5438-41-5

Basic information

• Product Name: 5-(2-NITROPROP-1-ENYL)-1,3-BENZODIOXOLE
• Synonyms: 5-(2-NITROPROP-1-ENYL)-1,3-BENZODIOXOLE;1-(3',4'-METHYLENEDIOXYPHENYL)-2-NITRO-1-PROPENE;1-(3,4-METHYLENEDIOXYPHENYL) 2-NITROPROPENE;1-(3,4-Methylenedioxyphenyl)-2-nitroprop-1-ene;5-(2-Nitroprop-1-enyl)benzo[d][1,3]dioxole;5-(2-Nitroprop-1-en-1-yl)benzo[d][1,3]dioxole;1,3-Benzodioxole,5-(2-nitro-1-propen-1-yl)-;5-[(1E)-2-nitroprop-1-en-1-yl]-1,3-benzodioxole
• CAS NO: 5438-41-5
• Molecular Formula: C₁₀H₉NO₄
• Molecular Weight: 207.18
• Product Categories: Propanes/propenes
• Mol File: 5438-41-5.mol

Chemical Properties

• Melting Point: 94-96°C
• Boiling Point: 336.7 °C at 760 mmHg
• Flash Point: 160.7 °C
• Appearance: /
• Density: 1.343 g/cm³
• Vapor Pressure: 0.000215mmHg at 25°C
• Refractive Index: 1.62
• CAS DataBase Reference: 5-(2-NITROPROP-1-ENYL)-1,3-BENZODIOXOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-NITROPROP-1-ENYL)-1,3-BENZODIOXOLE(5438-41-5)
• EPA Substance Registry System: 5-(2-NITROPROP-1-ENYL)-1,3-BENZODIOXOLE(5438-41-5)

Safety Data

• Statements: 23/24/25-36/37/38
• Safety Statements: 23-24/25
• Hazardous Substances Data: 5438-41-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-(2-NITROPROP-1-ENYL)-1,3-BENZODIOXOLE is used as a research chemical for its inhibitory properties on hepatic microsomal enzyme function in mice. This application is crucial in the development of new drugs and therapies, as it can help understand the metabolic pathways and potential interactions with other compounds.
Used in Chemical Research:
As a byproduct of 3,4-Methylenedioxy Methamphetamine (M303985), 5-(2-NITROPROP-1-ENYL)-1,3-BENZODIOXOLE can be utilized in chemical research to explore its properties, reactivity, and potential applications in various chemical processes and reactions.
Used in Toxicology Studies:
Due to its origin from a psychoactive substance, 5-(2-NITROPROP-1-ENYL)-1,3-BENZODIOXOLE can be employed in toxicology studies to investigate the effects of its parent compound and related substances on biological systems, potentially leading to a better understanding of their mechanisms of action and safety profiles.
Used in Environmental Monitoring:
The chemical properties of 5-(2-NITROPROP-1-ENYL)-1,3-BENZODIOXOLE, including its solid state and color, make it a candidate for environmental monitoring applications, where it could be used to detect or quantify the presence of specific contaminants or pollutants in various samples.
Used in Material Science:
The unique properties of 5-(2-NITROPROP-1-ENYL)-1,3-BENZODIOXOLE may also find applications in material science, where it could be used to develop new materials with specific characteristics, such as improved stability, reactivity, or selectivity in various chemical processes.

InChI:InChI=1/C10H9NO4/c1-7(11(12)13)4-8-2-3-9-10(5-8)15-6-14-9/h2-5H,6H2,1H3/b7-4+

Upstream product

• 79-24-3 Nitroethane 
• 120-57-0 piperonal 
• 148527-36-0 acetic acid-(1-benzo[1,3]dioxol-5-yl-2-nitro-propyl ester) 
• 509-14-8 tetranitromethane 
• 120-58-1 isosafrole 
• 2620-50-0 1,3-benzodioxol-5-ylmethyl amine 
• 4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone 
• 36462-33-6 1-Benzo[1,3]dioxol-5-yl-2-nitro-propan-1-ol 

