18344-51-9

Basic information

• Product Name: 2-Amino-3-methyl-5-nitropyridine
• Synonyms: 2-AMINO-3-METHYL-5-NITROPYRIDINE;2-AMINO-5-NITRO-3-PICOLINE;3-METHYL-5-NITRO-PYRIDINE-2-YLAMINE;3-METHYL-5-NITROPYRIDIN-2-AMINE;3-METHYL-5-NITRO-PYRIDIN-2-YLAMINE;TIMTEC-BB SBB005535;2-Bromo-5-Nitro-3-Methyl Pyridine;3-Methyl-5-nitro-pyridin-2-ylamin
• CAS NO: 18344-51-9
• Molecular Formula: C₆H₇N₃O₂
• Molecular Weight: 153.14
• EINECS: 1312995-182-4
• Product Categories: Pyridine;Pyridine series;Pyridines;Heterocyclic Compounds;Bases & Related Reagents;Heterocycles;Nucleotides;Boronic Acid;Furans
• Mol File: 18344-51-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 249-253 °C
• Boiling Point: 276.04°C (rough estimate)
• Flash Point: 173.6 °C
• Appearance: White to yellow crystalline powder.
• Density: 1.3682 (rough estimate)
• Vapor Pressure: 1.8E-05mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: Room temperature.
• PKA: 3.13±0.49(Predicted)
• BRN: 126947
• CAS DataBase Reference: 2-Amino-3-methyl-5-nitropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-3-methyl-5-nitropyridine(18344-51-9)
• EPA Substance Registry System: 2-Amino-3-methyl-5-nitropyridine(18344-51-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22-41-22
• Safety Statements: 36/37/39-26-22-39-36-37
• RIDADR: UN2811
• WGK Germany: 1
• HazardClass: IRRITANT
• Hazardous Substances Data: 18344-51-9(Hazardous Substances Data)

Usage

Chemical Properties

White to yellow crystalline powder.

InChI:InChI=1/C6H7N3O2/c1-4-2-5(9(10)11)3-8-6(4)7/h2-3H,1H3,(H2,7,8)/p+1

Upstream product

• 1603-40-3 3-methylpyridin-2-ylamine 
• 3599-89-1 propionamidine hydrochloride 
• 14080-32-1 5-nitropyrimidine 
• 6960-20-9 3-methyl-5-nitropyridine 
• 18344-53-1 3-methyl-2-nitraminopyridine 
• 7664-93-9 sulfuric acid 

Downstream Products

• 99989-57-8 N-(3-methyl-5-nitro-[2]pyridyl)-benzenesulfonamide 
• 21901-34-8 2-hydroxy-3-methyl-5-nitropyridine 
• 22280-56-4 2-chloro-3-methyl-5-nitropyridine 
• 1010108-59-4 methyl 4-[[4-(methoxycarbonyl)benzoyl](3-methyl-5-nitro-2-pyridinyl)amino]carbonylbenzenecarboxylate 
• 1266336-13-3 di-tert-butyl (3-methyl-5-nitro-pyridin-2-yl)imidodicarbonate 
• 1266336-04-2 tert-butyl (2-{(1S,2S)-2-[1-(5-chloro-pyrimidin-2-yl)-piperidin-4-yl]-cyclopropyl}-ethyl)-(3-methyl-5-nitro-pyridin-2-yl)-carbamate 
• 1230637-09-8 tert-butyl (3-methyl-5-nitropyridin-2-yl)carbamate 
• 106070-58-0 2,5-diamino-3-methylpyridine 
• 70-58-6 5-fluoropyridine-3-carboxamide 
• 402-66-4 5-fluoropyridine-3-carboxylic acid 
• 350-04-9 5-fluoro-3-pyridinecarbonyl chloride 
• 3430-19-1 5-methylpyridin-3-amine 
• 407-21-6 5-methyl-3-fluoropyridine 

Relevant articles and documents

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Selective vicarious nucleophilic amination of 3-nitropyridines

Nine 3-nitropyridine compounds and 4-nitroisoquinoline have been aminated in the 6-position (for 4-nitroisoquinoline in the 1-position) by vicarious nucleophilic substitution reactions. Two amination reagents were used, hydroxylamine and 4-amino-1,2,4-triazole. The yields were from moderate to good. Use of hydroxylamine gave an easy work-up procedure by which almost pure product was obtained directly, but 4-amino-1,2,4-triazole gave better yields of the aminated product for some of the substrates. By this, a general method for the preparation of 3- or 4-substituted-2-amino-5-nitropyridines was obtained.

Ring Transformations in Reactions of Heterocyclic Compounds with Nucleophiles. Conversion of 5-Nitropyrimidine into 2-Substituted 5-Nitropyrimidine and 2-Amino-5-nitropyridines by Amidines

The reaction of 5-nitropyrimidine (1) with benzamidine, pivalamidine, acetamidine, propionamidine, α-phenylacetamidine, O-methylisourea hydrochlorides, and cyanamide in ethanolic solution in the presence of triethylamine has been investigated.It was found that reaction of 1 with alkyl(aryl) amidines, having no active methylene groups attached to the amidine moiety (pivalamidine, benzamidine), exclusively formed the corresponding 2-substituted 5-nitropyrimidines in good yields.With acetamidine and propionamidine, in addition to the formation of the 2-substituted 5-nitropyrimidines, the formation of 2-amino-5-nitropyridines also was observed; with α-phenylacetamidine a 2-amino-5-nitropyridine derivative exclusively was obtained.The reaction of 1 with both O-methylisourea and cyanamide leads to 2-amino-5-nitropyrimidine.These reactions provide new examples of degenerate ring transformations of the pyrimidine ring system and of the ring transformation of pyrimidines into pyridines.