794-94-5

Usage

Uses

4-Methoxybenzoic anhydride is used as pharmaceutical intermediates.

Synthesis Reference(s)

Synthetic Communications, 19, p. 3331, 1989 DOI: 10.1080/00397918908052736

InChI:InChI=1/C16H14O5/c1-19-13-7-3-11(4-8-13)15(17)21-16(18)12-5-9-14(20-2)10-6-12/h3-10H,1-2H3

Upstream product

• 100-07-2 4-methoxy-benzoyl chloride 
• 79-37-8 oxalyl dichloride 
• 100-09-4 4-methoxybenzoic acid 
• 3770-50-1 2-carbethoxyindole 
• 141-53-7 sodium formate 
• 103360-21-0 1-cyano-2-ethoxycarbonyl-1,2-dihydroisoquinoline 
• 201230-82-2 carbon monoxide 
• 100-66-3 methoxybenzene 
• 696-62-8 para-iodoanisole 
• 121-44-8 triethylamine 
• 123-11-5 4-methoxy-benzaldehyde 
• 98-95-3 nitrobenzene 
• 579-75-9 2-Methoxybenzoic acid 
• 105-13-5 4-Methoxybenzyl alcohol 

Downstream Products

• 108902-39-2 2-(4-methoxy-phenyl)-oxazolo[4,5-c]pyridine 
• 34170-18-8 3,5,6,7,8,4′-hexamethoxyflavone 
• 20869-95-8 ermanin 
• 6665-76-5 5-acetoxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 88856-50-2 5-hydroxy-4'-methoxy-3-(4''-methoxybenzoyl)flavone 
• 85734-53-8 7-hydroxy-3,4',5,8-tetramethoxyflavone 
• 14756-22-0 UCCF 269 
• 101597-74-4 1-(2-hydroxy-6-methoxyphenyl)-3-(4-methoxyphenyl)propane-1,3-dione 
• 125240-02-0 UCCF 040 
• 743438-43-9 8-hydroxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 480-44-4 5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one 
• 874519-13-8 5,7-dihydroxy-3-(4-methoxy-benzoyl)-2-(4-methoxy-phenyl)-chromen-4-one 
• 14004-55-8 5,7-Dihydroxy-2-(4-methoxyphenyl)-6-methyl-4H-1-benzopyran-4-one 
• 14004-54-7 8-methylacacetin 

Relevant academic research and scientific papers

Efficient synthesis of symmetrical anhydrides by cross dehydrogenative coupling of aryl aldehydes over CuFe2O4 nanoparticles

Nano copper ferrite catalyst is prepared and characterized by scanning electron microscopy, energy dispersive X-ray, X-ray diffraction, vibrational sample magnetometry, and Fourier transform infrared. The catalytic activity is probed for cross-dehydrogenative coupling of aromatic aldehydes in the presence of tert-butyl hydroperoxide as the oxidant. This catalytic protocol appears as a simple, rather cheap, clean, and efficient practical strategy for the synthesis of symmetrical anhydrides, with proper efficiency (66%). The catalyst can be easily separated from the reaction mixture by an external magnet and reused several times in subsequent reactions, without any measurable loss of its efficiency. Graphic abstract: [Figure not available: see fulltext.]

PPh3/Selectfluor-Mediated Transformation of Carboxylic Acids into Acid Anhydrides and Acyl Fluorides and Its Application in Amide and Ester Synthesis

By taking the advantage of PPh3/Selectfluor system, carboxylic acids are efficiently converted into the pivotal intermediates acyloxyphosphonium ions that can selectively react with a second carboxylic acid or fluoride to in situ yield the corresponding acid anhydrides or acyl fluorides. The developed protocol features commercially availabile reagents, no involvement of base, room temperature conditions, and simple experimental procedure. Additionally, various amides or esters are readily achieved, respectively, with the addition of amines or alcohols.

Vilsmeier-Haack reagent mediated synthetic transformations with an immobilized iridium complex photoredox catalyst

An immobilized iridium complex photocatalyst Ir(ppy)2(PDVB-py) was synthesized by immobilization of the iridium complex onto the nanoporous vinylpyridine-divinylbenzene copolymer (PDVB-py). Its application for the synthesis of amides, nitriles, and anhydrides was reported via reactions under the action of the visible-light-driven in situ generated Vilsmeier-Haack reagent from CBr4 in DMF. The results showed that this heterogeneous photocatalyst has extremely high activity and excellent stability to be recycled five times.

Organocatalytic Desymmetrisation of Fittig's Lactones: Deuterium as a Reporter Tag for Hidden Racemisation

Highly enantioselective desymmetrisation of Fittig's lactones with alcohols is promoted by bifunctional cinchona squaramides. The reactions were carried out with monodeuterated methanol to detect possible hidden racemisation of the stereogenic centre. Current evidence suggests that racemisation was not a relevant process for most substrates; partial erosion of enantioselectivity was only detected with ortho -substituted aryl derivates. The resultant glutaric acid derivatives possess a scaffold that is common in natural products and the compounds are also useful chiral building blocks for further synthetic endeavours.

