4397-53-9

Usage

Uses

Used in Pharmaceutical Industry:
4-Benzyloxybenzaldehyde is used as an intermediate in the synthesis of various pharmaceutical compounds. One such example is the synthesis of (5-fluoro-(2R,3S)-2,3-bis(4-hydroxyphenyl)pentanenitrile), an estrogen receptor β-selective ligand. 4-Benzyloxybenzaldehyde has potential applications in the development of drugs targeting estrogen receptor-related diseases.
Used in Cancer Research:
Although 4-Benzyloxybenzaldehyde has much less potent anticancer activity against HL-60 cells compared to its isomer, it still holds potential for cancer research. Further studies and modifications to its structure may lead to the development of more effective anticancer agents.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 32, p. 192, 1989 DOI: 10.1021/jm00121a035

InChI:InChI=1/C14H12O2/c15-10-12-6-8-14(9-7-12)16-11-13-4-2-1-3-5-13/h1-10H,11H2

Upstream product

• 100-39-0 benzyl bromide 
• 123-08-0 4-hydroxy-benzaldehyde 
• 100-44-7 benzyl chloride 
• 836-43-1 4-benzyloxybenzyl alcohol 
• 74994-62-0 4-(benzyloxy)-3-iodobenzaldehyde 
• 188038-47-3 3'-[4-(phenylmethoxy)phenyl][5,6]fullereno-C₆₀-I_h-[1,9-d]isoxazole 
• 39236-04-9 2-(4-(benzyloxy)phenyl)-1,3-dithiane 
• 100-51-6 benzyl alcohol 
• 58765-11-0 4-hydroxybenzaldehyde potassium salt 
• 58327-40-5 α-Hydroxy-4-(phenylmethoxy)benzeneacetonitrile 
• 6547-53-1 2-[4-(benzyloxy)benzyl]acetic acid 
• 76193-67-4 4-benzyloxybenzaldehyde oxime 
• 140174-89-6 (2S)-2-N-Boc-amino-3-(4-benzyloxyphenyl)propyl acetate 
• 205578-45-6 9-(4-Benzyloxy-benzyl)-9H-carbazole 

Downstream Products

• 73839-66-4 α-(4-Benzyloxybenzyliden)-butyrolacton 
• 84002-48-2 (E)-1-(4-(benzyloxy)-2-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one 
• 111391-35-6 (E)-3-(4-(benzyloxy)phenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one 
• 19158-99-7 (E)-3-(4-(benzyloxy)phenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 
• 2982-55-0 1-benzyloxy-4-(2-nitroethenyl)benzene 
• 2982-55-0 (E)-1-(benzyloxy)-4-(2-nitrovinyl)benzene 
• 114160-09-7 3t-(4-benzyloxy-phenyl)-1-(1-hydroxy-[2]naphthyl)-propenone 
• 111391-33-4 4-benzyloxy-2'-hydroxy-6'-methoxy-trans-chalcone 
• 103050-95-9 3t-(4-benzyloxy-phenyl)-1-(4-bromo-1-hydroxy-[2]naphthyl)-propenone 
• 836-43-1 4-benzyloxybenzyl alcohol 
• 76193-67-4 4-benzyloxybenzaldehyde oxime 
• 652539-35-0 7,4'-dibenzyloxy-2-styrylchromone 
• 111391-32-3 (E)-3-(4-(benzyloxy)phenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 86711-45-7 (E)-3-(4-(benzyloxy)phenyl)-1-(p-tolyl)prop-2-en-1-one 

Relevant academic research and scientific papers

Coordination chemistry of [methyl-3-(4-benzyloxyphenyl)methylene] dithiocarbazate with divalent metal ions: Crystal structures of the N,S Schiff base and of its bis-chelated nickel(II) complex

The condensation of 4-benzyloxybenzaldehyde with S-methyldithiocarbazate (SMDTC) yielded the Schiff base methyl-3-[(4-benzyloxyphenyl)methylene] dithiocarbazate (HL) that, upon reaction with different metal ions, afforded bis-chelated complexes, ML2

Synthesis and pharmacological evaluation of pyrazole derivatives containing sulfonamide moiety

