3400-33-7

Basic information

• Product Name: N-Methylnaphthalene-1-carboxamide
• Synonyms: N-Methyl-1-naphthamide;N-Methylnaphthalene-1-carboxamide;1-Naphthalenecarboxamide, N-methyl-;N-methyl-1-Naphthalenecarboxamide
• CAS NO: 3400-33-7
• Molecular Formula: C₁₂H₁₁NO
• Molecular Weight: 185.2218
• Mol File: 3400-33-7.mol

Chemical Properties

• Boiling Point: 416.3°Cat760mmHg
• Flash Point: 247.2°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 3.86E-07mmHg at 25°C
• Refractive Index: 1.621
• CAS DataBase Reference: N-Methylnaphthalene-1-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methylnaphthalene-1-carboxamide(3400-33-7)
• EPA Substance Registry System: N-Methylnaphthalene-1-carboxamide(3400-33-7)

Safety Data

• Hazardous Substances Data: 3400-33-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Production:
N-Methylnaphthalene-1-carboxamide is utilized as an intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs due to its chemical reactivity and structural properties.
Used in Dye Manufacturing:
In the dye industry, N-Methylnaphthalene-1-carboxamide serves as a key component in the production of various dyes, leveraging its chemical structure to impart color and stability to the final products.
Used in Organic Synthesis:
N-Methylnaphthalene-1-carboxamide is employed as a building block in organic synthesis, enabling the creation of a wide range of organic compounds for different applications, from chemical research to industrial processes.
Used in Industrial Product Manufacturing:
N-Methylnaphthalene-1-carboxamide is incorporated into the manufacturing of various industrial products, where its chemical properties are harnessed to enhance performance or achieve specific functional requirements.
Used in Organic Electronics:
Owing to its electronic and optical properties, N-Methylnaphthalene-1-carboxamide is studied for potential applications in the field of organic electronics, where it could be used in the development of devices such as organic light-emitting diodes (OLEDs) or organic solar cells.
Used in Medicinal Applications:
N-Methylnaphthalene-1-carboxamide has demonstrated antimicrobial and anti-inflammatory activities, making it a potential candidate for use in medicinal applications, where it could contribute to the treatment of infections and inflammatory conditions.

InChI:InChI=1/C12H11NO/c1-13-12(14)11-8-4-6-9-5-2-3-7-10(9)11/h2-8H,1H3,(H,13,14)

Upstream product

• 74-89-5 methylamine 
• 879-18-5 naphthalene-1-carbonic acid chloride 
• 86-55-5 1-naphthalenecarboxylic acid 
• 13493-24-8 N-benzyl-N-methyl-1-naphthamide 
• 593-51-1 methylamine hydrochloride 
• 123-39-7 N-Methylformamide 
• 90-11-9 1-Bromonaphthalene 
• 14489-75-9 N-methyl-1-naphthalenemethylamine 
• 67-56-1 methanol 
• 86-53-3 1-Cyanonaphthalene 
• 13504-46-6 1-naphtylaldehyde oxime 
• 2243-81-4 1-naphthylcarboxamide 

Downstream Products

• 65473-13-4 N-methyl-1-naphthalenemethylamine hydrochloride 
• 14489-75-9 N-methyl-1-naphthalenemethylamine 
• 1613320-01-6 1-(methylcarbamoyl)naphthalen-2-yl 4-chlorobenzoate 
• 91161-71-6 terbinafin 
• 65472-88-0 naftifine 
• 1315257-15-8 2-methyl-3,4-diphenylbenzo[h]isoquinolin-1(2H)-one 
• 642-29-5 1-benzoylnaphthalene 
• 1402849-80-2 2-(4-methoxyphenyl)-N-methyl-1-naphthamide 
• 1402849-71-1 N-methyl-2-phenyl-1-naphthamide 

Relevant articles and documents

Palladium-Catalyzed Annulation of Arylbenzamides with Diaryliodonium Salts

By using diaryliodonium salts, a cylization has been accomplished in the synthesis of N-aryl phenanthridinone derivatives via a cascade of ortho-arylation and Csp2-N bond formation in the presence of palladium catalyst. The reaction exhibits a broad compatibility of readily available N-arylnaphthamides. (Figure presented.).