Downstream Products

• 4764-17-4 3,4-methylenedioxyamphetamine 
• 4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone 
• 136056-99-0 benzo[1,3]dioxol-5-yl-acetone oxime 
• 42542-10-9 3,4-methylenedioxymethamphetamine 
• 154148-22-8 N-(2-benzo[1,3]dioxol-5-yl-1-methylethyl)-N-methylformamide 
• 36209-71-9 N-[1-methyl-2-(3,4-methylenedioxyphenyl)ethyl]acetamide 
• 14089-52-2 3,4-methylenedioxyethylamphetamine 
• 1449522-77-3 4-benzo[1,3]dioxol-5-yl-5-methyl-2-phenyl-1H-imidazole 
• 87095-03-2 5-(2-nitropropyl)benzo[d][1,3]dioxole 
• 4720-68-7 4,5-methylenedioxy-2-hydroxybenzaldehyde 
• 6974-61-4 β-oxy-α-(3',4'-methylenedioxyphenyl)propane 

Relevant articles and documents

Synthesis, antimicrobial study, and molecular docking simulation of 3,4-dimethoxy-β-nitrostyrene derivatives as candidate ptp1b inhibitor

A derivative series of 3,4-dimethoxy-β-nitrostyrene was synthesized through nitroaldol reaction, including a new compound of 3,4-ethylenedioxy-β-bromo-β-nitrostyrene. The antimicrobial activity effect of 3,4-alkyloxy modification of β-nitrostyrene was investigated. A molecular docking study was also performed to obtain information about their interactions with protein tyrosine phosphatase 1B (PTP1B). The active residues of cysteine-215 and arginine-221 of PTP1B play a key role in signaling pathways that regulate various microorganism cell functions. It also acts as a negative regulator in signaling pathways of insulin that are involved in type 2 diabetes and other metabolic diseases. These derivatives exhibited potential antifungal activity. The studied compounds were also had potential as fragments to be PTP1B inhibitors by interacting with serine-216 and arginine-221 residues, according to their molecular docking. 3,4-Ethylenedioxy-β-methyl-β-nitrostyrene was the most successful potential candidate as a PTP1B inhibitor. However, further research is needed to investigate their potential for medicinal use.

Copper-Catalyzed Propargylation of Nitroalkanes

Using a commercially available, inexpensive, and abundant copper catalyst system, an efficient α-functionalization of nitroalkanes with propargyl bromides is now established. This mild and robust method is highly functional group tolerant and provides straightforward access to complex secondary and tertiary homopropargylic nitroalkanes. Moreover, the utility of these α-propargylated nitroalkanes is demonstrated through downstream functionalization to biologically relevant, five-membered N-heterocycles such as pyrroles and 2-pyrrolines.

Substrate promiscuity of ortho-naphthoquinone catalyst: Catalytic aerobic amine oxidation protocols to deaminative cross-coupling and n-nitrosation

ortho-Naphthoquinone-based organocatalysts have been identified as versatile aerobic oxidation catalysts. Primary amines were readily cross-coupled with primary nitroalkanes via deaminative pathway to give nitroalkene derivatives in good to excellent yields. Secondary and tertiary amines were inert to ortho-naphthoquinone catalysts; however, secondary nitroalkanes were readily converted by ortho-naphthoquinone catalysts to the corresponding nitrite species that in situ oxidized the amines to the corresponding N-nitroso compounds. Without using harsh oxidants in a stoichiometric amount, the present catalytic aerobic oxidation protocol utilizes the substrate promiscuity feature to provide a facile access to amine oxidation products under mild reaction conditions.

Inhibition of LDL oxidation and inflammasome assembly by nitroaliphatic derivatives. Potential use as anti-inflammatory and anti-atherogenic agents

We have previously shown the antioxidant and anti-inflammatory properties of several para-substituted arylnitroalkenes. Since oxidative stress and inflammation are key processes that drive the initiation and progression of atherosclerosis, in the present work the antioxidant, anti-inflammatory and anti-atherogenic properties of an extended library of aryl-nitroaliphatic derivatives, including several newly designed nitroalkanes, was explored. The antioxidant capacity of the nitroaliphatic compounds, measured using the oxygen radical absorbance capacity assay (ORAC) showed that the p-methylthiophenyl-derivatives were about three times more effective than Trolox to prevent fluorescein oxidation, independently of the presence or the absence of the double bond next to the nitro group. The peroxyl radical scavenger capacity of the p-dimethylaminophenyl-derivatives was even higher, being the reduced form of these compounds even more active. In fact, while the antioxidant capacity of 1-dimethylamino-4-(2-nitro-1Z-ethenyl)benzene and 1-dimethylamino-4-(2-nitro-1Z-propenyl)benzene was 4.2 ± 0.1 and 5.4 ± 0.1 Trolox Eq/mol, respectively; ORAC values obtained with the ethyl and the propyl derivatives were 10 ± 1 and 13 ± 2 Trolox Eq/mol, respectively. The p-dimethylamino-derivatives, especially the nitroalkanes, were also able to prevent LDL oxidation mediated by peroxyl radicals. Oxygen consumption due to the oxidation of fatty acids was delayed in the presence of the dimethylamino substituted compounds, only the alkanes interrupted the chain of lipid oxidations decreasing the rate of oxygen consumption. Although the formation of foam cells in the presence of oxidized-LDL (oxLDL) remained unaffected, the molecules containing the dimethylamino moiety were able to decrease the expression of IL-1β in LPS/INF-γ challenged macrophages.

