6635-86-5

Basic information

• Product Name: 2-Amino-3-nitro-4-picoline
• Synonyms: 4-Methyl-3-nitro-2-pyridinamine;TIMTEC-BB SBB006636;2-AMINO-4-METHYL-3-NITROPYRIDINE;2-AMINO-3-NITRO-4-METHYLPYRIDINE;2-AMINO-3-NITRO-4-PICOLINE;2-PYRIDINAMINE, 4-METHYL-3-NITRO-;4-METHYL-3-NITRO-PYRIDIN-2-YLAMINE;2-amin-3-nitro-4-methylpyridine
• CAS NO: 6635-86-5
• Molecular Formula: C₆H₇N₃O₂
• Molecular Weight: 153.14
• EINECS: -0
• Product Categories: Pyridine;Pyridine series;Pyridines;Boronic Acid;Amines;Aromatics;Heterocycles;Heterocycle-Pyridine series;amine |nitro-compound
• Mol File: 6635-86-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 136-140 °C(lit.)
• Boiling Point: 276.04°C (rough estimate)
• Flash Point: 139.3 °C
• Appearance: Yellow/Crystalline Powder
• Density: 1.3682 (rough estimate)
• Vapor Pressure: 0.000756mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.97±0.47(Predicted)
• BRN: 139111
• CAS DataBase Reference: 2-Amino-3-nitro-4-picoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-3-nitro-4-picoline(6635-86-5)
• EPA Substance Registry System: 2-Amino-3-nitro-4-picoline(6635-86-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39-22
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 6635-86-5(Hazardous Substances Data)

Usage

Chemical Properties

light yellow crystal powder

Uses

2-Amino-4-methyl-3-nitropyridine was used in the synthesis of 2-amino-5-hydroxy-4-methyl-3-nitropyridine, 2-amino-4-hydroxymethyl-3-nitropyridine and 2-amino-4-methyl-3-nitropyridine-1-oxide by undergoing biotransformation by Cunninghamella elegans ATCC 26269.

General Description

The crystal structure of 2-amino-4-methyl-3-nitropyridine was elucidated.

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

Upstream product

• 695-34-1 2-Amino-4-methylpyridine 
• 33245-30-6 4-methyl-2-nitraminopyridine 
• 7664-93-9 sulfuric acid 

Downstream Products

• 53929-59-2 4-methyl-2,3-diaminopyridine 
• 21901-18-8 2-hydroxy-4-methyl-3-nitropyridine 
• 132272-52-7 ethyl 7-methyl-8-nitroimidazo<1,2-a>pyridine-2-carboxylate 
• 372094-25-2 N-(4-Methyl-3-nitropyridin-2-yl)-(2-chloro-5-nitrophenyl)carboxamide 
• 3073-30-1 3,5-dinitropyridin-2-amine 
• 25782-40-5 2-amino-4-methyl-3,5-dinitro-pyridine 
• 676445-24-2 N-(4-bromo-2-fluorobenzyl)-4-methyl-3-nitropyridin-2-amine 
• 120494-13-5 methyl-4 phenyl-6 pyrido<3,2-e>pyrrolo<1,2-a>pyrazine 
• 120494-06-6 amino-3 methyl-4 (pyrrolyl-1)-2 pyridine 
• 120494-15-7 bromure de 5H-methyl-4 phenyl-6 pyrido<3,2-e>pyrrolo<1,2-a>pyrazinium 
• 120494-08-8 benzoylamino-3 methyl-4 (pyrrolyl-1)-2 pyridine 

Relevant articles and documents

Theoretical and experimental NMR data of 3,5-dinitro-2-(2-phenylhydrazinyl) pyridine and of its 4- and 6-methyl derivatives

3,5-Dinitro-2-(2-phenylhydrazinyl)pyridine and its methyl derivatives: 4-methyl-3,5-dinitro-2-(2-phenylhydrazinyl)pyridine and 6-methyl-3,5-dinitro-2- (2-phenylhydrazinyl)pyridine were synthesized and characterized by 1H NMR and 13C NMR. Calculations were also performed where the above molecules were optimized using the methods of density functional theory (DFT) with 6-31G(d,p) and 6-311G(d,p) basis sets. For all molecules studied, the lowest energy was obtained using the 6-311G(d,p) basis set. The GIAO/DFT (Gauge Invariant Atomic Orbitals/Density Functional Theory) calculations on the 6-311G and 6-311++G and 6-311G* basis sets were carried out to determine proton and carbon chemical shifts and to find they were close to the experimental values. It has been also found that intramolecular hydrogen bonding exists between hydrogen atom (in 2-NH group) and oxygen atom (pyridine-3-NO2). Moreover, resonances between pyridine ring and electron withdrawing 3-nitro group as well between that ring and the lone electron pair of NH group favor a co-planarity of the structure; this means a chelate ring created by above-mentioned intramolecular hydrogen bond is almost co-planar with pyridine ring.

Synthesis of some fluorine-containing pyridinealdoximes of potential use for the treatment of organophosphorus nerve-agent poisoning

Fluoroheterocyclic aldoximes were screened as therapeutic agents for the treatment of anticholinesterase poisoning. 2-Fluoropyridine-3- and -6-aldoxime, and 3-fluoropyridine-2- and -4-aldoxime, were synthesised. Attempts to obtain 3,5,6-trifluoropyridine-2,4-bis(aldoxime) and -2-aldoxime, however, proved unsuccessful. Pentafluorobenzaldoxime was prepared by oximation of pentafluorobenzaldehyde. Acid dissociation constants (pKa) and second-order rate constants (kox-) of the fluorinated pyridinealdoximes towards sarin were measured. 2,3,5,6-Tetrafluoropyridine-4- aldoxime had the best profile: its kox- approached that of the therapeutic oxime P2S (310 vs. 120 l mol-1 min-1), but its higher pKa (9.1 vs. 7.8) fell short of the target figure of 8 required for reactivation of inhibited acetylcholinesterase in vivo. N-alkylation of the fluorinated pyridine-aldoximes may reduce their pK a nearer to 8 and enhance their therapeutic potential. Crown Copyright

SYNTHESES WITH AROMATIC NITRAMINES, VI SUBSTITUENT EFFECT IN THE PHOTOLYTIC REARRANGEMENT OF NITRAMINOPYRIDINES

All isomeric ring-substituted methyl-2-nitraminopyridines, both 3-nitro- and 5-nitro-2-nitraminopyridines, 5-chloro- and 3-carboxy-2-nitraminopyridines, as well as 3,5-dibromo-2-nitraminopyridine were photolyzed in methanol by irradiation with a low-pressure mercury lamp (253.7 nm).Preference was generally noted for the migration of the side-chain nitro group to the vicinal β-position. 3,5-Dibromo-2-nitraminopyridine gave both 2-amino-3,5-dibromopyridine and 3,5-dibromopyridine-2-one.The ratio of the preparative and quantum yields of the two products were 2.5 and 3.0, respectively.