2620-44-2

Basic information

• Product Name: 1,2-(Methylenedioxy)-4-nitrobenzene
• Synonyms: 5-NITRO-1,3-BENZODIOXOLE;1,2-(METHYLENEDIOXY)-4-NITROBENZENE;3,4-METHYLENEDIOXYNITROBENZENE;3,4-(Methylenedioxy)-1-nitrobenzene;5-nitro-3-benzodioxole;5-Nitrobenzodioxole;Benzene, 1,2-(methylenedioxy)-4-nitro-;Methylenedioxynitrobenzene
• CAS NO: 2620-44-2
• Molecular Formula: C₇H₅NO₄
• Molecular Weight: 167.12
• EINECS: 220-055-6
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Aromatic Hydrocarbons (substituted) & Derivatives;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 2620-44-2.mol

Chemical Properties

• Melting Point: 146-148 °C(lit.)
• Boiling Point: 295.67°C (rough estimate)
• Flash Point: 289 °F
• Appearance: yellow fine crystalline powder
• Density: 1.5216 (rough estimate)
• Vapor Pressure: 0.00734mmHg at 25°C
• Refractive Index: 1.6280 (estimate)
• Solubility: acetone: soluble2.5%, clear to slightly hazy, yellow
• BRN: 169063
• CAS DataBase Reference: 1,2-(Methylenedioxy)-4-nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-(Methylenedioxy)-4-nitrobenzene(2620-44-2)
• EPA Substance Registry System: 1,2-(Methylenedioxy)-4-nitrobenzene(2620-44-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22
• Safety Statements: 36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 2620-44-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1,2-(Methylenedioxy)-4-nitrobenzene is used as a key intermediate in the chemical synthesis industry for the production of various organic compounds. Its unique structure and reactivity make it a valuable building block for creating a wide range of molecules with diverse applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,2-(Methylenedioxy)-4-nitrobenzene is used as a starting material for the synthesis of various drugs and drug candidates. Its versatile chemical properties allow for the development of new therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Dye and Pigment Industry:
1,2-(Methylenedioxy)-4-nitrobenzene is also utilized in the dye and pigment industry as a precursor for the production of various colorants. Its chemical structure contributes to the development of dyes and pigments with specific color properties, which are essential for various applications, including textiles, plastics, and printing inks.
Used in Material Science:
In the field of material science, 1,2-(Methylenedioxy)-4-nitrobenzene is employed in the development of novel materials with specific properties. Its incorporation into polymers and other materials can lead to enhanced performance characteristics, such as improved thermal stability, mechanical strength, or electrical conductivity, depending on the desired application.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 28, p. 625, 1991 DOI: 10.1002/jhet.5570280316Tetrahedron, 64, p. 4999, 2008 DOI: 10.1016/j.tet.2008.03.085

InChI:InChI=1/C7H5NO4/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3H,4H2

Upstream product

• 274-09-9 Methylenedioxybenzene 
• 120-57-0 piperonal 
• 94-53-1 Piperonylic acid 
• 712-97-0 6-nitro-1,3-benzodioxole-5-carbaldehyde 
• 75-11-6 diiodomethane 
• 3316-09-4 1,2-dihydroxy-4-nitrobenzene 
• 14268-66-7 benzo[1,3]dioxolo-5-ylamine 
• 509-14-8 tetranitromethane 
• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 716-32-5 6-nitrobenzo[d][1,3]dioxole-5-carboxylic acid 
• 133-03-9 sesamin 
• 133-03-9 sesamin 

Downstream Products

• 636-93-1 5-nitroguaiacol 
• 7260-32-4 2-ethoxy-5-nitro-phenol 
• 3316-09-4 1,2-dihydroxy-4-nitrobenzene 
• 7748-59-6 5,6-dinitro-benzo[1,3]dioxole 
• 14268-66-7 benzo[1,3]dioxolo-5-ylamine 
• 145101-98-0 2-(propylthio)-5-nitrophenol 
• 39835-14-8 2-hydroxy-4-nitro-benzonitrile 
• 130400-94-1 3-hydroxy-4-isopropoxynitrobenzene 
• 75437-90-0 4-Nitro-2-phenoxymethoxy-phenol 
• 2242-35-5 2-benzyloxy-5-nitrophenol 
• 158719-75-6 2-(2-bromophenylthiomethoxy)-4-nitrophenol 
• 146310-47-6 4-ethylthio-3-hydroxynitrobenzene 
• 108950-12-5 2-benzo[1,3]dioxol-5-ylamino-4-nitro-benzoic acid 
• 146853-20-5 5-Nitrosobenzo[d][1,3]dioxole 

Relevant articles and documents

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.

N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- And Heteroarylboronic Acids

Photocatalytic and metal-free protocols to access various aromatic and heteroaromatic nitro compounds through ipso-nitration of readily available boronic acid derivatives were developed using non-metal-based, bench-stable, and recyclable nitrating reagents. These methods are operationally simple, mild, regioselective, and possess excellent functional group compatibility, delivering desired products in up to 99% yield.

