4251-63-2

Usage

Uses

Used in Pharmaceutical Industry:
(2-Chlorophenyl)acetaldehyde is used as a synthetic intermediate for the preparation of regioand stereoselective α-fluorinated amides. These amides are important in the development of new pharmaceuticals, particularly those targeting specific biological receptors or enzymes.
Used in Chemical Research:
In the field of chemical research, (2-Chlorophenyl)acetaldehyde serves as a key building block for the synthesis of regioselective 1,4-disubstituted 1,2,3-triazoles. These triazoles are valuable compounds with diverse applications, including their use as ligands, catalysts, and in the development of new materials with unique properties.
Overall, (2-Chlorophenyl)acetaldehyde is a versatile compound with significant potential in both the pharmaceutical industry and chemical research, contributing to the development of new drugs and advanced materials.

InChI:InChI=1/C8H7ClO/c9-8-4-2-1-3-7(8)5-6-10/h1-4,6H,5H2

Upstream product

• 135879-72-0 [(E)-2-(2-Chloro-phenyl)-vinyl]-carbamic acid methyl ester 
• 19819-95-5 2-(2-chlorophenyl)-1-ethanol 
• 2039-87-4 2-chlorostyrene 
• 2444-36-2 2'-chloro-benzeneacetic acid 
• 615-41-8 2-iodochlorobenzene 
• 15851-90-8 (E)-3-(2-chlorophenyl)acrylamide 

Downstream Products

• 4311-00-6 (2-chloro-phenyl)-acetaldehyde-semicarbazone 
• 46322-07-0 C₉H₁₁ClN₄ 
• 99846-64-7 2-(2-Chlorophenyl)-N-methylacetamide 
• 701-06-4 1-(2′-chlorophenyl)-2-propanol 
• 6282-87-7 3-(2-chlorophenyl)-propanol 
• 52516-17-3 2-(2-chlorochlorophenyl)-N-methylethanamine 
• 141438-36-0 N'-tert-Butyl-N-[2-(2-chloro-phenyl)-ethyl]-N-methyl-formamidine 
• 1065495-62-6 (Z)-N-(2-propynyl)-N'-[2-(2-chlorophenyl)ethylidene]hydrazine 
• 1065495-27-3 (E)-N-(2-propynyl)-N'-[2-(2-chlorophenyl)ethylidene]hydrazine 
• 1359070-93-1 1-(2-chlorobenzyl)-2-p-toluenesulfonyl-1,2,3,4-tetrahydroisoquinolin-7-ol 
• 1565471-28-4 N¹-(2-chlorophenethyl)-N³,N³-dimethylpropane-1,3-diamine 
• 13178-02-4 4-(2-chlorophenyl)-1-phenyl-1H-1,2,3-triazole 

Relevant academic research and scientific papers

Regioselective, Diastereoselective, and Enantioselective One-Pot Tandem Reaction Based on an in Situ Formed Reductant: Preparation of 2,3-Disubstituted 1,5-Benzodiazepine

The 1,5-benzodiazepines are important skeletons frequently contained in medicinal chemistry. Herein, we described an unexpected tandem cyclization/transfer hydrogenation reaction for obtaining chiral 2,3-disubstituted 1,5-benzodiazepines. The enolizable aryl aldehydes were chosen as substrates to react with symmetric and unsymmetric o-phenylenediamines. The unforeseen tandem reaction occurred among many possible latent side reactions under chiral phosphoric acid catalysis and affords the corresponding products in moderate yields and regioselectivities, good diastereoselectivities, and enantiomeric ratio (up to 99:1).

Peroxygenase-Catalysed Epoxidation of Styrene Derivatives in Neat Reaction Media

Biocatalytic oxyfunctionalisation reactions are traditionally conducted in aqueous media limiting their production yield. Here we report the application of a peroxygenase in neat reaction conditions reaching product concentrations of up to 360 mM.

Stereoselective synthesis of 3,4-di-substituted mercaptolactones via photoredox-catalyzed radical addition of thiophenols

A visible light mediated radical addition of thiophenols on 4-phenylbut-3-enoic acids to give diastereoselective synthesis of 3,4-disubstituted γ-lactones is reported. The reaction precludes the conventional prerequisite of conjugate addition. Furthermore, the lactones were successfully utilized in the synthesis of γ-ketoamides.

Synthesis of a novel six membered CNS palladacycle; TD-DFT study and catalytic activity towards microwave-assisted selective oxidation of terminal olefin to aldehyde

This article documented synthesis of a Schiff base, E-2-(benzylthio)-N-{(2-methoxynaphthalene-1-yl)methylene}benzenamine (HL) by the treatment of 2-meyhoxynaphthaldehyde and 2-(benzylthio)aniline. Reaction of this synthesized Schiff base with Na2PdCl4has been investigated, which gave a novel six membered Pd(II) complex (PdLCl) through C,N,S-donor atom of Schiff base. These two newly synthesized compounds were characterized by1H NMR, FTIR and UV–Vis spectra and structure of the Pd(II) complex was confirmed by X-ray crystallography. The catalyst (PdLCl) displayed considerable reactivity (up to 99% selectivity and 90% yield) in the selective oxidation of terminal [Formula presented] bond in aryl substituted olefin to aldehyde. The method shows good functional groups compatibility, no ketone byproducts and is operationally simple. Time dependent density functional study (TD-DFT) of representative cyclopalladated complex has been undertaken. The simulated optical spectrum of the complex is in good agreement with the experimentally observed spectrum.

