55082-33-2

Usage

Preparation

Preparation by Fries rearrangement of p-bromophenyl benzoate with aluminium chloride without solvent at 150° for 15 min (42%).

InChI:InChI=1/C13H9BrO2/c14-10-6-7-12(15)11(8-10)13(16)9-4-2-1-3-5-9/h1-8,15H

Upstream product

• 1523-17-7 4-bromophenyl benzoate 
• 117-99-7 2-Hydroxybenzophenone 
• 106-41-2 4-bromo-phenol 
• 98-07-7 Benzotrichlorid 
• 615-58-7 2,4-dibromophenol 
• 100-47-0 benzonitrile 
• 2476-35-9 5-bromo-2-methoxybenzoic acid 
• 65-85-0 benzoic acid 
• 591-50-4 iodobenzene 
• 1761-61-1 5-bromosalicyclaldehyde 
• 108-86-1 bromobenzene 
• 98-80-6 phenylboronic acid 
• 90-02-8 salicylaldehyde 
• 501-65-5 diphenyl acetylene 

Downstream Products

• 69918-18-9 (E)-(5-bromo-2-hydroxyphenyl)(phenyl)methanone oxime 
• 84437-30-9 3-benzoyl-4-hydroxybenzonitrile 
• 324061-77-0 4-bromo-2-(hydroxy(phenyl)methyl)phenol 
• 1225592-31-3 (2-benzoyl-4-bromophenoxy)acetonitrile 
• 1295567-90-6 4-bromo-2-{α-[1-(4-bromophenyl)benzoimidazol-2-yl]benzyl}phenol 
• 1295567-91-7 4-bromo-2-{α-[1-(4-dimethylaminophenyl)benzoimidazol-2-yl]benzyl}phenol 
• 1295567-92-8 C₂₆H₁₉BrN₂O 
• 1295567-93-9 C₂₄H₁₇BrN₂O₂ 
• 1295567-94-0 4-bromo-2-{α-[1-(2-thienyl)benzoimidazol-2-yl]-benzyl}phenol 
• 1295567-95-1 C₂₆H₁₈BrN₃O₃ 
• 180861-07-8 2-[(2-aminophenylimino)phenylmethyl]-4-bromophenol 
• 1014718-67-2 JBL-43 
• 1007862-27-2 2-(amino(phenyl)methyl)-4-bromophenol 

Relevant academic research and scientific papers

Aerobic Copper-Catalyzed Salicylaldehydic Cformyl?H Arylations with Arylboronic Acids

We report a challenging copper-catalyzed Cformyl?H arylation of salicylaldehydes with arylboronic acids that involves unique salicylaldehydic copper species that differ from reported salicylaldehydic rhodacycles and palladacycles. This protocol has high chemoselectivity for the Cformyl?H bond compared to the phenolic O?H bond involving copper catalysis under high reaction temperatures. This approach is compatible with a wide range of salicylaldehyde and arylboronic acid substrates, including estrone and carbazole derivatives, which leads to the corresponding arylation products. Mechanistic studies show that the 2-hydroxy group of the salicylaldehyde substrate triggers the formation of salicylaldehydic copper complexes through a CuI/CuII/CuIII catalytic cycle.

Discovery of long-chain salicylketoxime derivatives as monoacylglycerol lipase (MAGL) inhibitors

Monoacylglycerol lipase (MAGL) is the enzyme hydrolyzing the endocannabinoid 2-arachidonoylglycerol (2-AG) to free arachidonic acid and glycerol. Therefore, MAGL is implicated in many physiological processes involving the regulation of the endocannabinoid system and eicosanoid network. MAGL inhibition represents a potential therapeutic target for many diseases, including cancer. Nowadays, most MAGL inhibitors inhibit this enzyme by an irreversible mechanism of action, potentially leading to unwanted side effects from chronic treatment. Herein, we report the discovery of long-chain salicylketoxime derivatives as potent and reversible MAGL inhibitors. The compounds herein described are characterized by a good target selectivity for MAGL and by antiproliferative activities against a series of cancer cell lines. Finally, modeling studies suggest a reasonable hypothetical binding mode for this class of compounds.

