39745-39-6

Basic information

• Product Name: 6-Hydroxy-5-nitro-2-picoline
• Synonyms: HYDROXY-6-METHYL-3-NITROPYRIDINE;6-METHYL-3-NITRO-2(1H)-PYRIDINONE;6-METHYL-3-NITRO-PYRIDIN-2-OL;6-HYDROXY-5-NITRO-2-PICOLINE;3-NITRO-6-METHYLPYRIDIN-2-OL;2-HYDROXY-6-METHYL-3-NITROPYRIDINE;2-HYDROXY-3-NITRO-6-METHYLPYRIDINE;2-HYDROXY-3-NITRO-6-PICOLINE
• CAS NO: 39745-39-6
• Molecular Formula: C₆H₆N₂O₃
• Molecular Weight: 154.12
• Product Categories: compounds of pyridine;blocks;Pyridines;Pyridine;Pyridines derivates
• Mol File: 39745-39-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 225-226 C
• Boiling Point: 277.46°C (rough estimate)
• Flash Point: 169.2 °C
• Appearance: Yellow crystalline powder
• Density: 1.4564 (rough estimate)
• Vapor Pressure: 2.97E-05mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 8.47±0.10(Predicted)
• CAS DataBase Reference: 6-Hydroxy-5-nitro-2-picoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Hydroxy-5-nitro-2-picoline(39745-39-6)
• EPA Substance Registry System: 6-Hydroxy-5-nitro-2-picoline(39745-39-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 37/39-26-36-39
• WGK Germany: 3
• Hazardous Substances Data: 39745-39-6(Hazardous Substances Data)

Usage

Chemical Properties

Yellow crystalline powder

InChI:InChI=1/C6H6N2O3/c1-4-2-3-5(8(10)11)6(9)7-4/h2-3H,1H3,(H,7,9)

Upstream product

• 70959-85-2 ethyl 2-amino-6-methylnicotinate 
• 109-06-8 α-picoline 
• 1824-81-3 2-Amino-6-methylpyridine 
• 21901-29-1 6-amino-5-nitro-2-picoline 
• 1556-32-7 1,3-dinitroquinolizin-4-one 
• 67-64-1 acetone 
• 14011-21-3 2-nitroacetamide 
• 41125-09-1 3-oxo-butyraldehyde; sodium enolate 
• 56057-19-3 2-chloro-6-methyl-3-nitropyridine 
• 3279-76-3 6-hydroxy-2-methylpyridine 

Downstream Products

• 52334-79-9 2-hydroxy-6-methyl-3-aminopyridine 
• 374633-31-5 2-bromo-6-methyl-3-nitropyridine 
• 56057-19-3 2-chloro-6-methyl-3-nitropyridine 
• 313950-14-0 6-methyl-2-piperidyl-3-pyridylamine 
• 179010-39-0 6-methyl-3-nitro-2-piperidylpyridine 
• 1027251-06-4 6-methyl-2-(2-phenylethynyl)-2-piperidyl-3-pyridylamine 
• 52334-80-2 3-benzoylamino-6-methyl-2-pyridone 
• 475272-62-9 6-methoxy-5-nitropicolinic acid 
• 112163-03-8 5-nitro-6-methoxy-2-methylpyridine 
• 353277-27-7 6-chloro-5-nitropyridine-2-carboxylic acid 
• 28489-45-4 6-methyl-5-nitropyridin-2-ol 

Relevant articles and documents

Phenacylation of 6-methyl-beta-nitropyridin-2-ones and further heterocyclization of products

Reaction between the derivatives of 6-methyl-beta-nitropyridin-2-one and phenacyl bromides was studied, and the yields observed were extremely low. The pyridones were converted via chloropyridines to methoxyderivatives, which were N-phenacylated. N-Phenacyl derivatives of 4,6-dimethyl-5-nitropyridin-2-one under the action of base gave 5-hydroxy-8-nitroindolizine and under acidic conditions gave 5-methyl-6-nitrooxazole[3,2-a]pyridinium salt, which underwent recycization with MeONa to 5-methoxy-8-nitroindolizine.

Synthetic equivalent of α-nitroformylacetic acid

A novel synthetic procedure for 3-nitro-2-pyridone derivatives (2) is provided, which includes the ring transformation of 1,3-dinitroquinolizin-4-one (3) with ketones in the presence of ammonium acetate.

Versatile synthesis of 6-substituted 8-deazapteridine-2,4-diamines. Formal total synthesis of 8,10-dideazaminopterin

A new synthesis of 4-amino-4-deoxy-8,10-dideazapteroic acid (11d) and 6-substituted and 5,6-anellated 8-deazapteridine-2,4-diamines, 10a, 10d, 25, is described. Starting from keteneaminals 1 or 12 and enaminones 4 or β-aminoketone 17 the title compounds can be prepared via functional group transformation of 2-amino-3-nitropyridines 5 or nicotinate 13a yielding 3-amino-α-picolinonitriles 9 which are cyclocondensed with guanidine.