67242-59-5

Basic information

• Product Name: N-METHYL-N-(2-PYRIDYL)FORMAMIDE
• Synonyms: N-Methyl-N-(pyridin-2-yl)formamide;N-Methyl-N-(2-pyridyl)formamide;N-Methyl-N-(pyridin-2-yl);N-METHYL-N-(2-PYRIDYL)FORMAMIDE;2-(N-FORMYL-N-METHYLAMINO)PYRIDINE;MEYER'S REAGENT;MEYERS' REAGENT;N-formyl-N-methylaminopyridine
• CAS NO: 67242-59-5
• Molecular Formula: C₇H₈N₂O
• Molecular Weight: 136.15
• EINECS: 266-616-9
• Mol File: 67242-59-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 71-72 °C0.05 mm Hg(lit.)
• Flash Point: 229 °F
• Appearance: /
• Density: 1.137 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0009mmHg at 25°C
• Refractive Index: n20/D 1.566(lit.)
• PKA: 4.28±0.10(Predicted)
• BRN: 471767
• CAS DataBase Reference: N-METHYL-N-(2-PYRIDYL)FORMAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-METHYL-N-(2-PYRIDYL)FORMAMIDE(67242-59-5)
• EPA Substance Registry System: N-METHYL-N-(2-PYRIDYL)FORMAMIDE(67242-59-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 67242-59-5(Hazardous Substances Data)

Usage

Description

N-METHYL-N-(2-PYRIDYL)FORMAMIDE, also known as Meyers formylating agent, is an organic compound that serves as a versatile reagent in various chemical reactions. It is characterized by its ability to act as a formylating agent, which is crucial for the synthesis of a wide range of organic compounds.

Uses

Used in Organic Synthesis:
N-METHYL-N-(2-PYRIDYL)FORMAMIDE is used as a reactant for the preparation of Grignard reagents. Grignard reagents are important in organic chemistry for their ability to add to carbonyl groups, facilitating the formation of new carbon-carbon bonds and contributing to the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
N-METHYL-N-(2-PYRIDYL)FORMAMIDE is used as a reactant in the synthesis of 3-formyl-2-(4-methoxybenzyl)pyrazol-1-oxide. N-METHYL-N-(2-PYRIDYL)FORMAMIDE has potential applications in the development of pharmaceuticals, particularly those targeting specific biological pathways or receptors, due to its unique structural features that can be fine-tuned for medicinal chemistry purposes.

InChI:InChI=1/C7H8N2O/c1-9(6-10)7-4-2-3-5-8-7/h2-6H,1H3

Upstream product

• 4597-87-9 2-(N-methylamino)pyridine 
• 124-38-9 carbon dioxide 
• 504-29-0 2-aminopyridine 
• 2258-42-6 formyl acetic anhydride 
• 34813-97-3 2-(formylamino)pyridine 
• 74-88-4 methyl iodide 
• 64-18-6 formic acid 

Downstream Products

• 14160-91-9 4,6-dichloro-2-methyl-pyrimidine-5-carbaldehyde 
• 1333147-69-5 5-(benzyloxy)-3-bromo-1-methyl-6-oxo-1,6-dihydropyridine-2-carbaldehyde 
• 1197054-78-6 5-[4-(tert-butyldimethylsilyloxy)benzyl]-1-methyl-1H-imidazole-4-carbaldehyde 
• 850074-18-9 5-formyl-benzo[b]thiophene-2-carboxylic acid ethyl ester 
• 160278-07-9 5-(2-Formylphen-1-yl)-2-trityltetrazole 
• 3034-50-2 4⁽⁵⁾formylimidazole 
• 1027039-30-0 4-bromo-2-(4-methoxy-benzyl)-1-oxy-5-trimethylsilanyl-2H-pyrazole-3-carbaldehyde 
• 134420-45-4 1-(benzyloxy)methyl-5-formyl-4-iodoimidazole 
• 155601-65-3 2,6-difluoropyridine-3-carbaldehyde 
• 4597-87-9 2-(N-methylamino)pyridine 
• 5773-56-8 1,2-Diphenylethanol 
• 61077-65-4 1-phenylpent-4-en-2-ol 
• 6052-66-0 1-phenyl-3-buten-2-ol 
• 105735-62-4 3,3-dimethyl-1-phenyl-2-butanol 

Relevant articles and documents

Zinc Powder Catalysed Formylation and Urealation of Amines Using CO2 as a C1 Building Block?

Transformation of CO2 into valuable organic compounds catalysed by cheap and biocompatible metal catalysts is one of important topics of current organic synthesis and catalysis. Herein, we report the zinc powder catalysed formylation and urealation of amines with CO2 and (EtO)3SiH under solvent free condition. Using 2 molpercent zinc powder as the catalyst, a series of secondary amines, both the aromatic ones and the aliphatic ones, can be formylated into formamides. When primary aromatic amines were used as the substrates, the reactions produce urea derivatives. The electronic and steric effects from the substrates on the formylation and urealation reactions were observed and discussed. The recovery and reusability of zinc powder were investigated, showing the zinc powder can be reused in the formylation reaction without loss of catalytic activity. The analysis on the reactants/products mixture after filtering out the zinc powder showed the zinc concentration in the mixture is low to 1 ppm. The pathways for the formylation and urealation of amines with this catalytic system were also investigated, and related to the different substrates.

Iron-Catalyzed Selective N-Methylation and N-Formylation of Amines with CO2

We herein describe an efficient iron-catalyzed selective N-methylation and N-formylation of amines with CO2 and silane using mono-phosphine as ligand. With commercially available [CpFe(CO)2]2 as catalyst, Fe-catalyzed methylation of amines was achieved with triphenylphosphine as a ligand. Using tributylphosphine as a ligand, Fe-catalyzed formylation of amines was realized at a lower temperature. The method was successfully applied in the late-stage methylation and formylation of drug molecules containing amine moiety. (Figure presented.).

Ru-catalyzed hydroamidation of alkenes and cooperative aminocarboxylation procedure with chelating formamide

(Matrix presented) A strategy of chelation-assisted activation of formamide was employed to achieve hydroamidation of alkenes to generate one-carbon-elongated amides in moderate to good selectivity and yields. Also reported is the two-metal-catalyzed cooperative aminocarboxylation of aryl iodides, in which Ru is presumed to catalyze decarbonylation of formamide to release carbon monoxide and amine for the subsequent Pd-catalyzed aminocarboxylation routes, thus enabling the net transformation to be performed in the absence of external CO pressure.