23731-06-8

Usage

Uses

Used in Pharmaceutical Industry:
5-(Chloromethyl)-2-hydroxybenzaldehyde is used as a synthetic intermediate for the creation of bis-heterocyclic derivatives and benzo-fused macrocycles. These complex molecules often possess valuable biological activities and can be utilized in the development of new drugs and therapeutic agents.
Used in Chemical Research:
In the field of chemical research, 5-(Chloromethyl)-2-hydroxybenzaldehyde serves as a versatile building block for the synthesis of novel compounds with potential applications in various industries. Its unique structure allows for the exploration of new chemical reactions and the development of innovative synthetic pathways.
Used in Material Science:
The compound can also be employed in material science for the development of new materials with specific properties. The synthesis of benzo-fused macrocycles containing oxazolone or imidazolone subunits can lead to the creation of advanced materials with applications in areas such as electronics, sensors, and energy storage.

InChI:InChI=1/C8H7ClO2/c9-4-6-1-2-8(11)7(3-6)5-10/h1-3,5,11H,4H2

Upstream product

• 50-00-0 formaldehyd 
• 90-02-8 salicylaldehyde 
• 15454-33-8 chloromethanol 
• 110-88-3 1,3,5-Trioxan 
• 90-01-7 salicylic alcohol 
• 108-95-2 phenol 
• 89-95-2 2-methyl-benzyl alcohol 

Downstream Products

• 188999-62-4 5-(tripropylammoniomethyl)salicylaldehyde chloride 
• 188999-63-5 5-(tributylammoniomethyl)salicylaldehyde chloride 
• 188999-61-3 N,N-diethyl-N-(3-formyl-4-hydroxybenzyl)ethanaminium chloride 
• 700375-42-4 N-(3-formyl-4-hydroxybenzyl)benzo-10-aza-15-crown-5 
• 1162119-15-4 5-diethylaminomethylsalicylaldehyde hydrochloride 
• 300708-20-7 N,N’-bis(5-chloromethylsalicylidene)ethylenediamine 
• 1073183-65-9 1-(3-formyl-4-hydroxybenzyl)-3-methylimidazolium hexafluorophosphate 
• 1073183-67-1 CH₃N₂C₃H₃CH₂C₆H₃(OH)CHNOH⁽¹⁺⁾*PF₆^(1-)=(CH₃NC₃H₃NCH₂C₆H₃(OH)CHNOH)PF₆ 
• 1580445-85-7 1-ethyl-3-(3-formyl-4-hydroxybenzyl)-1H-imidazol-3-ium chloride 
• 1580445-91-5 1-butyl-3-(3-formyl-4-hydroxybenzyl)-1H-imidazol-3-ium chloride 

Relevant academic research and scientific papers

Synthesis of novel bis(chromenes) and bis(chromeno[3,4-C]pyridine) incorporating piperazine moiety

Novel bis(2-oxo-2H-chromene) as well as bis(2-imino-2H-chromene) derivatives incorporating piperazine moiety were prepared by the cyclocondensation reaction of bis(2-hydroxybenzaldehyde) with two equivalents of each of the appropriate β-ketoesters or acetonitrile derivatives. The bis(2-imino-2H-chromene-3-carbothioamide) derivative was used as a key synthon for construction of novel bis(3-(4-substituted thiazol-2-yl)-2H-chromen-2-one) derivatives via its cyclocondensation with a series of the appropriate α-halocarbonyl derivatives. Moreover, the bis(2-hydroxybenzaldehyde) reacted with four equivalents of the appropriate acetonitrile derivatives to afford the corresponding bis(3H-chromeno[3,4-c]pyridine) derivatives. Elucidation of the structure of the novel bis(chromenes) bearing piperazine nucleus was established by the spectral data and elemental analyses.

Efficient synthesis and evaluation of bis-pyridinium/bis-quinolinium metallosalophens as antibiotic and antitumor candidates

Inspired with the pharmacological diversity of salophens and in our endeavor to explore a new strategy which may conflict the invasion of drug resistance, we report herein efficient synthetic routes for the synthesis of new RO-salophen(Cl), pyridinium/quinolinium-based salophens (3a-e) and metallosalophens (4a-j). These new architectures have been structurally characterized by elemental and spectral analysis as well pharmacologically evaluated for their in?vitro antimicrobial, against a common panel of pathogenic bacterial and fungal strains, and anticancer activities against human colon carcinoma (HCT-116) cell lines. Antimicrobial assay results revealed that all tested compounds exhibited moderate to superb broad-spectrum efficacy in comparison to the standard antibiotic with a preferential ability to perform as a fungicides than to act as bactericides. Noteworthy, VO(II)-salophens are more effective in reduction HCT-116?cell viability than Cu(II)-salophens. For example, VO(II)-salophen3 (4f) (IC50?=?2.13?μg/mL) was ca. 10-fold more efficient than Cu(II)-salophen3 (4e) (IC50?=?20.30?μg/mL).

