28033-63-8

Usage

Uses

Used in Pharmaceutical Industry:
2-Methoxyphenylacetyl chloride is used as an acetylating agent for the synthesis of various pharmaceutical compounds. Its ability to attach an acetyl group to other molecules allows for the creation of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical industry, 2-Methoxyphenylacetyl chloride is utilized as a key intermediate in the production of various agrochemicals, contributing to the development of effective pesticides and other agricultural chemicals.
Used in Organic Compounds Synthesis:
2-Methoxyphenylacetyl chloride is used as a versatile intermediate in the synthesis of a wide range of organic compounds, including pharmaceuticals and fragrances. Its reactivity and ability to form acetyl derivatives make it a valuable component in the creation of diverse organic molecules with various applications.

InChI:InChI=1/C9H9ClO2/c1-12-8-5-3-2-4-7(8)6-9(10)11/h2-5H,6H2,1H3

Upstream product

• 79-37-8 oxalyl dichloride 
• 93-25-4 2-methoxyphenylacetic acid 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 7169-17-7 2-diazo-1-(2-methoxyphenyl)ethanone 
• 135-02-4 ortho-anisaldehyde 
• 90-02-8 salicylaldehyde 
• 121985-99-7 2-hydroxy-2-(2-methoxyphenyl)acetonitrile 

Downstream Products

• 124067-29-4 3-(2-anisyl)-α-diazo-2-propanone 
• 91497-59-5 1-acetoxy-3-(2-methoxy-phenyl)-acetone 
• 351155-93-6 (2-methoxy-phenyl)-acetic acid-(3,4-dimethoxy-phenethylamide) 
• 65200-70-6 2-(2-methoxyphenyl)-1-(4-methoxyphenyl)ethan-1-one 
• 101430-42-6 [(2-methoxy-phenyl)-acetyl]-malonic acid diethyl ester 
• 133534-81-3 2-(o-methoxyphenylacetyl)-1-cyclohexanone 
• 153687-07-1 3-[2-(2-Methoxy-phenyl)-acetylamino]-pyridine-2-carboxylic acid ethyl ester 
• 136559-44-9 2-(2-Methoxy-phenyl)-N,N-dipropyl-acetamide 
• 5211-62-1 1-(2-methoxyphenyl)propan-2-one 
• 349134-81-2 2-(2-methoxyphenyl)-1-(piperidin-1-yl)ethan-1-one 
• 864445-43-2 JWH 250 
• 75256-37-0 4-hydroxy-3-(o-methoxyphenyl)-1,2-dihydroquinolin-2-one 
• 75256-43-8 4-Chloro-3-(2-methoxy-phenyl)-1H-quinolin-2-one 
• 74384-37-5 1-(4-Hydroxy-3,5-dimethyl-phenyl)-2-(2-methoxy-phenyl)-ethanone 

Relevant academic research and scientific papers

Design, synthesis, biological evaluation and silico prediction of novel sinomenine derivatives

Sinomenine is a morphinan alkaloid with a variety of biological activities. Its derivatives have shown significant cytotoxic activity against different cancer cell lines in many studies. In this study, two series of sinomenine derivatives were designed and synthesized by modifying the active positions C1 and C4 on the A ring of sinomenine. Twenty‐three compounds were synthesized and characterized by spectroscopy (IR,1H‐NMR,13C‐NMR, and HRMS). They were further evaluated for their cytotoxic activity against five cancer cell lines, MCF‐7, Hela, HepG2, SW480 and A549, and a normal cell line, Hek293, using MTT and CCK8 methods. The chlorine‐containing compounds exhibited significant cytotoxic activity compared to the nucleus structure of sinomenine. Furthermore, we searched for cancer‐related core targets and verified their interaction with derivatives through molecular docking. The chlorine‐containing compounds 5g, 5i, 5j, 6a, 6d, 6e, and 6g exhibited the best against four core targets AKT1, EGFR, HARS and KARS. The molecular docking results were consistent with the cytotoxic results. Overall, results indicate that chlorine‐containing derivatives might be a promising lead for the development of new anticancer agents.

N-monoarylacetothioureas as potent urease inhibitors: synthesis, SAR, and biological evaluation

A urease inhibitor with good in vivo profile is considered as an alternative agent for treating infections caused by urease-producing bacteria such as Helicobacter pylori. Here, we report a series of N-monosubstituted thioureas, which act as effective urease inhibitors with very low cytotoxicity. One compound (b19) was evaluated in detail and shows promising features for further development as an agent to treat H. pylori caused diseases. Excellent values for the inhibition of b19 against both extracted urease and urease in intact cell were observed, which shows IC50 values of 0.16 ± 0.05 and 3.86 ± 0.10 μM, being 170- and 44-fold more potent than the clinically used drug AHA, respectively. Docking simulations suggested that the monosubstituted thiourea moiety penetrates urea binding site. In addition, b19 is a rapid and reversible urease inhibitor, and displays nM affinity to urease with very slow dissociation (koff=1.60 × 10?3 s?1) from the catalytic domain.

