5176-12-5

Usage

Uses

Used in Pharmaceutical Industry:
(2-NITRO-PHENYL)-PHENYL-METHANOL is used as an intermediate in the synthesis of pharmaceuticals for its potential applications in the development of new drugs.
Used in Organic Chemistry:
(2-NITRO-PHENYL)-PHENYL-METHANOL is used as a building block in the synthesis of various organic compounds due to its unique structural and chemical properties.
It is important to handle and use this chemical with caution, following proper safety measures and regulations, as it may have potential hazards and risks associated with its use.

InChI:InChI=1/C13H11NO3/c15-13(10-6-2-1-3-7-10)11-8-4-5-9-12(11)14(16)17/h1-9,13,15H

Upstream product

• 552-89-6 2-nitro-benzaldehyde 
• 108-86-1 bromobenzene 
• 100-58-3 phenylmagnesium bromide 
• 98-80-6 phenylboronic acid 
• 934-56-5 trimethyl(phenyl)stannane 
• 609-73-4 o-nitroiodobenzene 
• 100-52-7 benzaldehyde 
• 76847-20-6 2-Nitro-1-benzol 

Downstream Products

• 132886-33-0 (+/-)-succinic acid mono-(2-nitro-benzhydryl ester) 
• 114305-23-6 (+/-)-phthalic acid mono-(2-nitro-benzhydryl ester) 
• 6502-35-8 o-nitrosobenzophenone 
• 76847-20-6 2-Nitro-1-benzol 
• 13260-76-9 4-phenyl-1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one 
• 2243-79-0 2-nitrobenzophenone 
• 179104-54-2 1-(methoxy(phenyl)methyl)-2-nitrobenzene 
• 108621-64-3 acetic acid (2-nitro-phenyl)-phenyl-methyl ester 
• 479637-60-0 dichloro-acetic acid (2-nitro-phenyl)-phenyl-methyl ester 
• 479637-59-7 chloro-acetic acid (2-nitro-phenyl)-phenyl-methyl ester 
• 479637-61-1 trichloro-acetic acid (2-nitro-phenyl)-phenyl-methyl ester 
• 13097-01-3 3-phenyl-1H-indazole 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 540750-66-1 2-nitrobenzophenone oxime 

Relevant academic research and scientific papers

Photo-Induced N-N Coupling of o-Nitrobenzyl Alcohols and Indolines to Give N-Aryl-1-amino Indoles

A novel method to synthesize N-aryl-1-amino indoles was established by the photoinduced N-N coupling reaction. This protocol is by treatment of o-nitrobenzyl alcohols and indolines in the presence of TEAI and acetic acid with a 24 W ultraviolet (UV) light

Release of Terminal Alkynes via Tandem Photodeprotection and Decarboxylation of o -Nitrobenzyl Arylpropiolates in a Flow Microchannel Reactor

Photocleavable protecting groups (PPGs) offer a complementary protection paradigm compared to traditional protection groups. Herein, an o-nitrobenzyl (NB) PPG was employed to protect a variety of arylpropiolic acids. Upon a cascade of light-triggered photodeprotection in a microchannel reactor (residence times of 100-500 s), followed by Cu-catalyzed decarboxylation at 60 °C, the NB-protected arylpropiolic acid afforded a terminal alkyne. This terminal alkyne was further reacted in situ with an azide via click chemistry to yield a 1,2,3-triazole in a one-pot reaction. Furthermore, the effect of different substituents (methyl, vinyl, allyl, and phenyl) at the benzylic position on the rate of photodeprotection was studied. The quantum yields of photolysis for the benzylic-substituted esters were determined to be as high as 0.45 compared to the unsubstituted ester with a 0.08 quantum yield of photolysis.

Intramolecular addition of diarylmethanols to imines promoted by KO: T -Bu/DMF: A new synthetic approach to indole derivatives

KOt-Bu/DMF promoted intramolecular addition of diarylmethanols to imines was developed. A series of 2,3-disubstituted indoles was obtained in good yields. A reaction mechanism of radical cyclization and subsequent dehydration is proposed.

