52411-35-5

Basic information

• Product Name: 5-ETHYL-2-HYDROXY-BENZALDEHYDE
• Synonyms: 5-ETHYL-2-HYDROXY-BENZALDEHYDE;5-ETHYL-2-HYDROXYBENZENECARBALDEHYDE;4-Ethyl-2-formylphenol, 5-Ethylsalicylaldehyde
• CAS NO: 52411-35-5
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17
• Mol File: 52411-35-5.mol

Chemical Properties

• Boiling Point: 238.1 °C at 760 mmHg
• Flash Point: 97.2 °C
• Appearance: /
• Density: 1.134 g/cm³
• Vapor Pressure: 0.028mmHg at 25°C
• Refractive Index: 1.586
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-ETHYL-2-HYDROXY-BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-ETHYL-2-HYDROXY-BENZALDEHYDE(52411-35-5)
• EPA Substance Registry System: 5-ETHYL-2-HYDROXY-BENZALDEHYDE(52411-35-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36
• Safety Statements: 26
• HazardClass: IRRITANT
• Hazardous Substances Data: 52411-35-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H10O2/c1-2-7-3-4-9(11)8(5-7)6-10/h3-6,11H,2H2,1H3

Upstream product

• 50-00-0 formaldehyd 
• 123-07-9 4-Ethylphenol 
• 67-66-3 chloroform 

Downstream Products

• 29922-49-4 2-hydroxymethyl-4-ethylphenol 
• 120389-43-7 {N,N'-bis(5-ethylsalicylidene)ethylenediaminato}nickel(II) 
• 1173429-51-0 N-[6-ethyl-4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]-N-methylamine 
• 1238575-89-7 2-amino-6-ethyl-4-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-4H-chromene-3-carbonitrile 
• 1257423-39-4 C₂₄H₂₄N₂O₂ 
• 75668-94-9 2-cyano-4-ethylphenol 
• 908002-67-5 C₂₁H₂₄O₄ 
• 179728-39-3 (2-formyl-4-ethylphenoxy)acetaldehyde diethyl acetal 

Relevant articles and documents

In Vitro Antitumor Activity of Newly Synthesized Pyridazin-3(2H)-One Derivatives via Apoptosis Induction

Systemic toxicity associated with drug resistance continues to be the major obstacle to curative therapy of cancer. Tumor cell resistance to chemotherapeutic drugs often results in coordinate resistance to other structurally and functionally unrelated drugs and the subsequent development of cross resistance phenotype. Therefore, it seems necessary to identify new molecules as anticancer agents. In this process, we synthesized a series of new pyridazin-3(2H)-one derivatives and evaluated their antitumor potential. These cyclic molecules were synthesized and designed as a combination of benzofuran with pyridazinones. All final compounds have been characterized by spectral and elemental analyses to confirm successful synthesis reactions. To evaluate their anticancer activity, all derivatives were assessed against the human breast adenocarcinoma cell line (MCF-7) and the murine mastocytoma cell line (P815) using the methyl tetrazolium Test (MTT assay). The cytotoxic activity was found to be dose-dependent and the IC50 values of the synthesized compounds ranged from 14.5 to 40 μM against MCF-7 and from 35 to 82.5 μM against P815. At the same time, no cytotoxic activity was observed against normal cells. In order to investigate the molecular mechanism of the most cytotoxic product (6f), apoptosis induction was measured against MCF-7 cells. Using the annexin-V FITC staining technique, we showed that the cytotoxic effect of this product is associated with apoptosis induction.

Synthesis, anti-inflammatory evaluation in vivo and docking studies of some new 5-(benzo[b]furan-2-ylmethyl)-6-methyl-pyridazin-3(2H)-one derivatives

Seven novel 5-(benzo[b]furan-2-ylmethyl)-6-methyl-pyridazin-3(2H)-one derivatives (6a to 6g) have been synthesized by the condensation of appropriate 3-(benzofuran-2-ylmethylene)-4-oxopentanoic acid and hydrazine hydrate in ethanol. Structures of all compounds were elucidated by elemental analysis, IR, 1H NMR and 13C NMR. These compounds were tested for their anti-inflammatory activity in carrageenan-induced rat paw edema model. In silico molecular docking study has been executed to study the binding interactions of the synthesized compounds with COX-2 protein. Compounds 6a, 6b, 6e and 6g showed a good anti-inflammatory activity at 50 mg/kg compared with the indometacin at 10 mg/kg and the aspirin at 150 mg/kg and good binding affinity with COX-2.

Efficient microwave-assisted regioselective one pot direct: Ortho -formylation of phenol derivatives in the presence of nanocrystalline MgO as a solid base catalyst under solvent-free conditions

In this research, at first nanocrystalline MgO was prepared and then the solvent-free reactions of phenol derivatives with paraformaldehyde in the presence of the obtained nanocrystalline MgO as a new catalyst under microwave irradiation were investigated. In this reaction, ortho-hydroxyaromatic aldehydes were yielded as products. This method seems to be comparable with other reported methods due to its high yield and regioselectivity. The significant features of this method are short reaction times, high yields, and easy and quick isolation of the products.