Regioselective Functionalization of 9,9-Dimethyl-9-silafluorenes by Borylation, Bromination, and Nitration

Despite the utility of 9-silafluorenes as functional materials and as building blocks, methods for efficient functionalization of their backbone are rare, probably because of the presence of easily cleavable C-Si bonds. Although controlling the regioselectivity of iridium-catalyzed direct borylation of C-H bonds is difficult, we found that bromination and nitration of 2-methoxy-9-silafluorene under mild conditions occurred predominantly at the electron-rich position. The resulting product having methoxy and bromo groups can be utilized as a building block for the synthesis of unsymmetrically substituted 9-silafluorene-containing π-conjugated molecules.

Regioselective Functionalization of 9,9-Dimethyl-9-silafluorenes by Borylation, Bromination, and Nitration

Despite the utility of 9-silafluorenes as functional materials and as building blocks, methods for efficient functionalization of their backbone are rare, probably because of the presence of easily cleavable C-Si bonds. Although controlling the regioselectivity of iridium-catalyzed direct borylation of C-H bonds is difficult, we found that bromination and nitration of 2-methoxy-9-silafluorene under mild conditions occurred predominantly at the electron-rich position. The resulting product having methoxy and bromo groups can be utilized as a building block for the synthesis of unsymmetrically substituted 9-silafluorene-containing ?-conjugated molecules.

Method of using I2O5/NaNO2 to nitrify electron-rich aromatic compounds

The invention belongs to the field of organic chemical medicine, and especially relates to a method of using I2O5/NaNO2 to nitrify electron-rich aromatic compounds. According to the method, electron-rich aromatic compounds are taken as the raw material; sodium nitrite is taken as a nitrifying agent; at the same time, iodine pentoxide is added and taken as an oxidizing agent; then a proper amount of a solvent is added to carry out reactions for a while at a temperature of 10 to 25 DEG C under stirring; after reactions, a sodium thiosulfate solution is added to quench the reactions; the reactionsystem is extracted for three times by ethyl acetate; then the organic phases are merged and dried by anhydrous sodium sulfate; filtering is carried out, the solvent is evaporated maximally; silica gel is used to carry out adsorption, and the target product is obtained through column chromatography separation. The goal of converting electron-rich aromatic compounds into corresponding nitrification products under mild conditions is realized.

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.

Class of large ring heterocyclic compound restraining HCV and manufacturing and uses thereof

The invention relates to a class of compounds that inhibit HCV. The compounds are represented by Formula A. The invention also relates to preparation and pharmaceutical use of the compounds.

Nucleophilic Nitration of Arynes by Sodium Nitrite and its Multicomponent Reaction Leading to Double-Functionalized Arenes

An unusual nucleophilic nitration of arynes by NaNO2 in the presence of water has been developed, and the concept was further demonstrated to accomplish a double functionalization of arynes using a multicomponent reaction protocol to synthesize pharmaceutically important (2-nitrophenyl)methanol derivatives. Such substitution ortho to -NO2 is difficult by other means. The reaction conditions are mild and avoid the use of strong acids, expensive transition metal catalysts, and additives.

3,4-methylenedioxy aniline preparation method

A 3,4-methylenedioxy aniline preparation method applied to the field of chemosynthesis comprises the following steps: (1) adding dilute nitric acid into a reaction vessel for heating; (2) dropwise adding 1,2-methylenedioxy benzene into the reaction vessel slowly, carrying out intense stirring during the dropwise adding, and carrying out heat preservation after the dropwise adding is finished; (3) carrying out cooling and filtration to obtain a wet product of 3,4-methylenedioxy nitrobenzene, carrying out washing with purified water till the pH value of the wet product reaches 7, and carrying out vacuum drying to obtain 3,4-methylenedioxy nitrobenzene; (4) putting 3,4-methylenedioxy nitrobenzene, a nickel catalyst and one or more reaction solvents into a high-pressure reaction kettle for heating, injecting hydrogen, filtering out the nickel catalyst after the reaction is finished, carrying out high vacuum distillation after a low-boiling-point substance is removed through reduced pressure distillation, and collecting fractions to obtain 3,4-methylenedioxy aniline. The 3,4-methylenedioxy aniline preparation method has the advantages that nitrification reduction and hydrogenation reduction processes are adopted; less waste water, waste gas and solid waste are treated; the selectivity is high; the product treatment is easy; the product yield and the product quality are high; nitric acid, the hydrogenation catalyst and the hydrogenation organic solvents can be recovered for direct application.

Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship

In our earlier study, we have reported that a phenolic compound 2-hydroxy-4-methoxybenzaldehyde from Janakia arayalpatra root extract was active against Viper and Cobra envenomations. Based on the structure of this natural product, libraries of synthetic structurally variant phenolic compounds were studied through molecular docking on the venom protein. To validate the activity of eight selected compounds, we have tested them in in vivo and in vitro models. The compound 21 (2-hydroxy-3-methoxy benzaldehyde), 22 (2-hydroxy-4-methoxybenzaldehyde) and 35 (2-hydroxy-3-methoxybenzylalcohol) were found to be active against venom-induced pathophysiological changes. The compounds 20, 15 and 35 displayed maximum anti-hemorrhagic, anti-lethal and PLA2 inhibitory activity respectively. In terms of SAR, the presence of a formyl group in conjunction with a phenolic group was seen as a significant contributor towards increasing the antivenom activity. The above observations confirmed the anti-venom activity of the phenolic compounds which needs to be further investigated for the development of new anti-snake venom leads.