Series of high spin mononuclear iron(III) complexes with Schiff base ligands derived from 2-hydroxybenzophenones

The reaction of various phenols with benzoyl chloride afforded the derivatives of phenyl benzoate that subsequently underwent Fries rearrangement. The obtained 2-hydroxybenzophenone analogues were combined with linear aliphatic triamines, which afforded pentadentate Schiff base ligands. Moreover, nine new iron(iii) complexes with the general formula [Fe(Ln)X] (where, Ln is the dianion of the pentadentate Schiff base ligand, N,N′-bis((2-hydroxy-5-methylphenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L1, N,N′-bis((2-hydroxy-3,5-dimethylphenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L2, N,N′-bis((2-hydroxy-5-chlorophenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L3, N,N′-bis((2-hydroxy-4-methylphenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L4, N,N′-bis((2-hydroxy-5-bromophenyl)phenyl)methylidene-1,7-diamino-4-azaheptane = H2L5, N,N′-bis((2-hydroxy-5-bromophenyl)phenyl)methylidene-1,7-diamino-4-methyl-4-azaheptane = H2L6 and X is the chlorido, azido or isocyanato terminal ligand) were synthesized and characterized via elemental analysis, and IR and UV-VIS spectroscopy; in addition, the crystal structures of all the complexes were determined by X-ray diffraction. Magnetic investigation reveals high spin state behaviour in all the reported compounds. DFT calculations and analysis of the magnetic functions allowed to extract absolute values of the zero field splitting parameters and exchange coupling constants.

Acid-Functionalised Magnetic Ionic Liquid [AcMIm]FeCl4 as Catalyst for Oxidative Hydroxylation of Arylboronic Acids and Regioselective Friedel–Crafts Acylation

An acid-functionalised, magnetic, room-temperature ionic liquid, 1-acyl-3-methylimidazolium tetrachloroferrate ([AcMIm]FeCl4), was synthesised and its optical, magnetic, and thermal properties were investigated. The magnetic moment (0.05402 emu in 2 T magnetic fields) showed strong paramagnetic behaviour, and thermogravimetric analysis indicated very good thermal stability with a decomposition temperature higher than 230 °C. Additionally, [AcMIm]FeCl4 efficiently catalysed the oxidative ipso-hydroxylation of arylboronic acids and regioselective Friedel–Crafts acylation without external organic solvent or additives, such as acids, base, and ligands. This functionalised ionic liquid, [AcMIm]FeCl4, was recycled and reused at least six times without significant loss of its catalytic properties and stability.

Acylation of Csp2-H bond with acyl sources derived from alkynes: Rh-Cu bimetallic catalyzed CC bond cleavage

A Rh-Cu bimetallic catalyzed o-acylation of acyloxacetamide with alkynes has been described. This transformation provides a novel, concise way to synthesize ortho-acylphenols using functionalized alkynes as acylating reagents. Mechanistic studies revealed a Rh-Cu relay process, in which O2 plays a critical role for the formation of carbonyl compounds.

PdCl2/DABCO-catalyzed direct arylation of 2-hydroxybenzaldehydes in H2O

In this paper the successful application of DABCO both as base and as ligand for efficient coupling reactions of aryl iodides and bromides with 2-hydroxybenzaldehydes in the presence of catalytic amounts of PdCl2 in water as solvent was introduced.

Rh(III)-catalyzed aldehyde C-H bond functionalization of salicylaldehydes with arylboronic acids

A Rh(III)-catalyzed aldehyde C-H bond functionalization of salicylaldehydes with arylboronic acids has been developed, with features of mild reaction condition and high efficiency. Furthermore, the functionalized 2-hydroxybenzophenone could be subject to divergent synthesis of heterocycles.

Chemoselective C-benzoylation of phenols by using ALCl3under solvent-free conditions

Substituted phenols were chemo-selectively reacted with benzoylchloride in presence of aluminum chloride under solvent-free condition to afford the corresponding 2′-hydroxy aryl benzophenones in excellent yields (72-96%). Naphthol benzoylation resulted in lower yields as compared to phenols. Both reactions completed in 5-10 min with quantitative yields providing excellent control over regioselectivity of products.

Palladium-catalyzed direct C-H arylation of 2-hydroxybenzaldehydes with organic halides in neat water

The palladium-catalyzed cross-coupling of 2-hydroxybenzaldehydes with organic halides proceeds in the presence of n-Bu4NBr in H2O producing the corresponding 2-hydroxybenzophenones in high yields.

First direct access to 2-hydroxybenzophenones via nickel-catalyzed cross-coupling of 2-hydroxybenzaldehydes with aryl iodides

An efficient, inexpensive and reusable NiCl2·6H2O/n-Bu4NBr catalytic system is described for the direct C-H arylation of 2-hydroxybenzaldehydes with aryl iodides for the first time.