Resolution of Vaulted Biaryl Ligands via Borate Esters of Quinine and Quinidine

Given the sudden and unexplained rise in the cost of (+)- A nd (-)-sparteine, an alternative method for the resolution of vaulted biaryls has been developed. This method involves the reaction of a racemic vaulted biaryl ligand with one equivalent of BH3·SMe2 and one equivalent of either quinine or quinidine. A precipitate then forms from the resulting mixture of diastereomeric borates as a result of differential solubilities. Hydrolysis of the precipitate then liberates the (S)-ligand in the case of quinine and the (R)-ligand in the case of quinidine, both with >99% ee. This method has been applied to 16 different vaulted biaryl ligands, including 10 whose preparation is described here for the first time. In addition, proof of principle has been demonstrated for the dynamic thermodynamic resolution of the vaulted biaryl ligands with this method in combination with a nonchiral copper(II) complex that can racemize the ligand.

Palladium-Catalyzed Distal C?H Selenylation of 2-Aryl Acetamides with Diselenides and Selenyl Chlorides

A convenient and effective method of palladium-catalyzed C?H selenylation of the 2-aryl acetamides assisted with removable 8-aminoquinoline with readily available diselenides and selenyl chlorides has been developed. This selenylation reaction is scalable and tolerates a wide range of functional groups, providing a straightforward way of the preparing unsymmetrical diaryl selenides and dibenzoselene-pinone. Preliminary mechanistic studies indicated that a single-electron transfer type mechanism and facile C?H metalation are operative. (Figure presented.).

FUSED [1,2,4]THIADIAZINE DERIVATIVES WHICH ACT AS KAT INHIBITORS OF THE MYST FAMILY

A compound of formula (I): which inhibits the activity of one or more KATs of the MYST family, i.e., TIP60, KAT6B, MOZ, HBO1 and MOF.

Formamide catalyzed activation of carboxylic acids-versatile and cost-efficient amidation and esterification

A novel, broadly applicable method for amide C-N and ester C-O bond formation is presented based on formylpyrrolidine (FPyr) as a Lewis base catalyst. Herein, trichlorotriazine (TCT), which is the most cost-efficient reagent for OH-group activation, was employed in amounts of ≤40 mol% with respect to the starting material (100 mol%). The new approach is distinguished by excellent cost-efficiency, waste-balance (E-factor down to 3) and scalability (up to >80 g). Moreover, high levels of functional group compatibility, which includes acid-labile acetals and silyl ethers, are demonstrated and even peptide C-N bonds can be formed. In comparison to reported amidation procedures using TCT, yields are considerably improved (for instance from 26 to 91%) and esterification is facilitated for the first time in synthetically useful yields. These significant enhancements are rationalized by activation by means of acid chlorides instead of less electrophilic acid anhydride intermediates.

Preparation of Organic Nitrates from Aryldiazoacetates and Fe(NO3)3·9H2O

A thermal protocol is reported for the formal insertion of nitric acid into aryldiazoacetates using Fe(NO3)3·9H2O. This strategy is mild and high yielding and allows the preparation of a large variety of members of an unprecedented family of organic nitrates. The nitrate group can be also readily transformed into other functional groups and heterocyclic moieties and can possibly allow new biological explorations of untapped potential associated with their NO-releasing ability.

Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by In Situ Generation of a Directing Group

A general synthesis of highly substituted 2-naphthols based on a new carbanionic reaction sequence is demonstrated. The reaction exploits the dual nature of lithium bases consisting of consecutive ring opening of readily available coumarins with either LiNEt2 or LiNiPr2 into Z-cinnamamides, thus generating a directing group in situ and allowing, by conformational freedom, a lateral directed remote metalation for ring closure to give the aryl 2-naphthols in good to excellent yields. These transformations can be combined to provide a more efficient one-pot process. Mechanistic insight into the remote lateral metalation step, demonstrating the requirement of Z-cinnamamide, is described. Application of this methodology to the synthesis of highly substituted 3,3′-diaryl BINOL ligands is also reported.

Reducing the Flexibility of Type II Dehydroquinase for Inhibition: A Fragment-Based Approach and Molecular Dynamics Study

A multidisciplinary approach was used to identify and optimize a quinazolinedione-based ligand that would decrease the flexibility of the substrate-covering loop (catalytic loop) of the type II dehydroquinase from Helicobacter pylori. This enzyme, which i

Synthesis of Unsymmetrical Diaryl Acetamides, Benzofurans, Benzophenones, and Xanthenes by Transition-Metal-Free Oxidative Cross-Coupling of sp3 and sp2 C-H Bonds

A chemo- and regioselective intermolecular sp3 C-H and sp2 C-H coupling reaction for C-C bond formation is described to access unsymmetrical diaryl acetamides under TM-free conditions from sec- and tert-arylacetamides and nitroarenes using tert-butoxide base in DMSO at room temperature. The coupling partners with sensitive functionalities such as chloro, bromo, hydroxy, and cyano were also amenable to the developed reaction. Synthesized α-(2/4-nitroaryl) phenylacetamides have been transformed into biologically important benzofurans, xanthenes, diaryl indoles, and unsymmetrical benzophenones by novel routes without applying a transition metal. Overall, an economical, yet efficient, strategy has been devised to access unsymmetrical diarylacetamides with the possibility of their further elaboration into a variety of biologically important heterocycles. Mechanistic understanding suggests that the reaction proceeds by a nucleophilic addition of a phenylacetamide carbanion, which is generated in the presence of tert-butoxide base, to the para or ortho (if para is substituted) position of nitrobenzene. The formed α-(4-nitrocyclohexa-2,4-dien-1-yl) phenylacetamide anion intermediate oxidized by a basic solution of DMSO or atmospheric oxygen led to the desired sp3 C-H and sp2 C-H coupled α-(2/4-nitroaryl) phenylacetamides.