The Pd-catalyzed synthesis of difluoroethyl and difluorovinyl compounds with a chlorodifluoroethyl iodonium salt (CDFI)

Herein, we report a simple and efficient method for the direct installation of chlorodifluoroethyl group onto aromatic molecules of various aromatic amides with a new 2-chloro,2,2-difluoroethyl(mesityl)iodonium salt (CDFI). Moreover, the chlorodifluoroeth

Rhodium-Catalyzed Electrooxidative C?H Olefination of Benzamides

Metal-catalyzed chelation-assisted C?H olefinations have emerged as powerful tools for the construction of functionalized alkenes. Herein, we describe the rhoda-electrocatalyzed C?H activation/alkenylation of arenes. The olefinations of challenging electron-poor benzamides were thus accomplished in a fully dehydrogenative fashion under electrochemical conditions, avoiding stoichiometric chemical oxidants, and with H2 as the only byproduct. This versatile alkenylation reaction also features broad substrate scope and used electricity as a green oxidant.

Rhenium-Catalyzed Phthalide Synthesis from Benzamides and Aldehydes via C-H Bond Activation

The [4 + 1] annulation of benzamides and aldehydes for phthalide synthesis was achieved via rhenium-catalyzed C-H activation, which demonstrates an unprecedented reaction pattern distinct from those of other transition-metal catalyses. The reaction also features readily available starting materials, a wide scope for both electro-rich and electro-deficient substrates, and the elimination of homoannulation byproducts.

Tandem Transformation of Aldoximes to N-Methylated Amides Using Methanol

Tandem conversion of aldoximes to N-methylated amides with methanol in presence of a single Ru(II) catalyst is accomplished through the Ru(II)-mediated rearrangement followed by the reductive N-methylation. Employing this protocol, several aldoximes were directly transformed to the N-methylated amides using methanol. Kinetic experiments with H218O advocated that the aldoxime is acted as the nucleophile during the aldoxime to amide rearrangement process. Involvement of nitrile intermediate during this transformation is realized from the kinetic study. (Figure presented.).

Atom-Economical and Tandem Conversion of Nitriles to N-Methylated Amides Using Methanol and Water

A cobalt complex catalyzed tandem conversion of nitrile to N-methylated amide is described using a methanol and water mixture. Using this protocol, several nitriles were directly and efficiently converted to the desired N-methylated amides. Kinetic experiments using H2O18 and CD3OD suggested that water and methanol were the source of the oxygen atom and methyl group, respectively, in the final N-methylated amides. Importantly, the participation of active Co(I)-H species in this transformation was realized from the control experiment. The kinetic isotope effect (KIE) study suggested that the activation of the C-H bond of methanol was a kinetically important step. The Hammett plot confirmed that the reaction was faster with the electron deficient nitriles. In addition, the plausible pathway for the formation of N-methylated amides from the nitriles was supported by the computational study.

Ruthenium-Catalyzed Synthesis of N-Methylated Amides using Methanol

An efficient synthesis of N-methylated amides using methanol in the presence of a ruthenium(II) catalyst is realized. Notably, applying this process, tandem C-methylation and N-methylation were achieved to synthesize α-methyl N-methylated amides. In addition, several kinetic studies and control experiments with the plausible intermediates were performed to understand this novel protocol. Furthermore, detailed computational studies were carried out to understand the mechanism of this transformation.

Palladium-Catalyzed Direct C-H Trifluoroethylation of Aromatic Amides

A simple and direct C-H trifluoroethylation of aromatic amides has been developed. The protocol is applicable to a variety of aromatic amides, including ones derived from amino acids. The developed method can be used for further modifications of peptides. Preliminary mechanistic studies have been done by isolating the reaction intermediate.

I2-Catalyzed Oxidative Amidation of Benzylamines and Benzyl Cyanides under Mild Conditions

We report a novel and efficient method for the oxidation of benzylic carbons (amines and cyanides) into corresponding benzamides using a catalytic amount of I2 and TBHP as the green oxidant via the C-H bond cleavage of the benzylic carbon under mild reaction conditions. According to the literature survey, this is the first report for the oxidative amidation of benzylamines and decyanation of benzyl cyanides in one pot under metal-free conditions.

Ru(II)-Catalyzed C-H Activation: Amide-Directed 1,4-Addition of the Ortho C-H Bond to Maleimides

Maleimide has been used as a selective coupling partner to generate conjugate addition products exclusively. The typical Heck-type oxidative coupling that occurs when alkenes are used is avoided by choosing maleimide as an alkene, which cannot undergo β-hydride elimination due to the unavailability of a syn-periplanar β-hydrogen atom. The amide nitrogen, which is notorious for undergoing tandem reactions to generate spirocyclic or annulation products under cross-coupling conditions, remains innocent in this report. Along with the substrate scope, a robustness screen has been performed to analyze the performance of amide as a directing group in the presence of other directing groups and also to examine the tolerance of the reaction conditions for other frequently encountered functional groups.