One-Pot Synthesis of Functionalized Fused Furans via a BODIPY-Catalyzed Domino Photooxygenation

Six-membered ring fused furans containing a tetrasubstituted tertiary carbon were prepared in an unprecedented one-pot BODIPY-catalyzed domino photooxygenation/reduction process. A series of functionalized furans was synthesized from readily available 2-alkenylphenols and mechanistic studies were performed to account for the domino photosensitized oxygenation.

Efficient synthesis of chiral benzofuryl β-amino alcohols via a catalytic asymmetric Henry reaction

Chiral β-amino alcohol ligands were found effective for the copper(ii)-catalyzed asymmetric Henry reaction of benzofuran-2-carbaldehydes with nitromethane, which led to the formation of (S)-enriched benzofuryl β-nitro alcohols with satisfactory enantioselectivities (up to 98% ee). Using this catalytic protocol, bioactive (S)-benzofuryl β-amino alcohols could be conveniently prepared in short steps.

Synthesis and antidepressant activity of 5-(benzo[b]furan-2-ylmethyl)-6-methylpyridazin-3(2H)-one derivatives

A new series of pyridazin-3-one derivatives were designed, synthesized and evaluated for their preclinical antidepressant effect on Swiss mice. Among the series, compounds 6c, 6d and 6f exhibited significant activity profile in forced swimming test. Compounds 6c and 6d were most efficacious, which at dose of 50 mg kg-1 reduced the time of immobility by 42.85 and 38.09 %, respectively, as compared to the standard drug fluoxetine which reduced the immobility time by 45.23 % at the dose of 32 mg kg-1. All the test and standard compounds were administered orally 60 min before the test. Interestingly, all active compounds did not cause any significant alteration of locomotor activity in mice as compared to control, indicating that the hybrids did not produce any motor impairment effects. The results indicate that pyridazin-3(2H)-one derivatives may have potential therapeutic value for the management of mental depression.

COMPOUNDS USEFUL FOR THE TREATMENT OF METABOLIC DISORDERS AND SYNTHESIS OF THE SAME

The present invention provides compounds of Formula (I): wherein variables X, Y, Z and R1 are as described herein. Some of the compounds described herein are glutamate dehydrogenase activators. The invention is also directed to pharmaceutical compositions comprising these compounds, uses of these compounds and compositions in the treatment of metabolic disorders as well as synthesis of the compounds.

Facile one-pot transformation of phenols into o-cyanophenols

The treatment of phenols with paraformaldehyde in the presence of MgCl2 and Et3N in THF at 80 C, followed by reaction with molecular iodine and aq. ammonia at room temperature provided the corresponding o-cyanophenols in moderate to good yields. The present reaction is a one-pot transformation of phenols into o-cyanophenols using much less expensive reagents than are typically used; the reaction is free of both transition-metals and cyanide. The utility of this reaction was highlighted during our preparation of Febuxostat from p-bromophenol.

Potent nematicidal activity of phthalaldehyde, salicylaldehyde, and cinnamic aldehyde against Meloidogyne incognita

The nematicidal activity of selected aromatic aldehydes was tested against the root knot nematode Meloidogyne incognita. The most active aldehyde was phthalaldehyde (1) with an EC50 value of 11 ± 6 mg/L followed by salicylaldehyde (2) and cinnamic aldehyde (3) with EC50 values of 11 ± 1 and 12 ± 5 mg/L, respectively. On the other hand, structurally related aldehydes such as 2-methoxybenzaldehyde (21), 3,4-dimethoxybenzaldehyde, and vanillin (23) were not active at the concentration of 1000 mg/L. By liquid chromatography-mass spectrometry the reactivity of tested aldehydes against a synthetic peptide resembling the nematode cuticle was characterized. At the test concentration of 1 mM, the main adduct formation was observed for 3,4-dihydroxybenzaldehyde (22), 2-methoxybenzaldehyde (21), and 3,4-dimethoxybenzaldehyde. Considering that 2-methoxybenzaldehyde (21) and 3,4-dimethoxybenzaldehyde were not active against M. incognita in in vitro experiments led us to hypothesize a different mechanism of action rather than an effect on the external cuticle modification of nematodes. When the toxicity of the V-ATPase inhibitor pyocyanin (10) was tested against M. incognita J2 nematodes, an EC50 at 24 h of 72 ± 25 mg/L was found. The redox-active compounds such as phthalaldehyde (1) and salicylaldehyde (2) may share a common mode of action inhibiting nematode V-ATPase enzyme. The results of this investigation reveal that aromatic redox-active aldehydes can be considered as potent nematicides, and further investigation is needed to completely clarify their mode of action.

The synthesis of 2-hydroxymethyl derivatives of phenols

2-Hydroxymethylphenols have been prepared in good yield by reduction with sodium borohydride of the precursor aldehydes, obtained regiospecifically from reaction of phenols with paraformaldehyde in toluene containing stannic chloride and tri-n-butylamine. By contrast, reaction of phenols with either paraformaldehyde under anhydrous conditions or with aqueous formaldehyde results in formation of both the hydroxymethyl and the bishydroxymethyl derivatives. Cyclic acetals of the precursor aldehydes are readily accessible.