5454-10-4

Basic information

• Product Name: 1-Naphthalenecarboxamide, N,N-diethyl-
• Synonyms: 1-Naphthalenecarboxamide, N,N-diethyl-;N,N-Diethylnaphthalene-1-carboxamide;1-Naphthamide, N,N-diethyl-
• CAS NO: 5454-10-4
• Molecular Formula: C₁₅H₁₇NO
• Molecular Weight: 227.3
• Product Categories: Miscellaneous Reagents
• Mol File: 5454-10-4.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 389.3°Cat760mmHg
• Flash Point: 180.3°C
• Appearance: /
• Density: 1.072g/cm³
• Refractive Index: 1.73
• CAS DataBase Reference: 1-Naphthalenecarboxamide, N,N-diethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Naphthalenecarboxamide, N,N-diethyl-(5454-10-4)
• EPA Substance Registry System: 1-Naphthalenecarboxamide, N,N-diethyl-(5454-10-4)

Safety Data

• Hazardous Substances Data: 5454-10-4(Hazardous Substances Data)

Usage

Description

1-Naphthalenecarboxamide, N,N-diethyl-, also known as N,N-Diethyl-1-naphthamide (CAS# 5454-10-4), is an organic compound derived from naphthalene. It is characterized by its oily chemical properties, which make it a versatile compound for various applications in the field of organic synthesis.

Uses

Used in Organic Synthesis:
1-Naphthalenecarboxamide, N,N-diethylis used as a synthetic intermediate for the production of various organic compounds. Its unique chemical structure allows it to be a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-Naphthalenecarboxamide, N,N-diethylis used as a key component in the development of new drugs. Its chemical properties enable it to interact with various biological targets, potentially leading to the discovery of novel therapeutic agents.
Used in Agrochemical Industry:
1-Naphthalenecarboxamide, N,N-diethylis also utilized in the agrochemical industry for the synthesis of new pesticides and other crop protection agents. Its unique structure can be tailored to target specific pests or diseases, contributing to the development of more effective and environmentally friendly solutions for agriculture.
Used in Specialty Chemicals:
In the specialty chemicals sector, 1-Naphthalenecarboxamide, N,N-diethylis employed in the production of various high-value chemicals, such as dyes, pigments, and additives. Its versatile chemical properties make it an attractive candidate for the development of innovative products with specific applications in various industries.

InChI:InChI=1/C13H9Br2N3O6/c1-24-8-4-6(14)9(15)5(11(8)19)2-3-7-10(18(22)23)12(20)17-13(21)16-7/h2-4,19H,1H3,(H2,16,17,20,21)

Upstream product

• 109-89-7 diethylamine 
• 879-18-5 naphthalene-1-carbonic acid chloride 
• 92636-17-4 11-Oxa-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5,9-tetraene-3-carboxylic acid diethylamide 
• 91-20-3 naphthalene 
• 88-10-8 N,N-diethylcarbamyl chloride 
• 201230-82-2 carbon monoxide 
• 90-11-9 1-Bromonaphthalene 
• 90-14-2 1-Iodonaphthalene 
• 86-55-5 1-naphthalenecarboxylic acid 
• 88769-13-5 N,N-diethyl-3-(trimethylsilyloxy)benzamide 
• 617-84-5 N-formyldiethylamine 
• 66-77-3 1-naphthaldehyde 
• 121-44-8 triethylamine 

Downstream Products

• 7495-38-7 phenanthro[3,2-b]thiophene-7,11-quinone 
• 87177-13-7 3-(1-Benzyl-1H-pyrrol-2-yl)-3H-naphtho[1,2-c]furan-1-one 
• 73540-71-3 12-Benzyl-12H-12-aza-indeno[1,2-b]phenanthrene-7,13-dione 
• 105259-55-0 3-Phenylsulfanyl-phenanthrene-1,4-dione 
• 3719-43-5 dibenzo[a,h]anthracene-7,14-dione 
• 5656-98-4 phenyl-3 naphtho<1,2c> furane(3H)one-1 
• 61533-50-4 dibenzanthracene-7,14-dione 
• 81194-76-5 3-methyl-3-phenyl-3H-naphtho[1,2-c]furan-1-one 

Relevant articles and documents

Palladium-Catalyzed C8-Oxygenation of Naphthalene Derivatives: Direct Access to Naphtholactone Skeleton

Herein, a direct C8-oxygenation of naphthalene derivatives is described. Different carbonyl groups were used as directing group to deliver corresponding naphthols via a palladium-catalyzed oxidation reaction using PhI(OAc)2 in a TFA/TFAA mixture. Interestingly, when Weinreb amide was employed as the directing group, the naphtholactone skeleton was directly obtained. This methodology was applied to the synthesis of variously substituted naphtholactones. (Figure presented.).

Palladium-Catalyzed C8-Arylation of Naphthalenes through C?H Activation: A Combined Experimental and Computational Study

Herein, a direct C8-arylation reaction of 1-amidonaphthalenes is described. By using diaryliodonium salts as arylating agents, the palladium-catalyzed C?H activation reaction showed perfect C8 regioselectivity and a wide functional group tolerance. In most cases, the desired polyaromatic compounds were isolated in good to excellent yields. To explain the observed regioselectivity, DFT calculations were performed and highlighted the crucial role of the amide directing group. Finally, the utility of this method is showcased by the synthesis of benzanthrone derivatives.

Pd/C-catalyzed aminocarbonylation of aryl iodides via oxidative C-N bond activation of tertiary amines to tertiary amides

This work reports oxidative N-dealkylation/carbonylation of tertiary amines to tertiary amides by using molecular oxygen as a sole oxidant using a Pd/C catalyst. This protocol is free from ligands, additives, bases, and cocatalysts. Different tertiary amines as well as aryl iodides have been examined for this transformation, providing desired products in good to excellent yield.