PIII-Chelation-Assisted Indole C7-Arylation, Olefination, Methylation, and Acylation with Carboxylic Acids/Anhydrides by Rhodium Catalysis

Rhodium-catalyzed C7-selective decarbonylative arylation, olefination, and methylation of indoles with carboxylic acids or anhydrides by C?H and C?C bond activation have been developed. Furthermore, C7-acylation products can also be generated selectively at a lower reaction temperature in the developed system. The key to the high reactivity and regioselectivity of this transformation is the appropriate choice of an indole N-PtBu2 chelation-assisted group. This method has many advantages, including easy access and removal of the directing group, the use of cheap and widely available coupling agents, no requirement of an external ligand or oxidant, a broad substrate scope, high efficiency, and the formation of a sole regioisomer.

One-pot synthesis of thioesters with sodium thiosulfate as a sulfur surrogate under transition metal-free conditions

In this paper, we report an efficient synthetic method for thioester formation from sodium thiosulfate pentahydrate, organic halides, and aryl anhydrides. In the one-pot two-step reactions developed in this study, sodium thiosulfate was used as the sulfur surrogate for acylation with anhydrides, followed by substitution with organic halides through the in situ generation of thioaroylate. Furthermore, two important organic compounds could be successfully synthesized using our developed method. The advantages of the one-pot two-step reactions are operational simplicity, structurally diverse products with 42%-90% yields, use of relatively low toxic and odourless reagents, and easy applicability to large-scale operation.

Photocatalyic Appel reaction enabled by copper-based complexes in continuous flow

A copper-based photocatalyst, Cu(tmp)(BINAP)BF4, was found to be active in a photoredox Appel-type conversion of alcohols to bromides. The catalyst was identified from a screening of 50 complexes and promoted the transformation of primary and secondary alcohols to their corresponding bromides and carboxylic acids to their anhydrides. The protocol was also amendable and optimized under continuous flow conditions.

Synthesis, molecular docking, and pharmacological evaluation of N-(2-(3,5-dimethoxyphenyl)benzoxazole-5-yl)benzamide derivatives as selective COX-2 inhibitors and anti-inflammatory agents

A series of N-(2-(3,5-dimethoxyphenyl)benzoxazole-5-yl)benzamide derivatives (3am) was synthesized and evaluated for their in vitro inhibitory activity against COX-1 and COX-2. The compounds with considerable in vitro activity (IC50 50 values in the range of 0.06–0.71 μM. The in vivo anti-inflammatory activity of these six compounds (3a, 3b, 3d, 3g, 3j, and 3k) was assessed by the carrageenan-induced rat paw edema method. Compounds 3d (84.09%), 3g (79.54%), and 3a (70.45%) demonstrated significant anti-inflammatory activity compared to the standard drug ibuprofen (65.90%) and were also found to be safer than ibuprofen, by ulcerogenic studies. A docking study was done using the crystal structure of human COX-2, to understand the binding mechanism of these inhibitors to the active site of COX-2.

Synthesis, biological evaluation and docking study of a new series of di-substituted benzoxazole derivatives as selective COX-2 inhibitors and anti-inflammatory agents

A new series of substituted-N-(3,4-dimethoxyphenyl)-benzoxazole derivatives 13a–13p was synthesized and evaluated in vitro for their COX (I and II) inhibitory activity, in vivo anti-inflammatory and ulcerogenic potential. Compounds 13d, 13h, 13k, 13l and 13n exhibited significant COX-2 inhibitory activity and selectivity towards COX-2 over COX-1. These selected compounds were screened for their in vivo anti-inflammatory activity by carrageenan induced rat paw edema method. Among these compounds, 13d was the most promising analogs of the series with percent inhibition of 84.09 and IC50 value of 0.04 μM and 1.02 μM (COX-2 and COX-1) respectively. Furthermore, ulcerogenic study was performed and tested compounds (13d, 13h, 13k, 13l) demonstrated a significant gastric tolerance than ibuprofen. Molecular docking study was also performed with resolved crystal structure of COX-2 to understand the binding mechanisms of newly synthesized inhibitors in the active site of COX-2 enzyme and the results were found to be concordant with the biological evaluation studies of the compounds. These newly synthesized inhibitors also showed acceptable pharmacokinetic profile in the in silico ADME/T analyses.

Synthesis, biological evaluation and docking study of N-(2-(3,4,5-trimethoxybenzyl)benzoxazole-5-yl) benzamide derivatives as selective COX-2 inhibitor and anti-inflammatory agents

A series of N-(2-(3,4,5-trimethoxybenzyl)-benzoxazole-5-yl)benzamide derivatives (3a–3n) was synthesized and evaluated for its in vitro inhibitory activity against COX-1 and COX-2. The compounds with considerable in vitro activity (IC50 50 in the range of 0.14–0.69 μM. In vivo anti-inflammatory activity of these six compounds (3b, 3d, 3e, 3h, 3l and 3m) was assessed by carrageenan induced rat paw edema method. The compound 3b (79.54%), 3l (75.00%), 3m (72.72%) and 3d (68.18%) exhibited significant anti-inflammatory activity than standard drug ibuprofen (65.90%). Ulcerogenic activity with histopathological studies was performed, and the screened compounds demonstrated significant gastric tolerance than ibuprofen. Molecular Docking study was also performed with resolved crystal structure of COX-2 to understand the interacting mechanisms of newly synthesized inhibitors with the active site of COX-2 enzyme and the results were found to be in line with the biological evaluation studies of the compounds.