Computational study on non-linear optical property of Wittig based Schiff-Base ligands (both Z & E isomers) & Copper(II) complex

96 new Wittig based Schiff-Base (WSB) ligands (both E & Z conformation) containing fused aromatic rings were designed and screened for NLO property. Wittig based precursor aldehydes were synthesized and spectroscopically confirmed. WSB ligands and their copper(II) complexes were also designed, optimized and their NLO property was studied using a GAUSSIAN09 computer program. For Optimization & Hyperpolarizability (β) calculations, DFT based B3LYP method was applied with LANL2DZ basis set for metal ion and 6-31G* basis set for C, H, N & O atoms. The study presents the Structure-Activity relationship (SAR) between WSB ligands and β. The study revealed that WSB Ligands of the category N2, which are those derived from precursor aldehyde, (2-hydroxy-5-(2-(naphthalen-1-yl)vinyl)benzaldehyde) encoded as PA-2, showed higher β values over N1, which are derived from, 2-hydroxy-5-(2-(naphthalen-1-yl)vinyl)benzaldehyde, encoded as PA-1. Among all ligands, Ligand-14, (E?4-(2-Pyren-1-yl-vinyl)-2-([1,2,4]triazol-4-yliminomethyl)-phenol), of N2 category showed highest β value (6.968 × 10?30 e.s.u). After complexing with Cu(II), encoded as Complex-1 ([(4-(2-Pyren-1-yl-vinyl)-2-([1,2,4]triazol-4-yliminomethyl)-phenoxy)2Cu], which has C2 symmetry, the β value (0.310 × 10?30 e.s.u) unexpectedly decreased. However, it is still high as compared to that of urea (β = 0.091 × 10?30 e.s.u). The output of TD-DFT also supports the obtained results. Different factors affecting β value especially their geometrical isomeric effect were successfully analyzed.

A selective and sensitive near-infrared fluorescent probe for real-time detection of Cu(i)

The disruption of copper homeostasis (Cu+/Cu2+) may cause neurodegenerative disorders. Thus, the need for understanding the role of Cu+ in physiological and pathological processes prompted the development of improved methods of Cu+ analysis. Herein, a new near-infrared (NIR) fluorescent turn-on probe (NPCu) for the detection of Cu+ was developed based on a Cu+-mediated benzylic ether bond cleavage mechanism. The probe showed high selectivity and sensitivity toward Cu+, and was successfully applied for bioimaging of Cu+ in living cells. This journal is

A novel ditopic zinc-salophen macrocycle: A potential two-stationed wheel for [2]-pseudorotaxanes

Crown ether macrocycle 1 including a zinc-salophen unit is obtained via a de novo synthetic design to give a potential pH-driven two-stationed wheel component of [2]-pseudorotaxane systems. The Royal Society of Chemistry.

Light-Induced Activation of a Molybdenum Oxotransferase Model within a Ru(II)-Mo(VI) Dyad

Nature uses molybdenum-containing enzymes to catalyze oxygen atom transfer (OAT) from water to organic substrates. In these enzymes, the two electrons that are released during the reaction are rapidly removed, one at a time, by spatially separated electron transfer units. Inspired by this design, a Ru(II)-Mo(VI) dyad was synthesized and characterized, with the aim of accelerating the rate-determining step in the cis-dioxo molybdenum-catalyzed OAT cycle, the transfer of an oxo ligand to triphenyl phosphine, via a photo-oxidation process. The dyad consists of a photoactive bis(bipyridyl)-phenanthroline ruthenium moiety that is covalently linked to a bioinspired cis-dioxo molybdenum thiosemicarbazone complex. The quantum yield and luminescence lifetimes of the dyad [Ru(bpy)2(L2)MoO2(solv)]2+ were determined. The major component of the luminescence decay in MeCN solution (?., = 1149 ± 2 ns, 67%) corresponds closely to the lifetime of excited [Ru(bpy)2(phen-NH2)]2+, while the minor component (?., = 320 ± 1 ns, 31%) matches that of [Ru(bpy)2(H2-L2)]2+. In addition, the (spectro)electrochemical properties of the system were investigated. Catalytic tests showed that the dyad-catalyzed OAT from dimethyl sulfoxide to triphenyl phosphine proceeds significantly faster upon irradiation with visible light than in the dark. Methylviologen acts as a mediator in the photoredox cycle, but it is regenerated and hence only required in stoichiometric amounts with respect to the catalyst rather than sacrificial amounts. It is proposed that oxidative quenching of the photoexcited Ru unit, followed by intramolecular electron transfer, leads to the production of a reactive one-electron oxidized catalyst, which is not accessible by electrochemical methods. A significant, but less pronounced, rate enhancement was observed when an analogous bimolecular system was tested, indicating that intramolecular electron transfer between the photosensitizer and the catalytic center is more efficient than intermolecular electron transfer between the separate components.