A new series of N-[4-[N-[4-[5-[4-(benzyloxy)phenyl]-1-(substituted phenyl)-1H-pyrazol-3-yl]phenyl]sulfamoyl]phenyl]acetamide derivatives were synthesized and elucidated by spectral data. All the compounds were subjected to in vitro evaluation for anti-inflammatory (BSA anti-denaturation assay), antioxidant (DPPH radical scavenging assay) and in vivo screening for anti-inflammatory (carrageenan induced rat paw edema inhibition)?activities. Selected active compounds were evaluated for ulcerogenic, lipid peroxidation, and LPS induced TNF-α production inhibition potential. The most active compound in the series showed an in vivo anti-inflammatory efficacy of 83.1?% when compared to diclofenac sodium (81.6?%). Evaluation of ulcer index and biochemical estimation for oxidative stress also revealed that this compound was safe on gastric mucosa and did not induce oxidative stress in tissues. When further tested for LPS induced TNF-α production inhibition in mice, it showed a better inhibition (ID50?=?6.23?mg/kg) when compared to standard inhibitor, SB 203580 (ID50?=?28.40?mg/kg). The p38α MAP kinase docking score of this active compound was also found to be better than that of SB 203580. Graphical abstract: [Figure not available: see fulltext.]

Decatungstate Catalyzed Synthesis of Trifluoromethylthioesters from Aldehydes via a Radical Process

Here we report a mild and general method for the trifluoromethylthiolation of aldehydes using N-trifluoromethylthiosaccharin as the CF3S radical source and sodium decatungstate (NaDT) as the photocatalyst. This reaction proceeds via hydrogen at

NaI-mediated oxidative amidation of benzyl alcohols/aromatic aldehydes to benzamides via electrochemical reaction

In this research, we have developed a mild electrochemical process for oxidative amidation of benzyl alcohols/aromatic aldehydes with cyclic amines into the corresponding benzamides. This electroorganic synthetic method proceeds using NaI as a redox mediator under ambient temperature in undivided cell, providing more than 25 examples of amide products in moderate to good yields. The benefits of this reaction include one-pot synthesis, open air condition, proceed in aqueous media and no requirement of external conducting salt, base and oxidant.

Total synthesis and biological evaluation of 7-hydroxyneolamellarin A as hypoxia-inducible factor-1α inhibitor for cancer therapy

7-Hydroxyneolamellarin A (7-OH-Neo A, 1), a natural marine product derived from sponge Dendrilla nigra, was first synthesized with 10% overall yield under the instruction of convergent synthetic strategy. We found that 7-OH-Neo A could attenuate the accum

Catalytic δ-hydroxyalkynone rearrangement in the stereoselective total synthesis of centrolobine, engelheptanoxides A and C and analogues

A catalytic stereoselective total synthesis of centrolobine and engelheptanoxides A and C has been completed via a metal-free catalytic δ-hydroxyalkynone rearrangement to 2,3-dihydro-4H-pyran-4-one and diastereoselective hydrogenation to the all syn-2,4,6-trisubstituted pyran strategy. The onliest required chirality was introduced by Jacobsen kinetic resolution, which further directed the diastereoselective hydrogenation. A first stereoselective synthesis of engelheptanoxide A is also accomplished. The analogues and derivatives of centrolobine and engelheptanoxides prepared were evaluated for antitubercular activity against M. tuberculosis H37Rv ATCC 27294.

Method for preparing novel crystalline forms of 1-(4-benzyloxy-benzyl)-3-methyl-thiourea

The present disclosure relates to a method for preparing 1-(4-benzyloxy-benzyl)-3-methyl-thiourea and a method for preparing a novel stable crystalline form A of 1-(4-benzyloxy-benzyl)-3-methyl-thiourea.

Stereostructure Clarifying Total Synthesis of the (Polyenoyl)tetramic Acid Militarinone B. A Highly Acid-Labile N-Protecting Group for Amides ?

The 5S, 8′R, and 10′R configurations of militarinone B (3), which is a natural product from Paecilomyces militaris, should equal those in its biosynthetic precursor, militarinone C. The configuration at C-1′ emerged from syntheses of the militarinone B candidates 1′′S- and 1′′R-(5S,8′R,10′R)-3 from the building blocks 9, 11, 14, and 15a while introducing TMB as a more acid-labile N-protecting group for β-ketoamides than DMB. Comparisons of 1′′S- and 1′′R-(5S,8′R,10′R)-3 with natural militarinone B (3; reisolated from Nature) revealed identity versus distinctness.

Chromium-Salen Complex/Nitroxyl Radical Cooperative Catalysis: A Combination for Aerobic Intramolecular Dearomative Coupling of Phenols

We describe an aerobic intramolecular dearomative coupling reaction of tethered phenols using a catalytic system consisting of a chromium-salen (Cr-salen) complex combined with a nitroxyl radical. This novel catalytic system enables formation of various spirocyclic dienone products including those unable to be accessed by previously reported methods efficiently under mild reaction conditions.

Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction

A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.