52803-59-5

Usage

Uses

Used in Pharmaceutical Industry:
2-[(4-CHLOROBENZYL)OXY]BENZALDEHYDE is used as an intermediate in the synthesis of various pharmaceuticals for its potential anti-inflammatory and anti-cancer properties. Its unique structure allows it to be a key component in the development of new drugs targeting specific health conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 2-[(4-CHLOROBENZYL)OXY]BENZALDEHYDE is utilized as a building block in the production of various agrochemicals. Its chemical properties make it suitable for the development of compounds that can be used in agriculture to improve crop yield and protect plants from pests.
Used in Fragrance and Flavor Industry:
2-[(4-CHLOROBENZYL)OXY]BENZALDEHYDE is used as an intermediate in the manufacturing of fragrances and flavors. Its aromatic properties contribute to the creation of unique scents and tastes for a variety of consumer products.
Used in Organic Chemistry as a Reagent:
In the field of organic chemistry, 2-[(4-CHLOROBENZYL)OXY]BENZALDEHYDE serves as a valuable chemical reagent. It aids in various chemical reactions and processes, facilitating the synthesis of complex organic compounds for research and industrial applications.

InChI:InChI=1/C14H11ClO2/c15-13-7-5-11(6-8-13)10-17-14-4-2-1-3-12(14)9-16/h1-9H,10H2

Upstream product

• 89-95-2 2-methyl-benzyl alcohol 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 90-02-8 salicylaldehyde 
• 622-95-7 4-chlorobenzyl bromide 

Downstream Products

• 39195-66-9 2-(4-chlorophenyl)benzofuran 
• 301348-23-2 C₁₇H₁₁ClN₂O 
• 1307886-78-7 1-(2-(4-chlorobenzyloxy)phenyl)hex-2-yn-1-one 
• 1307886-89-0 3-(4-chlorobenzyl)-2-propyl-4H-chromen-4-one 
• 1399846-23-1 2-(2-(4-chlorobenzyloxy)phenyl)-1-ethyl-1H-benzo[d]imidazole 
• 723247-07-2 C₁₆H₁₃ClO₃ 
• 1430841-86-3 2-(4-chlorobenzyloxy)benzaldehyde O-quinuclidin-3-yl oxime 
• 103311-43-9 4-[2-(4-Chloro-benzyloxy)-phenyl]-6-methyl-2-phenyl-1,4-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 103293-56-7 ethyl 4-[2-(4-chlorobenzyloxy)phenyl]-6-methyl-2-phenyl-5-pyrimidinecarboxylate 

Relevant academic research and scientific papers

Copper-Catalyzed Asymmetric Diyne Cyclization via [1,2]-Stevens-Type Rearrangement for the Synthesis of Chiral Chromeno[3,4-c]pyrroles

Here, we report a copper-catalyzed asymmetric cascade cyclization/[1,2]-Stevens-type rearrangement via a non-diazo approach, leading to the practical and atom-economic assembly of various valuable chiral chromeno[3,4-c]pyrroles bearing a quaternary carbon

Design, synthesis and biological evaluation of benzamide derivatives as novel NTCP inhibitors that induce apoptosis in HepG2 cells

Sodium taurocholate cotransport polypeptide (NTCP) plays an important role in the development of hepatitis and acts as a switch to allow hepatitis virus to enter hepatic cells. As the entry receptor protein of hepatitis virus, NTCP is also an effective ta

Design, synthesis and biological evaluation of benzyloxyphenyl-methylaminophenol derivatives as STAT3 signaling pathway inhibitors

STAT3 signaling pathway has been validated as a vital therapeutic target for cancer therapy. Based on the novel STAT3 inhibitor of a benzyloxyphenyl-methylaminophenol scaffold hit (1) discovered through virtual screening, a series of analogues had been designed and synthesized for more potent inhibitors. The preliminary SAR had been discussed and the unique binding site in SH2 domain was predicted by molecular docking. Among them, compounds 4a and 4b exhibited superior activities than hit compound (1) against IL-6/STAT3 signaling pathway with IC50 values as low as 7.71 μM and 1.38 μM, respectively. Compound 4a also displayed potent antiproliferative activity against MDA-MB-468 cell line with an IC50 value of 9.61 μM. We believe that these benzyloxyphenyl-methylaminophenol derivatives represent a unique mechanism for interrogating STAT3 as well as a potential structure type for further exploration.

Electrophilic carbon transfer in gold catalysis: Synthesis of substituted chromones

Using easily accessible aromatic alkoxy-arylalkynones, we have investigated the gold-catalyzed intramolecular addition of ethers to alkynes, to give easy access to various substituted chromones. This reaction involves the transfer of the ether substituent via a carbodemetallation process. We also noticed a competing isomerization of several starting materials for which we propose a second gold catalyzed mechanism.

Monosubstituted malononitriles: Efficient one-pot reductive alkylations of malononitrile with aromatic aldehydes

A powerful new one-pot method has been developed for the reductive alkylation of malononitrile with aromatic aldehydes. This new procedure has vastly improved the yield and efficiency of the process, and increased the scope of the aromatic aldehydes. Inco

CCR5 receptor antagonists: Discovery and SAR study of guanylhydrazone derivatives

High throughput screening (HTS) led to the identification of the guanylhydrazone of 2-(4-chlorobenzyloxy)-5-bromobenzaldehyde as a CCR5 receptor antagonist. Initial modifications of the guanylhydrazone series indicated that substitution of the benzyl group at the para-position was well tolerated. Substitution at the 5-position of the central phenyl ring was critical for potency. Replacement of the guanylhydrazone group led to the discovery of a novel series of CCR5 antagonists.

Synthesis and anticancer activity of benzyloxybenzaldehyde derivatives against HL-60 cells

A series of benzyloxybenzaldehyde derivatives were prepared and tested against the HL-60 cell line for anticancer activity. Preliminary structure-activity relationships were established. It was discovered that 2-(benzyloxy)benzaldehyde (17), 2-(benzyloxy)-4-methoxybenzaldehyde (26), 2-(benzyloxy)-5-methoxybenzaldehyde (27), 2-(benzyloxy)-5-chlorobenzaldehyde (28), 2-[(3-methoxybenzyl)oxy]benzaldehyde (29), 2-[(2-chlorobenzyl)oxy] benzaldehyde (30), and 2-[(4-chlorobenzyl)oxy]benzaldehyde (31) exhibited significant activity at 1-10 μM. Among them, compound 29 was the most potent one. The morphological assessment and DNA fragmentation analysis indicated that these compounds arrested cell cycle progression at G2/M phase and induced cell apoptosis. They resulted in the loss of mitochondrial membrane potential after 12 h of treatment.

Synthesis of heterocycles with MF/Al2O3 base-systems: 2-arylbenzofuranes and 2,3-diarylisoquinolin-1(2H)-ones

2-Benzyloxybenzaldehydes, -acetophenones and -benzophenones substituted in the benzyl part with electron-withdrawing groups, cyclize easily to 2-arylbenzofuranes by using a standardized KF- or CsF-Al2O3 base system. An efficient one-pot synthesis for 2,3-diarylisoquinolin-1(2H)-ones is possible by reacting a variety of arene carbaldehyde anils with phthalides under the same reaction conditions.