Experimental evaluation of cationic-Schiff base surfactants based on 5-chloromethyl salicylaldehyde for improving crude oil recovery and bactericide

In this study, a new family of cationic and cationic–Schiff Base surfactant was synthesized namely; N-(3-formyl-4-hydroxybenzyl)-N, N-dimethylhexadecan-1-aminium chloride (FHDHAC), (E)-N-(3-((butylimino)methyl)-4-hydroxybenzyl)-N,N-dimethylhexadecan-1-aminium chloride (4-IMHDAC), (E)-N-(3-((hexylimino)methyl)-4-hydroxybenzyl)-N,N-dimethylhexadecan-1-aminium chloride (6-IMHDAC) and (E)-N-(4-hydroxy-3-((octylimino) methyl)benzyl)-N,N-dimethylhexadecan-1-aminium chloride (8-IMHDAC) were prepared from 5-chloromethyl salicylaldehyde compound (5-CMS). The chemical structures of 5-CMS, 4-IMHDAC, 6-IMHDAC, and 8-IMHDAC are characterized using FTIR, 1H NMR instruments. The surface activity measurements of the prepared compounds showed a gradual increase in surface activity by increasing the alkyl chain length. Adsorption and micellization thermodynamic functions revealed the higher tendencies of the different surfactants towards adsorption at the organic/polar phase. The synthesized surfactants were evaluated in the enhanced oil recovery process and showed excellent efficiency (63.98%, 71.25%, and 75.72% for 4-IMHDAC, 6-IMHDAC, and 8-IMHDAC, respectively) during the recovery process near their critical micelle concentrations. The prepared surfactants showed high antimicrobial efficacy against different bacteria and fungi.

Synthesis and Antimicrobial Activity of (3-Formyl-4-hydroxybenzyl)triphenylphosphonium Chloride Acylhydrazones

Abstract: In this study, four novel quaternary phosphonium acylhydrazones, derivatives of (3-formyl-4-hydroxybenzyl)triphenylphosphonium chloride, have been synthesized and their structures elucidated from IR and NMR spectra, and elemental analysis. All synthesized compounds have been tested for their antimicrobial activity, and acylhydrazones have demonstrated selective activity against Gram-positive bacteria strains.

Topoisomerase i inhibition and DNA cleavage by zinc, copper, and nickel derivatives of 2-[2-bromoethyliminomethyl]-4-[ethoxymethyl]phenol complexes exhibiting anti-proliferation and anti-metastasis activity

Three transition metal derivatives (Zn, Cu, and Ni) of 2-[2-bromoethyliminomethyl]-4-[ethoxymethyl]phenol (L) were synthesized by the reaction of the metal salts with the Schiff base ligand in one pot. In the crystal structure of [Zn(L)Br], the Schiff base ligand binds to the metal center through its phenolate oxygen and imine nitrogen, and adopts a distorted tetrahedral geometry. These compounds were found to inhibit topoisomerase I (topo I) activity, induce DNA cleavage and show DNA binding activity. Moreover, these compounds were found to be cytotoxic towards several cancer cell lines (A2780, MCF-7, HT29, HepG2, A549, PC3, LNCaP) and prevent metastasis of PC3. Collectively, Cu(II) complex 2 shows superior activity relative to its Zn(II) and Ni(II) analogs.

Preparation of monodispersed metal-based infinite coordination polymer nanostructures and their good capability for metal oxide preparation

Two coordination polymer particles (Zn-CPP and Pb-CPP) were synthesized by reaction of metal(II) acetates with the sodium {3-[(4-carboxy-phenylimino)-methyl]-4-hydroxy-benzylsulfanyl}-acetate. The composition of CPPs was determined by elemental analyses which confirmed the presence of two metal ions per one organic linker in each monomeric unit. Photoluminescence studies of the prepared CPPs showed good correlation between the structure of CPPs and emission wavelengths. The calcination of Zn-CPP produced zinc oxide nanoparticles with large band gap and well defined morphology and composition.