38195-81-2

Basic information

• Product Name: 2-Pyridinecarboxylicacid,methylester,1-oxide(9CI)
• Synonyms: 2-Pyridinecarboxylicacid,methylester,1-oxide(9CI);Methyl 2-pyridinecarboxylate 1-oxide;1-Oxy-pyridine-2-carboxylicacidmethylester;2-(methoxycarbonyl)pyridine 1-oxide
• CAS NO: 38195-81-2
• Molecular Formula: C₇H₇NO₃
• Molecular Weight: 153.13538
• Product Categories: CARBOXYLICESTER
• Mol File: 38195-81-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 72-73 °C
• Boiling Point: 340.5±15.0 °C(Predicted)
• Appearance: /
• Density: 1.20±0.1 g/cm3(Predicted)
• PKA: -0.90±0.10(Predicted)
• CAS DataBase Reference: 2-Pyridinecarboxylicacid,methylester,1-oxide(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyridinecarboxylicacid,methylester,1-oxide(9CI)(38195-81-2)
• EPA Substance Registry System: 2-Pyridinecarboxylicacid,methylester,1-oxide(9CI)(38195-81-2)

Safety Data

• Hazardous Substances Data: 38195-81-2(Hazardous Substances Data)

Upstream product

• 824-40-8 2-pyridinecarboxylic acid N-oxide 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 98-98-6 2-Picolinic acid 
• 2459-07-6 methyl pyridine-2-carboxylate 
• 67-56-1 methanol 
• 186581-53-3 diazomethane 
• 2524-52-9 ethyl-2-picolinate 

Downstream Products

• 2459-07-6 methyl pyridine-2-carboxylate 
• 6636-55-1 methyl 6-chloropicolinate 
• 24484-93-3 4-Chloro-pyridine-2-carboxylic acid methyl ester 
• 30062-34-1 methyl 6-oxo-1,6-dihydropyridine-2-carboxylate 
• 54633-17-9 2-(hydrazinecarbonyl)pyridine-1-oxide 
• 6974-72-7 2-pyridinecarboxamide 1-oxide 
• 36052-26-3 methyl 6-aminopyridine-2-carboxylate 
• 32559-18-5 methyl piperidine-2-carboxylate hydrochloride 

Relevant articles and documents

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Hydroheteroarylation of Unactivated Alkenes Using N-Methoxyheteroarenium Salts

We report the first reductive coupling of unactivated alkenes with N-methoxy pyridazinium, imidazolium, quinolinium, and isoquinolinium salts under hydrogen atom transfer (HAT) conditions, and an expanded scope for the coupling of alkenes with N-methoxy pyridinium salts. N-Methoxy pyridazinium, imidazolium, quinolinium, and isoquinolinium salts are accessible in 1-2 steps from the commercial arenes or arene N-oxides (25-99%). N-Methoxy imidazolium salts are accessible in three steps from commercial amines (50-85%). In total 36 discrete methoxyheteroarenium salts bearing electron-donating, electron-withdrawing, alkyl, aryl, halogen, and haloalkyl substituents were prepared (several in multigram quantities) and coupled with 38 different alkenes. The transformations proceed under neutral conditions at ambient temperature, provide monoalkylation products exclusively, and form a single alkene addition regioisomer. Preparatively useful and complementary site selectivities in the addition of secondary and tertiary radicals to pyidinium salts are documented: harder secondary radicals favor C-2 addition (2->10:1), while softer tertiary radicals favor bond formation to C-4 (4.7->29:1). A diene possessing a 1,2-disubstituted and 2,2-disubstituted alkene undergoes hydropyridylation at the latter exclusively (61%) suggesting useful site selectivities can be obtained in polyene substrates. The methoxypyridinium salts can also be employed in dehydrogenative arylation, borono-Minisci, and tandem arylation processes. Mechanistic studies support the involvement of a radical process.

Ligands for copper-catalyzed C-N bond forming reactions with 1 Mol% CuBr as catalyst

Several new ligands were designed to promote copper-catalyzed Ullman C-N coupling reactions. In this group, 8-hydroxyquinolin-N-oxide was found to serve as a superior ligand for CuBr-catalyzed coupling reactions of aryl iodides, bromides, and chlorides with aliphatic amines and N-heterocycles under a low catalyst loading (1% [Cu] mol). Reactions with the inexpensive catalytic system display a high functional group tolerance as well as excellent chemoselectivity.