4442-54-0

Usage

Uses

Used in Pharmaceutical Industry:
1,4-Benzodioxane-6-carboxylic acid is used as a key intermediate in the synthesis of new anti-inflammatory compounds containing the 1,4-benzodioxine system. These compounds have the potential to provide relief from inflammation and pain, making them valuable in the development of medications for various inflammatory conditions.
Used in Chemical Synthesis:
1,4-Benzodioxane-6-carboxylic acid can also be utilized as a building block in the preparation of other organic compounds, particularly those with the 1,4-benzodioxine system. This system is found in various biologically active molecules, making the carboxylic acid a versatile starting material for the synthesis of a wide range of chemical products.

InChI:InChI=1/C9H8O4/c10-9(11)6-1-2-7-8(5-6)13-4-3-12-7/h1-2,5H,3-4H2,(H,10,11)/p-1

Upstream product

• 2879-20-1 1,4-benzodioxan-6-yl methyl ketone 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 106-93-4 ethylene dibromide 
• 29668-44-8 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde 
• 493-09-4 benzo-1,4-dioxane 
• 57744-67-9 6-iodo-1,4-benzodioxane 
• 109-77-3 malononitrile 
• 20197-75-5 2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester 
• 124-38-9 carbon dioxide 
• 39270-39-8 (2,3-dihydro-benzo[1,4]dioxin-6-yl)-methanol 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 67200-27-5 6-vinyl-2,3-dihydrobenzo[b][1,4]dioxine 
• 1370460-20-0 C₁₉H₁₉NO₃ 
• 590-29-4 potassium formate 

Downstream Products

• 57672-33-0 4,5-(ethylenedioxy)-2-nitrobenzoic acid 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 99358-09-5 7-amino-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylic acid 
• 51-61-6 dopamine 
• 129791-55-5 4-[(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-amino]-benzoic acid 
• 129791-54-4 ethyl 4-(2,3-dihydrobenzo[b][1,4]dioxin-6-carboxamido)benzoate 
• 98953-13-0 2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylic acid hydrazide 
• 1011726-49-0 C₃₅H₃₄N₂O₆S 
• 1011726-50-3 C₃₆H₃₆N₂O₆S 
• 1011726-51-4 C₃₆H₃₃F₃N₂O₆S 
• 1011726-52-5 C₃₆H₃₆N₂O₆S 
• 198554-08-4 4-[1-(2,3-dihydro-1,4-benzodioxin-6-ylcarbonyl)piperidin-4-yl]-6-(4-methoxybenzyl)pyrimidin-2-amine 
• 891260-82-5 C₂₆H₂₉N₃O₄ 
• 1186388-61-3 C₂₀H₁₉N₃O₃S 

Relevant academic research and scientific papers

1,2-Dibutoxyethane-Promoted Oxidative Cleavage of Olefins into Carboxylic Acids Using O2 under Clean Conditions

Herein, we report the first example of an effective and green approach for the oxidative cleavage of olefins to carboxylic acids using a 1,2-dibutoxyethane/O2 system under clean conditions. This novel oxidation system also has excellent functional-group tolerance and is applicable for large-scale synthesis. The target products were prepared in good to excellent yields by a one-pot sequential transformation without an external initiator, catalyst, and additive.

Potent arylamide derivatives as dual-target antifungal agents: Design, synthesis, biological evaluation, and molecular docking studies

Fungal infections have become a serious medical problem due to the high infection rate and the frequent emergence of drug resistance. Ergosterol is an important structural component of the fungal cell membrane, its synthetases (squalene epoxidase (SE) and 14α-demethylase (CYP51)) are considered as the key points to block the ergosterol synthesis. In this study, we designed a series of dual-target arylamides derivatives based on the analysis of active sites (SE, CYP51). Subsequently, these target compounds were synthesized, and their antifungal activity was evaluated. Most of compounds demonstrate the potent antifungal activity against multiple Candida spp. and A. fum. In particular, the antifungal activities of compounds 10b and 11c are not only superior to positive control drugs, but also have significant inhibitory effects on drug-resistant fungi (C.alb. Strain100, C.alb. Strain103). Therefore, their action mechanism was further studied. Cellular uptake and electron microscopy observation showed that target compounds were able to enter fungal cytoplasmic region through free diffusion, and destroyed cell membrane structure. At the same time, preliminary mechanisms have demonstrated that they can affect the synthesis of ergosterol by inhibiting the activity of dual targets. It is worth noting that they also can exhibit excellent antifungal activity and low toxic side effects in vivo. Their ADMET properties and binding models were established will be useful for further lead optimization.

