16498-20-7

Usage

Uses

Used in Organic Synthesis:
2,3-Dihydro-6-nitro-1,4-benzodioxin is used as a synthetic intermediate for the production of various organic compounds. Its unique structure and functional groups make it a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3-Dihydro-6-nitro-1,4-benzodioxin is used as a key intermediate in the synthesis of certain drugs. Its presence in the molecular structure can impart specific biological activities, making it an essential component in the development of new therapeutic agents.
Used in Agrochemical Industry:
2,3-Dihydro-6-nitro-1,4-benzodioxin is also utilized in the agrochemical industry for the synthesis of various pesticides and herbicides. Its incorporation into these compounds can enhance their effectiveness in controlling pests and weeds, contributing to increased crop yields and agricultural productivity.
Used in Specialty Chemicals:
In the specialty chemicals sector, 2,3-Dihydro-6-nitro-1,4-benzodioxin is employed in the production of dyes, pigments, and other colorants. Its chemical properties allow it to impart vibrant colors and improve the stability of these products, making it a valuable component in various applications.

Upstream product

• 493-09-4 benzo-1,4-dioxane 
• 3316-09-4 1,2-dihydroxy-4-nitrobenzene 
• 106-93-4 ethylene dibromide 
• 913178-39-9 3,4-ethylenedioxyphenyl(phenyl)methyl acetate 
• 20625-42-7 1-(3,4-ethylenedioxyphenyl)propan-1-ol 
• 108-24-7 acetic anhydride 
• 351342-79-5 3,4-ethylenedioxyphenyl(phenyl)methanol 
• 93637-87-7 2,3-dihydro-1,4-benzodioxin-6-yl(phenyl)methanone 
• 120-80-9 benzene-1,2-diol 
• 164014-95-3 2.3-dihydro-1,4-benzodioxin-6-ylboronic acid 
• 369-34-6 3,4-difluoronitrobenzene 
• 107-21-1 ethylene glycol 

Downstream Products

• 22013-33-8 6-amino-3,4-benzodioxane 
• 57356-48-6 6,7-dinitro-2,3-dihydrobenzo[1,4]dioxine 
• 59820-94-9 5,6-dinitro-2,3-dihydrobenzo[b][1,4]dioxine 
• 59820-95-0 5,7-dinitro-2,3-dihydro-benzo[1,4]dioxine 
• 42477-08-7 3-chloro-propionic acid-(2,3-dihydro-benzo[1,4]dioxin-6-ylamide) 
• 100254-21-5 N-ethyl-glycine-(2,3-dihydro-benzo[1,4]dioxin-6-ylamide) 
• 90609-94-2 N-(2,3-dihydro-1,4-benzodioxin-6-yl)methylamine 

Relevant academic research and scientific papers

Electrochemical Nitration with Nitrite

Aromatic nitration has tremendous importance in organic chemistry as nitroaromatic compounds serve as versatile building blocks. This study represents the electrochemical aromatic nitration with NBu4NO2, which serves a dual role as supporting electrolyte and as a safe, readily available, and easy-to-handle nitro source. Stoichiometric amounts of 1,1,1-3,3,3-hexafluoroisopropan-2-ol (HFIP) in MeCN significantly increase the yield by solvent control. The reaction mechanism is based on electrochemical oxidation of nitrite to NO2, which initiates the nitration reaction in a divided electrolysis cell with inexpensive graphite electrodes. Overall, the reaction is demonstrated for 20 examples with yields of up to 88 %. Scalability is demonstrated by a 13-fold scale-up.

Direct nitration method of electron-enriched aromatic hydrocarbons

The invention discloses a direct nitration method of electron-enriched aromatic hydrocarbons, and belongs to the field of organic synthesis. The direct nitration method is a novel green free radical nitration method; aromatic hydrocarbons are taken as raw materials, acetonitrile, dichloromethane, chloroform, or acetone is taken as a reaction solvent, at room temperature conditions, the raw materials and green nitration reagent tert-butyl nitrite (TBN) are subjected to free radical nitration so as to obtain nitro-aromatic compounds. According to the direct nitration method, no metal is adoptedin reaction, tert-butyl nitrite is directly adopted in nitration reaction. Electron-donating groups such as OMe are introduced, the electron density of aromatic compounds is increased, the nitration reaction possibility is increased. The using amount of tert-butyl nitrite is reduced; only a product and tert-butyl alcohol are generated, environment pollution is reduced. The direct nitration methodis promising in application prospect in the field of nitro-aromatic compound synthesis, green nitration is realized, and a novel idea is provided for large-scale industrialized nitro-aromatic compoundproduction.

Base-promoted nucleophilic fluoroarenes substitution of C–F bonds

With the use of KOH/DMSO as the superbase medium, the nucleophilic fluoroarene substitution for C–F bonds is presented. The transformation proceeds smoothly with the use of fluoroarenes bearing not only electron-withdrawing group, but also electron-donating group and a variety of nucleophiles such as alcohols, phenols, amines, amides and nitrogen-heterocyclic compounds. The double nucleophilic substitution using ortho-difluoroarenes and nucleophiles bearing ortho-dinucleophilic groups results in the formation of 2,3-dihydro-1,4-benzodioxins, dibenzo[b,e][1,4]dioxins and 10H-phenoxazines in moderate to good yields.

