86255-45-0

Basic information

• Product Name: 1,2,4-trimethoxy-5-[(E)-2-nitroethenyl]benzene
• Synonyms: 1,2,4-Trimethoxy-5-[(E)-2-nitrovinyl]benzene; Benzene, 1,2,4-trimethoxy-5-[(E)-2-nitroethenyl]-
• CAS NO: 86255-45-0
• Molecular Formula: C₁₁H₁₃NO₅
• Molecular Weight: 239.2246
• Mol File: 86255-45-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 391.6°C at 760 mmHg
• Flash Point: 177.7°C
• Density: 1.203g/cm³
• Vapor Pressure: 5.48E-06mmHg at 25°C
• Refractive Index: 1.552
• CAS DataBase Reference: 1,2,4-trimethoxy-5-[(E)-2-nitroethenyl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4-trimethoxy-5-[(E)-2-nitroethenyl]benzene(86255-45-0)
• EPA Substance Registry System: 1,2,4-trimethoxy-5-[(E)-2-nitroethenyl]benzene(86255-45-0)

Safety Data

• Hazardous Substances Data: 86255-45-0(Hazardous Substances Data)

Usage

Appearance

Yellow, crystalline solid

Usage

Production of dyes, pigments, and other organic chemicals

Classification

Nitroalkene (contains both nitro and alkene functional groups)

Aromatic nature

Presence of a benzene ring

Physical state

Solid

Safety precautions

Handle and store under controlled conditions to prevent irritation and harm to skin, eyes, and respiratory system

Handling

Follow all recommended safety precautions during handling and use

Upstream product

• 75-52-5 nitromethane 
• 4460-86-0 asaraldehyde 
• 79-24-3 Nitroethane 
• 490-64-2 asaronic acid 

Downstream Products

• 15394-83-9 1-(2,4,5-trimethoxyphenyl)-2-aminoethane 
• 82698-30-4 1,2,4-Trimethoxy-5-(2-nitro-ethyl)-benzene 
• 38411-82-4 2-(2-amino-ethyl)-5-methoxy-hydroquinone 
• 88440-97-5 2-methoxy-5-<2-<(tert-butoxycarbonyl)amino>ethyl>-p-quinone 
• 88440-98-6 1-(2,5-dihydroxy-4-methoxyphenyl)-2-<(tert-butoxycarbonyl)amino>ethane 
• 88440-96-4 1-(2,4,5-trimethoxyphenyl)-2-<(tert-butoxycarbonyl)amino>ethane 

Relevant articles and documents

Synthesis, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in Burkitt’s lymphoma

Background: Cancers of the lymphatic cells (lymphomas) account for approximately 12% of malignant diseases worldwide. The nitrostyrene scaffold is identified as a lead target structure for the development of particularly effective compounds targeting Burkitt’s lymphoma (BL). Objectives: The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt’s lymphoma (BL). Methods: A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions. Single crystal X-Ray analysis confirmed the E configuration for six examples of these novel structures. A number of nitrostyrene-related compounds were also investigated including 1,3-bis(aryl)-2-nitropropenes together with heterocyclic scaffolds containing the nitrovinyl pharmacophore such as 3-nitro-2-phenyl-2H-chromenes. The antiproliferative activities of the compounds were evaluated using the BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant) to establish preliminary structure-activity relationships. Results: Lead compounds with optimized nitrostyrene scaffolds and 3-nitro-2-phenyl-2Hchromene structures were successfully established with typical IC50 values of 0.45 μM and 0.47 μM in MUTU-1 cells and 1.41 μM and 1.92 μM, respectively, in DG-75 cells. The mechanism of cell death was identified as apoptotic and the lead compound was found to elicit comparable apoptotic effects to Taxol in Burkitt’s lymphoma cell lines MUTU-1 and DG-75. Conclusion: This class of pharmaceutically active compounds with potential for the treatment of Burkitt’s lymphoma suggest a potential role for nitrostyrene based agents in chemotherapy.

Synthesis and biological evaluation of N-acetyl-β-aryl-1,2-didehydroethylamines as new HIV-1 RT inhibitors in vitro

A variety of N-acetyl-β-aryl-1,2-didehydroethylamines were synthesized by direct reduction-acetylation of β-aryl-nitroolefins and assayed as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) for the first time. Compound 7a exhibited a TI value of >13.2 with CC50 value of >0.787 mM in C8166 cells. This structure-activity relationship (SAR) study provided a new lead for design and discovery of more potent and selective analogues act as NNRTIs.