2734-77-2

Basic information

• Product Name: 2,4-dinitrophenyl naphthalen-2-yl ether
• Synonyms: 2-(2,4-Dinitrophenoxy)naphthalene; 2-(2,4-Dinitro-phenoxy)-naphthalene; 2,4-Dinitrophenyl 2-naphthyl ether; naphthalene, 2-(2,4-dinitrophenoxy)-
• CAS NO: 2734-77-2
• Molecular Formula: C₁₆H₁₀N₂O₅
• Molecular Weight: 310.261
• Mol File: 2734-77-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 455.1°C at 760 mmHg
• Flash Point: 196.6°C
• Density: 1.424g/cm³
• Vapor Pressure: 4.88E-08mmHg at 25°C
• Refractive Index: 1.694
• CAS DataBase Reference: 2,4-dinitrophenyl naphthalen-2-yl ether(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dinitrophenyl naphthalen-2-yl ether(2734-77-2)
• EPA Substance Registry System: 2,4-dinitrophenyl naphthalen-2-yl ether(2734-77-2)

Safety Data

• Hazardous Substances Data: 2734-77-2(Hazardous Substances Data)

Usage

General Description

2,4-dinitrophenyl naphthalen-2-yl ether is a chemical compound that is used in organic synthesis and research. It is also known as Picrylnaphthol and has the molecular formula C16H9N3O6. 2,4-dinitrophenyl naphthalen-2-yl ether is a yellow crystalline solid with a high melting point and is insoluble in water. It is commonly used as a reagent for the determination of aldehydes and ketones in organic chemistry. As a strong nucleophile, it is also used in organic reactions to form new chemical compounds. The compound has potential applications in medicinal chemistry, as well as in the manufacturing of dyes and pigments. However, it is important to handle this compound with care due to its potential health hazards.

Upstream product

• 62790-91-4 2-(dimethyl-1,1’-dimethylethylsilyloxy)naphthalene 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 15147-55-4 2-naphtholate 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 67-56-1 methanol 
• 36294-21-0 potassium 2-naphthoxide 
• 135-19-3 β-naphthol 
• 875-83-2 sodium 2-naphtholate 
• 584-48-5 2,4-dinitrobromobenzene 

Downstream Products

• 961-68-2 N-phenyl-2,4-dinitroaniline 
• 135-19-3 β-naphthol 
• 13059-86-4 2,4-dinitro-N-butylaniline 
• 119-27-7 2,4-dinitroanisole 

Relevant articles and documents

Chemical validation of a druggable site on Hsp27/HSPB1 using in silico solvent mapping and biophysical methods

Destabilizing mutations in small heat shock proteins (sHsps) are linked to multiple diseases; however, sHsps are conformationally dynamic, lack enzymatic function and have no endogenous chemical ligands. These factors render sHsps as classically “undruggable” targets and make it particularly challenging to identify molecules that might bind and stabilize them. To explore potential solutions, we designed a multi-pronged screening workflow involving a combination of computational and biophysical ligand-discovery platforms. Using the core domain of the sHsp family member Hsp27/HSPB1 (Hsp27c) as a target, we applied mixed solvent molecular dynamics (MixMD) to predict three possible binding sites, which we confirmed using NMR-based solvent mapping. Using this knowledge, we then used NMR spectroscopy to carry out a fragment-based drug discovery (FBDD) screen, ultimately identifying two fragments that bind to one of these sites. A medicinal chemistry effort improved the affinity of one fragment by ~50-fold (16 μM), while maintaining good ligand efficiency (~0.32 kcal/mol/non-hydrogen atom). Finally, we found that binding to this site partially restored the stability of disease-associated Hsp27 variants, in a redox-dependent manner. Together, these experiments suggest a new and unexpected binding site on Hsp27, which might be exploited to build chemical probes.

DBU-mediated mild and chemoselective deprotection of aryl silyl ethers and tandem biaryl ether formation

An efficient method for the selective cleavage of aryl silyl ethers is established using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). With either 1.0 or 0.10 equivalent of DBU, smooth desilylation of various aryl silyl ethers was accomplished selectively in the presence of alkyl silyl ethers and other base-sensitive groups such as acetate and ester. In addition, direct transformation of aryl silyl ethers into biaryl ethers using a catalytic amount of DBU was possible through tandem desilylation and SNAr reaction with activated aryl fluorides. Georg Thieme Verlag Stuttgart.

Rapid synthesis of nitro substituted diaryl ethers under mild conditions

Various nitro substituted diaryl ethers have been synthesized rapidly by using polymer supported phenoxide anions and halides under mild conditions. The isolation of pure products by simple filtration and evaporation is an important feature of this method.