Benzodioxane group containing hole-transport material, preparation method therefor and application of hole-transport material

The invention discloses a benzodioxane group containing hole-transport material, a preparation method therefor and an application of the hole-transport material and belongs to the technical field of perovskite solar cells. The hole-transport material has a molecular structure represented by a formula shown in the description. The invention also discloses the preparation method for the hole-transport material and the application of the hole-transport material in perovskite solar cell devices. Simultaneously, the invention also discloses a perovskite solar cell device. According to the hole-transport material disclosed by the invention, different alkyl chains are introduced to a parent nucleus or side chain so as to improve solubility; by introducing diarylamine with a spatial three-dimensional form or a carbazole group, the crystallization of the material can be avoided, and then, the stability of the material is improved; and meanwhile, due to a spatial three-dimensional structure, the solubility of the material can be improved, and then, the film forming property is improved.

AMIDS SUBSTITUTED INDAZOLE DERIVATIVEES AS PLOY (ADP-RIBOSE) POLYMERASE INHIBITORS

The present invention relates to amide substituted indazoles and benzotriazoles which are inhibitors of the enzyme poly (ADP-ribose) polymerase (PARP), previously known as poly (ADP-ribose) synthase and poly (ADP-ribosyl) transferase. The compounds of the present invention are useful as mono-therapies in tumors with specific defects in DNA-repair pathways, as enhancers of certain DNA-damaging agents such as anticancer agents and radiotherapy, for reducing cell necrosis (in stroke and myocardial infarction), regulating inflammation and tissue injury, treating retroviral infections, and protecting against the toxicity of chemotherapy.

A novel transition metal free [bis-(trifluoroacetoxy)iodo]benzene (PIFA) mediated oxidative ipso nitration of organoboronic acids

A mild, convenient and transition metal free methodology for oxidative ipso nitration of diversely functionalized organoboronic acids, including heteroaryl- and alkylboronic acids, has been developed at ambient temperature using a combination of [bis-(trifluoroacetoxy)]iodobenzene (PIFA) - N-bromosuccinimide (NBS) and sodium nitrite as the nitro source. It is anticipated that the reaction proceeds through in situ generation of NO2 and O-centred organoboronic acid radicals followed by the formation of an O-N bond via combination of the said radicals. Finally transfer of the NO2 group to the aryl moiety occurs through 1,3-aryl migration to provide the nitroarenes.

Catalyst-free ipso-nitration of aryl boronic acids using bismuth nitrate

We report a catalyst-free ipso-nitration of aryl boronic acids using bismuth (III) nitrate as nitrating agent. Reaction proceeds in shorter reaction times with moderate to excellent yields. This method is operationally simple, regioselective, and possesses excellent functional group compatibility to synthesize nitroarenes.

Synthesis and spectral properties of 4-amino-and 4-acetylamino-N- arylnaphthalimides containing electron-donating groups in the N-aryl substituent

A method for the synthesis of N-aryl-substituted 4-amino-and 4-acetylaminonaphthalimide derivatives with mono-and dialkoxy groups or a 15-crown-5 moiety in the N-aryl substituent is described. The introduction of electron-donating alkoxy groups into the benzene ring of the N-aryl fragment results in fluorescence quenching of the naphthalimide chromophore, which is most pronounced in the spectra of N-acetyl derivatives. The photophysical properties of the synthesized 4-amino-and 4-acetylaminonaphthalimides depend on the solvent polarity and its specific solvating ability due to H-bonding. The crown-containing compounds are promising fluorescent chemosensors for metal cations. ; 2009 Springer Science+Business Media, Inc.

Synthesis of o-nitrosoacylbenzenes from o-nitrobenzyl alcohols and their derivatives

Nitration of substituted benzyl alcohols, as well as ethers and esters derived therefrom, with nitric acid in acetic anhydride was studied. The corresponding o-nitrobenzyl alcohols and their derivatives formed as the primary products are capable of being converted into o-nitrosoacylbenzenes by the action of acids. Pleiades Publishing, Inc., 2006.

Influence of the Heterocyclic Side Ring on Orientation During Nitrations of 1,2-Alkylenedioxy-annelated Benzenes and Their Mononitro Derivatives

Nitration of 1,2-alkylenedioxybenzenes 1 furnished the respective nitro derivatives 3 and 4 in the relative ratios: 4a:3a/100:trace, 4b:3b/98:2.4, 4c:3c/86:14, 4e:3e/91:9, 4f:3f/99:1.3.Nitration of 4 gave 5a:6a:8a/0:0:100, 5b:6b:8b/7.7:3.2:89, 5c:6c:8c/23:12:65, 5d:6d:8d/14:74:12, 5e:6e:8e/27:18:55 and 5f:6f:8f/23:7.0:70.Nitration of the isomeric 3 afforded the dinitroproducts 5, 6 and 7 in the following relative ratios: 5a:6a:7a/92:8:0, 5b:6b:7b/80:20:0, 5c:6c:7c/69:20:11, 5d:6d:7d/45:19:36, 5e:6e:7e/37:57:5.9 and 5f:6f:7f/64:36:0.Nitration of 3-nitro-1,2-dimethoxybenzene (9) furnished: 10:11/63:37.Orientation as a function of the h eterocyclic ring-size is discussed.