78725-72-1

Usage

Classification

Organic compound belonging to the class of benzene and substituted derivatives

Chemical properties

Contains a nitro group, an ethynyl group, and a hydroxyl group

Uses

Organic synthesis and pharmaceutical research

Safety precautions

Handle with care to avoid skin and eye irritation, respiratory tract irritation, and central nervous system impacts

Potential uses

Solvent for reactions, starting material for synthesis of other organic compounds

Upstream product

• 552-89-6 2-nitro-benzaldehyde 
• 4301-14-8 acetylenemagnesium bromide 

Downstream Products

• 127559-57-3 1-(2-nitrophenyl)-2,3-butadien-1-ol 
• 1437326-14-1 C₂₂H₁₈N₄O₄ 
• 1437326-13-0 C₂₁H₁₆N₄O₄ 
• 1437326-12-9 C₂₁H₁₆N₄O₃ 
• 1437326-11-8 C₁₉H₂₀N₄O₃ 
• 1437326-10-7 C₁₅H₁₂N₄O₃ 
• 1437326-09-4 C₁₆H₁₁F₃N₄O₃ 
• 1437326-08-3 C₁₆H₁₄N₄O₃ 
• 1437326-07-2 C₁₇H₁₆N₄O₃ 
• 1437326-06-1 C₁₈H₁₈N₄O₃ 
• 1437326-05-0 C₁₈H₁₈N₄O₃ 
• 1437325-97-7 C₁₈H₁₈N₄O₃ 
• 1437325-72-8 (2-aminophenyl)(1-(3-ethylphenyl)-1H-1,2,3-triazol-4-yl)methanone 
• 1437325-71-7 (2-aminophenyl)(1-(3-isopropylphenyl)-1H-1,2,3-triazol-4-yl)methanone 

Relevant academic research and scientific papers

Drastic fluorine effect: Complete reversal of the selectivity in the Au-catalyzed hydroalkoxylation reaction of fluorinated haloalkynes

The gold-catalyzed hydration reaction of haloalkynes is highly regioselective producing 2-halomethylketones as the sole products. Herein, we document a drastic fluorine effect where the reaction of 1-halo-3,3-difluoroalkynes as substrates leads to a complete reversal of selectivity and produces 3,3-difluoroesters as the unique products.

Ligand-Controlled Palladium-Catalyzed Carbonylation of Alkynols: Highly Selective Synthesis of α-Methylene-β-Lactones

The first general and regioselective Pd-catalyzed cyclocarbonylation to give α-methylene-β-lactones is reported. Key to the success for this process is the use of a specific sterically demanding phosphine ligand based on N-arylated imidazole (L11) in the presence of Pd(MeCN)2Cl2 as pre-catalyst. A variety of easily available alkynols provide under additive-free conditions the corresponding α-methylene-β-lactones in moderate to good yields with excellent regio- and diastereoselectivity. The applicability of this novel methodology is showcased by the direct carbonylation of biologically active molecules including natural products.

Pd/C-catalyzed synthesis of (E)-2-arylmethylideneindolin-3-ols under ultrasound: Their initial evaluation as potential anti-proliferative agents

(E)-2-Arylmethylideneindolin-3-ol derivatives have been explored as new and potential anti-proliferative agents. Synthesis of these compounds was carried out by using a Pd/C-catalyzed alternative and one-pot method involving C-C coupling of 1-(2-(p-tosylamino)phenyl)prop-2-yn-1-ol with a range of iodoarenes followed by intramolecular hydroamination in the same pot. The reaction proceeded faster when performed under ultrasound irradiation. All these compounds showed selective growth inhibition of MDA-MB 231 cancer cells

1-Phenyl-4-benzoyl-1H-1,2,3-triazoles as orally bioavailable transcriptional function suppressors of Estrogen-related receptor α

Estrogen-related receptor α is a potential candidate target for therapeutic treatment of breast cancer. We describe the discovery and structure-activity relationship study of a series of 1-phenyl-4-benzoyl-1H-1,2, 3-triazoles as novel suppressors of ERRα

Palladium-catalyzed approach for the general synthesis of (E)-2-arylmethylidene-N-tosylindolines and (E)-2-arylmethylidene-N-tosyl/ nosyltetrahydroquinolines: Access to 2-substituted indoles and quinolines

A facile and efficient method for the synthesis of (E)-2-arylmethylidene-N- tosylindolines and (E)-2-arylmethylidene-N-tosyl/nosyltetrahydroquinoline variants has been developed through palladium-catalyzed cyclocondensation of aryl iodides with readily available 1-(2-tosylaminophenyl)prop-2-yn-1-ols and their higher homologues, respectively. The proposed reaction mechanism invokes the operation of trans-aminopalladation during cyclization (5/6-exo-dig), which ensures exclusive (E)-stereochemistry in the products. The method is fast, operationally simple, totally regio- and stereoselective, and versatile enough to access a variety of 2-substituted indoles and quinolines. The reactions proceeded efficiently with a wide variety of substrates and afforded the corresponding products in moderate to excellent yields.

Modular synthesis of photocleavable peptides using click chemistry

A modular synthesis of photocleavable peptides was developed. Peptide based kinase substrates were modified on solid support with a traceless linker derived from 1-(2-nitrophenyl)propargyl alcohol and coupled to azide functionalized cell-penetrating pepti

Syntheses and synthetic applications of stannylated allylic alcohols

Allenyl carbinols undergo regioselective hydrostannation in the presence of MoBl3, a catalyst originally developed for the hydrostannation of alkynes, giving rise to allyl stannanes. These allyl stannanes can easily be converted into useful synthetic building blocks such as allyl iodides or vinyl epoxides.

Improved ethynylation of nitrocarbonyl derivatives by cerium trichloride assisted addition of ethynyl magnesium bromide

The addition of the Grignard reagent ethynyl magnesium bromide to nitroarylcarbonyls in the presence of cerium chloride was investigated. Thus, 2- and 4-nitrobenzaldehyde, 2- and 4-nitroacetophenone, 2-nitrocinnamaldehyde and 1-aryl-3-aryl′-2-en-propanones (nitrochalcones 4a-g), gave α-ethynyl-2- and 4-nitrophenylmethanol 2a-b, α-ethynyl-2- and 4-nitrophenyl ethanol 2c-d, trans-1-(2-nitrophenyl)-1-penten-4-yn-3-ol (5) and trans-1-aryl-3-aryl′-1-penten-4-yn-3-ol 6a-g, respectively. It was found that in the absence of the lanthanide, the ethynylation reaction was a low yielding process. WILEY-VCH Verlag GmbH, 1999.