103698-10-8

Basic information

• Product Name: Methyl 3-nitroisonicotinate
• Synonyms: Methyl 3-nitroisonicotinate;4-Pyridinecarboxylic acid, 3-nitro-, Methyl ester;Methyl 3-nitropyridine-4-carboxylate;3-nitroisonicotinic acid Methyl ester;[7-(4-Amino-2-fluoro-phenoxy)-thieno[3,2-b]phridin-2-yl-pyrrolidin-1-yl]-methanone;Methyl 3-nitroisonicotinoate
• CAS NO: 103698-10-8
• Molecular Formula: C₇H₆N₂O₄
• Molecular Weight: 182.13354
• Mol File: 103698-10-8.mol

Chemical Properties

• Boiling Point: 278.6±20.0℃ (760 Torr)
• Flash Point: 122.3±21.8℃
• Appearance: /
• Density: 1.375±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.00422mmHg at 25°C
• Refractive Index: 1.557
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -0.92±0.18(Predicted)
• CAS DataBase Reference: Methyl 3-nitroisonicotinate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-nitroisonicotinate(103698-10-8)
• EPA Substance Registry System: Methyl 3-nitroisonicotinate(103698-10-8)

Safety Data

• Hazardous Substances Data: 103698-10-8(Hazardous Substances Data)

Usage

Uses

Methyl 3-Nitroisonicotinate is used in preparation of 2-chloro-3-pyridinamine derivatives.

InChI:InChI=1/C7H6N2O4/c1-13-7(10)5-2-3-8-4-6(5)9(11)12/h2-4H,1H3

Upstream product

• 2459-09-8 4-pyridinecarboxylic acid, methyl ester 

Downstream Products

• 55279-30-6 methyl 3-aminoisonicotinate 
• 28033-03-6 Methyl 2-amino-5-nitroisonicotinate 
• 59786-32-2 methyl 3-methoxy-4-pyridinecarboxylate 
• 876919-08-3 methyl 3-fluoropyridine-4-carboxylate 
• 928778-90-9 methyl 5-nitro-2-(phenylamino)pyridine-4-carboxylate 
• 960114-13-0 2-(4-methoxycarbonyl-3-pyridyl)-propanedioic acid dimethyl ester 
• 173435-41-1 methyl 3-amino-2-chloropyridine-4-carboxylate 
• 1352037-95-6 3-phenyl-2-(pyridin-4-yl)-1,7-naphthyridine 
• 55279-29-3 3-amino-pyridine-4-carbaldehyde 

Relevant articles and documents

Synthesis of novel 1,7-naphthyridines by Friedlaender condensation of pyridine substrates

The general ability of appropriate pyridyl compounds (aldehyde or ketone) to undergo Friedlaender condensation to give different 1,7-naphthyridines has been demonstrated. 2,4-Disubstituted 1,7-naphthyridine 8 was prepared from 3-amino-4-acetylpyridine (6) and ketone 4 (82%). The Friedlaender self-condensation of pyridyl substrate 6 is reported, as well. The dimer product, 2-(3-aminopyridin-4-yl)-4-methyl-1,7-naphthyridine (7), was obtained in 97% yield. 2-Aryl-and 2,3-diaryl-1,7-naphthyridines (16-18) were prepared from 3-aminoisonicotinaldehyde (13) and arylketones 4, 14, and 15 (28-71%). The key substrates 6 and 13 are readily available via the improved pyridine nitration method. Copyright

α-(3-Pyridyl)malonates: preparation and synthetic applications

Alkylation of aromatic rings is a major challenge in organic syntheses since more complex carbon skeletons can be constructed. The alkylation of pyridine by nucleophilic aromatic substitution of the nitro group in methyl 3-nitro-4-pyridylcarboxylate (1) w

Nitropyridyl isocyanates

We hereby report the first preparation of 3-nitro-4-pyridyl isocyanate 9 and 5-nitro-2-pyridyl isocyanate 18. They were formed by Curtius rearrangement of the corresponding acyl azides 8 and 17, prepared from methyl 3-nitro-4-pyridinecarboxylate 6 via the hydrazide 7 and 5-nitro-picolinic acid 16, respectively. The substrates 6 and 16 were generated by nitration of methyl 4-pyridinecarboxylate 5 and nitration and oxidation of 2-picoline 14. 3-Nitro-4-pyridyl isocyanate 9 can be stored in dry solution and is stable at room temperature for several weeks while 5-nitro-2-pyridyl isocyanate 18 was less stable and should be used for synthetic purposes immediately.

The synthesis of β-nitropyridine compounds

Pyridine and a number of substituted pyridines have been nitrated by reaction with N2O5 followed by reaction with an aqueous solution of SO2xH2O or NaHSO3. The dependence of the yields on the pH of the aqueous reaction medium, on the concentration of SO2xH2O-HSO3-, on addition of methanol to the aqueous phase, and on the reaction temperature were investigated. The yields obtained with NaHSO3 were: 3-nitropyridine 77%, 2-methyl-5-nitro-pyridine 36%, 3-methyl-5-nitropyridinc 24%, 3-acetyl-5-nitropyridine 18%, 5-nitropyridine-3-carboxylic acid 15%, 3-chloro-5-nitropyridine 11%, 4-methyl-3-nitropyridine 39%, 4-acetyl-3-nitropyridine 67%, 4-cyano-3-nitropyridine 45%, 4-phenyl-3-nitropyridine 68%, 4-formyl-3-nitropyridine 62% (from reaction in liquid SO2), 3-nitropyridine-4-carboxylic acid 48%, methyl 3-nitropyridine-4-carboxylate 75%, 2,3-dimethyl-5-nitropyridine 37%, 2,4-dimethyl-5-nitropyridine 64%, 3-nitroquinoline 10% and 4-nitroisoquinoline 42%.