53389-99-4

Basic information

• Product Name: 2-(2-CHLOROBENZYLOXY)BENZALDEHYDE
• Synonyms: ASISCHEM N43070;AURORA 23254;2-(2-CHLOROBENZYLOXY)BENZALDEHYDE;AKOS B005838;OTAVA-BB BB7110952582;ZERENEX E/4048043
• CAS NO: 53389-99-4
• Molecular Formula: C₁₄H₁₁ClO₂
• Molecular Weight: 246.69
• Mol File: 53389-99-4.mol

Chemical Properties

• Melting Point: 84 °C
• Boiling Point: 387.3 °C at 760 mmHg
• Flash Point: 161.2 °C
• Appearance: /
• Density: 1.247 g/cm³
• Vapor Pressure: 3.34E-06mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: 2-(2-CHLOROBENZYLOXY)BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-CHLOROBENZYLOXY)BENZALDEHYDE(53389-99-4)
• EPA Substance Registry System: 2-(2-CHLOROBENZYLOXY)BENZALDEHYDE(53389-99-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 53389-99-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(2-CHLOROBENZYLOXY)BENZALDEHYDE is used as a building block for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Dye Production:
In the dye industry, 2-(2-CHLOROBENZYLOXY)BENZALDEHYDE is utilized for the production of dyes. Its aromatic nature and chemical reactivity make it suitable for creating a range of colorants used in various applications.
Used in Polymer Synthesis:
2-(2-CHLOROBENZYLOXY)BENZALDEHYDE is also employed in the synthesis of polymers. Its chemical structure can be incorporated into polymer chains to modify their properties, such as stability, solubility, and reactivity.
Used in Specialty Chemicals:
2-(2-CHLOROBENZYLOXY)BENZALDEHYDE is used as a precursor in the production of specialty chemicals. Its versatility in chemical reactions enables the creation of unique and highly specific chemical products for various industries.

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

Upstream product

• 90-02-8 salicylaldehyde 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 89-95-2 2-methyl-benzyl alcohol 
• 611-17-6 1-bromomethyl-2-chlorobenzene 

Downstream Products

• 1430841-84-1 2-(2-Chlorobenzyloxy)benzaldehyde O-quinuclidin-3-yl oxime 
• 496018-59-8 6-amino-4-[2-(2-chloro-benzyloxy)-phenyl]-3-trifluoromethyl-2,4-dihydro-pyrano[2,3-c]pyrazole-5-carbonitrile 
• 53390-12-8 2-(2'-chlorophenyl)benzo[b]furan 

Relevant articles and documents

Identification, Synthesis, and Biological Evaluations of Potent Inhibitors Targeting Type i Protein Arginine Methyltransferases

CARM1 (coactivator-associated arginine methyltransferase 1), which belongs to type I PRMTs (protein arginine methyltransferases), is a potential therapeutic target for treatment of multiple cancers. In this study, we first identified several hit compounds against CARM1 by structure-based virtual screening (IC50 = 35.51 ± 6.68 to 68.70 ± 8.12 μM) and then carried out chemical structural optimizations, leading to six compounds with significantly improved activities targeting CARM1 (IC50 = 18 ± 2 to 107 ± 6 nM). As a compound with an ethylenediamino motif, the most potent inhibitor, ZL-28-6, also exhibited potent inhibition against other type I PRMTs. Compared to the type I PRMT inhibitor from our previous work (DCPR049_12), ZL-28-6 showed increased potency against CARM1 and decreased activity against other type I PRMTs. Moreover, ZL-28-6 showed better antiproliferation activities toward a series of solid tumor cells than DCPR049_12, indicating its broad spectrum of anticancer activity. In addition, cellular thermal shift and Western blot assays validated that ZL-28-6 could target CARM1 in cells. Taken together, the inhibitor we identified could serve as a potent probe for studying CARM1's biological functions and shed light on the future design of novel CARM1 inhibitors with stronger activities and selectivities.

PRMTI Type methyltransferase inhibition active compound as well as preparation and application thereof

The invention relates to a compound with PRMT I-type methyltransferase inhibition activity and preparation and application thereof, wherein the compound has the structure shown I. The compound of the formula I has a good inhibition effect on PRMT I-type m

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

Potassium tert-Butoxide-Mediated Condensation Cascade Reaction: Transition Metal-Free Synthesis of Multisubstituted Aryl Indoles and Benzofurans

An efficient and facile method to synthesize valuable disubstituted 2-aryl indoles and benzofurans in good yields has been demonstrated, based on a tert-butoxide-mediated condensation reaction involving a vinyl sulfoxide intermediate. Products are obtained from N- or O-benzyl benzaldehydes using dimethyl sulfoxide as a carbon source. The methodology features a wide functional group tolerance and transition metal-free environment. Preliminary mechanistic studies suggest that the reaction involves a tandem aldol reaction/Michael addition/dehydrosulfenylation/isomerization sequence through an ionic protocol.

Hydride transfer reactions of 5-(2-alkohybenzylidene) barbituric acids: Synthesis of 2,4,6-trioxoperhydropyrimidine-5-spiro-3′-chromanes

The thermal cyclization of 5-(2-phenoxymethylphenyl-methylene)barbituric acid and its derivatives affords 2,4,6-trioxoperhydropyrimidine-5-spiro-3′-chromanes. The reactions require no catalysts and proceed at temperatures from 118 to 240?°C depending on the substrate activity. These cyclization reactions are analogous to T-reactions of tertiary amines involving the hydride transfer.

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.