134040-23-6

Basic information

• Product Name: Benzene, 1-ethoxy-4-(2-nitro-1-propenyl)-, (E)- (9CI)
• Synonyms: Benzene, 1-ethoxy-4-(2-nitro-1-propenyl)-, (E)- (9CI);1-ethoxy-4-[(E)-2-nitroprop-1-enyl]benzene
• CAS NO: 134040-23-6
• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.22582
• Product Categories: ETHOXY
• Mol File: 134040-23-6.mol

Chemical Properties

• Boiling Point: 335.1±17.0 °C(Predicted)
• Appearance: /
• Density: 1.129±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Benzene, 1-ethoxy-4-(2-nitro-1-propenyl)-, (E)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-ethoxy-4-(2-nitro-1-propenyl)-, (E)- (9CI)(134040-23-6)
• EPA Substance Registry System: Benzene, 1-ethoxy-4-(2-nitro-1-propenyl)-, (E)- (9CI)(134040-23-6)

Safety Data

• Hazardous Substances Data: 134040-23-6(Hazardous Substances Data)

Upstream product

• 79-24-3 Nitroethane 
• 10031-82-0 4-ethoxybenzaldehyde 

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.

Ethylenediamine: A highly effective catalyst for one-pot synthesis of aryl nitroalkenes via henry reaction and dehydration

Ethylenediamine (H2NCH2CH2NH2) was found to be a highly effective catalyst for the condensation of aryl aldehydes with nitromethane (or nitroethane). When 1%-2% (mol%) of ethylenediamine was used as the catalyst, the one-pot reaction of aryl aldehydes with nitromethane (or nitroethane) by refluxing for 3-10 h efficiently afforded various arylnitroalkenes 1a-1y in 85%-97% yields. Ethylenediamine (H 2NCH2CH2NH2) was found to be a highly effective catalyst for the condensation of aryl aldehydes with nitromethane (or nitroethane). When 1-2 mol% of ethylenediamine was used as the catalyst, the one-pot reaction of aryl aldehydes with nitromethane (or nitroethane) by refluxing for 3-10 h efficiently afforded various aryl nitroalkenes 1a-1y in 85%-97% yields. Copyright