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
• Article Data: 19

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

Chemical Properties

Yellow Solid

Uses

A byproduct of 3,4-Methylenedioxy Methamphetamine (M303985). Inhibitor of the hepatic microsomal enxzyme function in mice.

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

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 
• 4720-68-7 4,5-methylenedioxy-2-hydroxybenzaldehyde 
• 87095-03-2 5-(2-nitropropyl)benzo[d][1,3]dioxole 
• 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 
• 6974-61-4 β-oxy-α-(3',4'-methylenedioxyphenyl)propane 
• 1449522-77-3 4-benzo[1,3]dioxol-5-yl-5-methyl-2-phenyl-1H-imidazole 

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.

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.

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.