5454-10-4

Usage

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

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

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 
• 105259-55-0 3-Phenylsulfanyl-phenanthrene-1,4-dione 
• 5656-98-4 phenyl-3 naphtho<1,2c> furane(3H)one-1 
• 66-77-3 1-naphthaldehyde 
• 81194-85-6 2-(1-phenyl-ethyl)-[1]naphthoic acid 
• 17526-28-2 acetic acid-(7-methyl-benz[a]anthracen-12-yl ester) 
• 224-41-9 dibenz[a,j]anthracene 
• 53-70-3 dibenzo[a,h]anthracene 
• 2541-69-7 7-methylbenz[a]anthracene 
• 152123-69-8 2-<(2-(Carboxymethyl)-3-methylphenyl)methyl>naphthoic acid 
• 173852-22-7 2-(hydroxy-phenyl-methyl)-naphthalene-1-carboxylic acid diethylamide 
• 82-60-0 naphtho[2,1-b]thiophen-1-ol 
• 866784-28-3 1-(1-hydroxynaphtho[2,1-b]thiophen-2-yl)-3-phenylprop-2-en-1-one 

Relevant academic research and scientific papers

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 N-Acylation of Tertiary Amines by Carboxylic Acids: A Method for the Synthesis of Amides

A palladium-catalyzed N-acylation of tertiary amines by carboxylic acids was achieved through C-N cleavage. This reaction showed a wide substrate scope. Both aromatic and aliphatic acids served well as the acylating reagents and coupled with tertiary amines to produce the corresponding amides in good to excellent yields. With the strategy, bioactive carboxylic acids were also efficiently modified, highlighting the synthetic value of the process in organic synthesis.

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.

Amide-Directed Ru-Catalyzed Hydrodemethoxylation of ortho-Methoxy-Benzamides and -Naphthamides: A D oM Reaction Counterpart

A new ruthenium-catalyzed hydrodemethoxylation of ortho-methoxy-benzamides and -naphthamides involving amide-directed C-OMe bond activation and hydride reduction is disclosed. The reaction is general, proceeding under RuH2(CO)(PPh3)3 catalysis using either triethylsilane (Et3SiH) or diisobutylaluminum hydride (DIBAL-H) as the reductant. The corresponding C-N hydrodeamination reaction is also briefly reported.

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.

Highly efficient aminocarbonylation of iodoarenes at atmospheric pressure catalyzed by a robust acenaphthoimidazolyidene allylic palladium complex

A robust allylic palladium-NHC complex was developed and exhibited extremely high catalytic activity toward aminocarbonylation of various (hetero)aryl iodides under atmospheric carbon monoxide pressure, in which a broad range of secondary and primary amines were well tolerated. In addition, the concise synthesis of an anticancer drug tamibarotene was accomplished even in a gram scale, further highlighting the practical applicability of the protocol.

Phosphonium chloride as a non-volatile chlorinating reagent: Preparation and reaction in no solvent or ionic liquid

Reaction of triphenylphosphine with trichloroisocyanuric acid in no solvent or an ionic liquid gave the corresponding phosphonium chloride, which can be used as a cheap and safe chlorinating reagent. Conversion of hydroxyheterocycles to chloroheterocycles, carboxylic acids to carboxylic acid chlorides, and primary amides to nitriles were accomplished by using the phosphonium chloride in excellent to good yields.

Cross coupling of acyl and aminyl radicals: Direct synthesis of amides catalyzed by Bu4NI with TBHP as an oxidant

A radical solution: A Bu4NI/tert-butyl hydroperoxide (TBHP) catalyzed synthesis of amides through a cross-coupling reaction between acyl and aminyl radicals is described. This method involves the combination of aldehyde C-H bond functionalization and decarbonylation of N,N-disubstituted formamides (see scheme). The cross-coupling is metal-free, has a wide substrate scope, operational simplicity, and gives high yields on scale-up. Copyright

A mild titanium-based system for the reduction of amides to aldehydes

A mild method for the reduction of amides to aldehydes using 1,1,3,3-tetramethyldisiloxane/titanium(IV) isopropoxide reducing system is described. The reaction occurs under mild conditions and allows the reduction of aromatic as well as aliphatic, tertiary amides to the corresponding aldehydes, in good yields. This methodology was extended to the reduction of aromatic secondary and primary amides to the corresponding aldehydes.