ANTIMICROBIAL AND RADIOPROTECTIVE COMPOUNDS

The present invention relates to a method of treatment and/or prophylaxis of a microbial infection, comprising the step of administering an effective amount of a compound of formula (I), in which X and Y are either the same or different and selected from a heteroatom; is a double or single bond depending on the heteroatoms X and Y; R1 to R5 are either the same or different and selected from hydrogen or a non-deleterious substituent; and R6 and R7 are either the same or different and selected from hydrogen and a non-deleterious substituent or one of R6 and R7 are absent when there is a double bond present, pharmaceutically acceptable salts or derivatives, pro-drugs, tautomers and/or isomers thereof. The present invention also relates to a method for protecting a subject from radiation damage, a method of cancer radiotherapy and use as an antimicrobial or radioprotective agent of the compound of formula (I) defined above. Some of the compounds of formula (I) are novel and are also described in the present invention, together with pharmaceutical or veterinary compositions containing them.

Arylnitroalkenes as scavengers of macrophage-generated oxidants

Oxygen and nitrogen derived molecules mediated oxidation and nitration have been involved in several pathological conditions. Conversely, nitric oxide and hydrogen peroxide are important signalization intermediates, whose concentrations are tightly regula

One-pot solid phase synthesis of (E)-nitroalkenes

An efficient one-pot protocol for the synthesis of (E)-nitroalkenes by reaction of aldehydes and nitroalkanes in the presence of polymer-bound triphenylphosphine, iodine and imidazole is described. Although the reaction works with similar efficiency with triphenylphosphine and its polymer-bound version, easy removal of the unwanted polymer-bound triphenylphosphine oxide and its recovery as triphenylphosphine provide the edge for practical application of the method.

Palladium-catalyzed synthesis of substituted nitroolefins

A one-pot protocol toward several substituted nitroolefins 4 and 6 starting with substituted acetones 2 and 5 was described. A facile process was carried out for the triflation of substituted acetones 2 and 5 with triflic anhydride (Tf2O) under the basic condition (Cs2CO3) and then palladium-catalyzed cross-coupling of enol triflates 3 with NaNO 2 and BINAP in the presence of phase-transfer reagents (n-Bu 4NBr) under the refluxing 1,2-dimethoxyethane (DME) in acceptable yields.

METHOD OF TREATING SCEDOSPORIUM SPP. INFECTION

The present invention provides a method of treatment of Scedosporium spp. infection in an animal comprising the step of administering to the infected animal an effective amount of a compound of formula I or a pharmaceutically-acceptable salt thereof

Exploring nitrostyrene as a scaffold for a new class a of monoamine oxidase inhibitors

With the ultimate purpose of finding out the structural features that are relevant for MAO inhibitory activity and selectivity towards MAO-B isoform, a series of compounds encompassing a β-nitrostyrene moiety was designed and the in vitro inhibitory activity was evaluated. In the present work, we report the synthesis and the pharmacological evaluation of a series of functionalized derivatives of β-methyl-β-nitrostyrene with distinct substitution patterns in the phenyl ring, namely hydroxyl, methoxy, benzyloxy and methylenedioxy. All the studied compounds were substituted in meta and para positions of the phenyl ring related to the nitrovinyl side chain. The synthesized compounds were evaluated towards both human MAO isoforms, displaying some of them activities in the low micromolar range. Particularly compound 6 (a methylenedioxy derivative) exhibits high potency and selectivity towards MAO-B.