Bis(methoxypropyl) ether-promoted oxidation of aromatic alcohols into aromatic carboxylic acids and aromatic ketones with O2 under metal- and base-free conditions

We describe an eco-friendly, practical and operationally simple procedure for the bis(methoxypropyl) ether-promoted oxidation of aromatic alcohols into aromatic carboxylic acids and aromatic ketones with atmospheric dioxygen as the sole oxidant. This chemical process is clean with high conversion and good selectivity, and an external initiator, catalyst, additive and base are not required. The virtue of this reaction is highlighted by its easily available and economical raw materials and excellent functional group tolerance (acid-, base- and oxidant-labile groups).

Preparation method of 2,3-dihydro-1,4-benzodioxane-6-carboxylic acid compound

The invention relates to a preparation method of a 2,3-dihydro-1,4-benzodioxane-6-carboxylic acid compound. The method comprises the following steps: carrying out a ring closing reaction on a raw material 3,4-dihydroxy benzaldehyde and 1,2-dibromoethane under alkaline conditions to obtain an intermediate 2,3-dihydro-1,4-benzodioxane-6-carboxaldehyde, purifying the intermediate, and carrying out an oxidation reaction on the purified intermediate in an aqueous potassium permanganate solution to obtain the 2,3-dihydro-1,4-benzodioxane-6-carboxylic acid compound. The method has the advantages of cheap and easily available raw materials, mild reaction conditions, simple post-treatment process, simple operation, high chemical yield, good application prospect, and suitableness for industrial production.

Direct carboxylation of simple arenes with CO2 through a rhodium-catalyzed C-H bond activation

Direct carboxylation of simple arenes under atmospheric pressure of CO2 is achieved through a rhodium-catalyzed C-H bond activation without the assistance of a directing group. Various arenes such as benzene, toluene, xylene, electron-rich or electron-deficient benzene derivatives, and heteroaromatics are directly carboxylated with high TONs. This journal is

Synthesis, structure, and urease inhibitory activities of three binuclear copper(II) complexes with protocatechuic acid derivative

Three Cu(II) complexes, [CuII2(L1) 4(L2)2] (1), [CuII 2(L1)4(H2O)2]·HL (2), and [CuII2(L1)

Effective palladium-catalyzed hydroxycarbonylation of aryl halides with substoichiometric carbon monoxide

A protocol for the Pd-catalyzed hydroxycarbonylation of aryl iodides, bromides, and chlorides has been developed using only 1-5 mol % of CO, corresponding to a pCO as low as 0.1 bar. Potassium formate is the only stoichiometric reagent, acting as a mildly basic nucleophile and a reservoir of CO. The substoichiometric CO could be delivered to the reaction from an acyl-Pd(II) precatalyst, which provides both the CO and an active catalyst, and thereby obviates the need for handling a toxic gas.

N-acylaminophenylcyclopropanes in reaction with nitrous acid generated in situ

The reaction of N-acylaminophenylcyclopropanes with HNO2 proceeds regioselectively with introduction of an N=O fragment into the three-membered ring and formation of the corresponding Δ2-isoxazolines. For ortho-substituted N-acylaminophenylcyclopropanes side processes were observed, caused by the intramolecular participation of the N-acyl group in conversions of the carbenium ions formed on opening the cyclopropane ring under the action of the nitrosating reagent, and by direct insertion of the modified ortho substituent into the three-membered ring.

Copper-catalyzed aerobic oxidative synthesis of aromatic carboxylic acids

A simple, practical and efficient copper-catalyzed method for synthesis of aromatic carboxylic acids has been developed. The protocol uses inexpensive CuI/l-proline as the catalyst/ligand, and readily available aryl halides and malononitrile as the starting materials, and the corresponding aromatic carboxylic acids were obtained in moderate to good yields. The method is of tolerance towards functional groups in the substrates.

Application of plant allylpolyalkoxybenzenes in synthesis of antimitotic phenstatin analogues

Phenstatin and its derivatives with the modified ring A have been synthesized, using plant allylpolyalkoxybenzenes as a starting material. The targeted molecules were evaluated in a phenotypic sea urchin embryo assay for antiproliferative activity. It was found that phenstatin ring A modifications yielded antimitotic compounds. The most effective myristicin derivative 7d (combretastatin A-2 analogue) was determined to be ca. 10 times more potent than phenstatin, displaying antimitotic tubulin-destabilizing activity at the same concentration range as combretastatins. In contrast to combretastatins, 7d featured the steric stability with potential for further design as anticancer agent.