylate 
• 1383001-24-8 ethyl 1-{[(5-{3-fluoro-4-[4-(trifluoro-methyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]phenyl}-4-methyl-pyridin-2-yl)oxy]methyl}cyclobutanecarboxylate 
• 1383001-25-9 1-{[(5-{3-fluoro-4-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]phenyl}-4-methylpyridin-2-yl)oxy]methyl}cyclobutanecarboxylic acid 
• 1383001-26-0 1-{[(5-{3-fluoro-4-[5-(trifluoromethyl)-1H-imidazol-2-yl]phenyl}-4-methylpyridin-2-yl)oxy]methyl}cyclobutanecarboxylic acid 
• 1383001-34-0 methyl 1-({[4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]oxy}methyl)cyclopropanecarboxylate 
• 1383001-35-1 methyl 1-{[(5-{3-chloro-4-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]phenyl}-4-methylpyridin-2-yl)oxy]methyl}cyclopropanecarboxylate 
• 1383001-36-2 1-{[(5-{3-chloro-4-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]phenyl}-4-methylpyridin-2-yl)oxy]methyl}cyclopropanecarboxylic acid 

Relevant articles and documents

Efficient regioselective preparation of monobromo and bromoiodo hydroxy pyridines from dibromoderivatives via bromine-lithium exchange

Annular dibromination of hydroxypyridines with NBS in acetonitrile followed by bromine-lithium exchange with RLi and subsequent trapping with H2O or I2 afforded monobromo and bromoiodo derivatives in a completely regioselective way. Iodination of bromo hydroxypyridines with NIS is totally regioselective.

Preparation of E-(2-substituted-1-methylethylidene)indanones derived from monic acid

Alkylation of the lithium dienolate of the monic acid hydroxamate (3) with o-bromo(bromomethyl) benzene or heteroaromatic derivatives gave α-alkylated products (5). This alkylation procedure was surprisingly catalysed by 4- dimethylaminopyridine. Metal-halogen exchange with t-butyl lithium occurred with concomitant intramolecular cyclisation to give a mixture of the deconjugated ketones (6). Reconjugation with potassium t-butoxide stereoselectively produced the E-isomer (7). Deprotection gave the monic acid derived ketone (1).