Maleimide-assisted anti-Markovnikov Wacker-type oxidation of vinylarenes using molecular oxygen as a terminal oxidant

Arylacetaldehydes were successfully synthesized by the anti-Markovnikov Wacker-type oxidation of vinylarenes using 1 atm O2 as a terminal oxidant under mild conditions. Electron-deficient alkenes, such as maleic anhydride and maleimides, were effective additives and would operate as ligands to stabilize the Pd(0) species during the reaction.

Selective oxidation of terminal aryl and aliphatic alkenes to aldehydes catalyzed by iron(iii) porphyrins with triflate as a counter anion

[Fe(Por)CF3SO3] (Por = porphyrin dianion) can efficiently catalyze selective oxidation of terminal aryl alkenes and aliphatic alkenes to aldehydes in good to high yields under mild conditions.

HYDROXAMATE-BASED INHIBITORS OF DEACETYLASES B

The present teachings relate to compounds of Formula I: and pharmaceutically acceptable salts, hydrates, esters, and prodrugs thereof, wherein R1, R2, R3, Y, Z, and are as defined herein. The present teachings also provide methods of preparing compounds of Formula I and methods of using compounds of Formula I in treating, inhibiting, or preventing pathologic conditions or disorders mediated wholly or in part by deacetylases.

TRIAZINE COMPOUNDS AS KINASE INHIBITORS

The present invention relates to triazine compounds that are useful as kinase inhibitors. More particularly, the present invention relates to morpholino substituted triazines, methods for their preparation, pharmaceutical compositions containing these compounds and uses of these compounds in the treatment of proliferative disorders. These compounds may be useful as medicaments for the treatment of a number of proliferative disorders including tumours and cancers as well as other disorders or conditions related to or associated with mTOR kinases or PI3 kinases. The compounds are of the formula (I)

N-Propynyl analogs of β-phenylethylidenehydrazines: Synthesis and evaluation of effects on glycine, GABA, and monoamine oxidase

A group of β-phenylethylidenehydrazines possessing a variety of substituents (Me, OMe, Cl, F, and CF3) at the ortho-, meta-, or para-positions of the phenyl ring, in conjunction with either a N-bis-(2-propynyl) or a N-mono-(2-propynyl) moiety, were synthesized and compared to the novel neuroprotective drug β-phenylethylidenehydrazine (PEH) with regard to their ability to inhibit the enzymes GABA-transaminase (GABA-T) and monoamine oxidase (MAO)-A and -B in vitro in brain tissue. Two of the analogs synthesized (mono- and bis-N-propynylPEH) were also studied ex vivo in rats to compare their effects to those of PEH with regard to ability to inhibit GABA-T and MAO and to change brain levels of several important amino acids. Unlike PEH, none of the new drugs inhibited GABA-T in vitro at 10 or 100 μM, and all of the drugs (including PEH) were poor inhibitors (at 10 μM) of MAO-A and -B in vitro. The two analogs studied ex vivo inhibited GABA-T to a lesser extent than PEH, unlike PEH that did not elevate brain levels of GABA, and inhibited MAO-A and -B more potently than PEH. Interestingly, unlike PEH, the two analogs caused marked increases in brain levels of glycine; because of the current interest in drugs that increase glycine availability in the brain as potential antipsychotic drugs, these two analogs now warrant further investigation.

Design and biological evaluation of phenyl-substituted analogs of β-phenylethylidenehydrazine

β-Phenylethylidenehydrazine (PEH) has been demonstrated previously to be an inhibitor of γ-aminobutyric acid transaminase (GABA-T) and to cause a marked increase in rat brain levels of GABA, a major neurotransmitter. A group of PEH analogs, possessing a variety of substituents (Me, OMe, Cl, F, and CF3) at the 2-, 3-, and 4-positions of the phenyl ring, were synthesized for evaluation as inhibitors of GABA-T. The details of the synthesis and chemical characterization of the analogs are described. Preliminary in vitro screening for GABA-T inhibition showed that all the analogs possessed activity against this enzyme, although substitution of CF3 at the 2- and 4-positions caused reduced activity. One of the drugs, 4-fluoro-β- phenylethylidenehydrazine, was investigated further ex vivo, where it was shown to inhibit GABA-T, elevate brain levels of GABA, and decrease levels of glutamine, similar to the profile observed previously for PEH.