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
• Article Data: 7

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

General Description

2-(2-chlorobenzyloxy)benzaldehyde is a chemical compound with the molecular formula C14H11ClO2. It is an aldehyde with a benzene ring, chloro substituent, and an ether linkage. 2-(2-CHLOROBENZYLOXY)BENZALDEHYDE is often used as a building block in the synthesis of various organic compounds and pharmaceuticals. It is commonly utilized in the production of dyes, polymers, and other specialty chemicals. The chemical is known for its aromatic properties and is generally considered to be stable under normal conditions. It is important to handle this compound with care and follow proper safety protocols due to its potential health hazards.

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 
• 611-17-6 1-bromomethyl-2-chlorobenzene 
• 89-95-2 2-methyl-benzyl alcohol 
• 17849-38-6 2-Chlorobenzyl alcohol 

Downstream Products

• 53390-12-8 2-(2'-chlorophenyl)benzo[b]furan 
• 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 

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.

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.