From in vitro to in cellulo: Structure-activity relationship of (2-nitrophenyl)methanol derivatives as inhibitors of PqsD in Pseudomonas aeruginosa

Recent studies have shown that compounds based on a (2-nitrophenyl)methanol scaffold are promising inhibitors of PqsD, a key enzyme of signal molecule biosynthesis in the cell-to-cell communication of Pseudomonas aeruginosa. The most promising molecule displayed anti-biofilm activity and a tight-binding mode of action. Herein, we report on the convenient synthesis and biochemical evaluation of a comprehensive series of (2-nitrophenyl)methanol derivatives. The in vitro potency of these inhibitors against recombinant PqsD as well as the effect of selected compounds on the production of the signal molecules HHQ and PQS in P. aeruginosa were examined. The gathered data allowed the establishment of a structure-activity relationship, which was used to design fluorescent inhibitors, and finally, led to the discovery of (2-nitrophenyl)methanol derivatives with improved in cellulo efficacy providing new perspectives towards the application of PqsD inhibitors as anti-infectives. This journal is the Partner Organisations 2014.

Validation of PqsD as an anti-biofilm target in pseudomonas aeruginosa by development of small-molecule inhibitors

2-Heptyl-4-hydroxyquinoline (HHQ) and Pseudomonas quinolone signal (PQS) are involved in the regulation of virulence factor production and biofilm formation in Pseudomonas aeruginosa. PqsD is a key enzyme in the biosynthesis of these signal molecules. Using a ligand-based approach, we have identified the first class of PqsD inhibitors. Simplification and rigidization led to fragments with high ligand efficiencies. These small molecules repress HHQ and PQS production and biofilm formation in P. aeruginosa. This validates PqsD as a target for the development of anti-infectives.

Nitro-substituted aryl lithium compounds in microreactor synthesis: Switch between kinetic and thermodynamic control

Be quick or take your time, depending on your goal: A microflow method for the generation and transformation of o-, m-, and p-nitro-substituted aryl lithium compounds enabled the selective use of either the kinetically or the thermodynamically preferred intermediate. In the example pictured, a residence time of 0.06 s at -48 °C led to the formation of 1, whereas 2 was obtained exclusively when the residence time was extended to 63 s.

Highly efficient and facile aryl transfer to aldehydes using ArB(OH) 2-GaMe3

A rapid and efficient procedure for the synthesis of diarylmethanols has successfully been achieved by the aryl transfer to aldehydes using the ArB(OH)2-GaMe3 combined systems in excellent yields (up to 98%) at room temperature. Georg Thieme Verlag Stuttgart.

Copper(II) acetate-catalyzed addition of arylboronic acids to aromatic aldehydes

A novel copper-catalyzed protocol for the synthesis of carbinol derivatives has been developed. In the presence of copper(II) acetate and dppf, carbinol derivatives were prepared by the addition of arylboronic acids to aromatic aldehydes in good to excellent yields. Moreover, the rigorous exclusion of air or moisture is not required in these transformations.

Cascade synthesis of 3-quinolinecarboxylic ester via benzylation/ propargylation-cyclization

(Chemical Equation Presented) Reactions of 2-amino-aryl alcohols with β-ketoesters catalyzed by a catalytic amout of FeCl3 via tandem benzylation-cyclization produce the corresponding 3-quinolinecarboxylic esters in good to high yields. Extending this methodology to propargylation- cyclization, 2-nitrophenyl propargyl alcohols with β-ketoesters catalyzed by FeCl3 and SnCl2 also produce the 4-alkyne-3- quinolinecarboxylic esters. The mechanistic details of this benzylation/ propargylation and cyclization cascade process are also discussed.

Palladium-catalyzed 1,2-addition of potassium aryl- and alkenyltrifluoroborates to aldehydes using thioether-imidazolinium carbene ligands

(Chemical Equation Presented) Palladium-catalyzed 1,2-addition of potassium aryl- and alkenyltrifluoroborates to aldehydes using thioether- imidazolinium carbene ligands proceeded readily under aqueous conditions. This process tolerated a diverse range of potassium trifluoroborate salts and aldehydes, giving a variety of carbinol derivatives with good to excellent yields.