155988-36-6

Basic information

• Product Name: 1-(3-CHLOROPHENYL)-2-NITROPROPENE
• Synonyms: 1-(3-CHLOROPHENYL)-2-NITROPROPENE;3'-CHLORO-BETA-METHYL-BETA-NITROSTYRENE
• CAS NO: 155988-36-6
• Molecular Formula: C₉H₈ClNO₂
• Molecular Weight: 197.62
• Product Categories: Propanes/propenes
• Mol File: 155988-36-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 304.788°C at 760 mmHg
• Flash Point: 138.131°C
• Appearance: /
• Density: 1.275g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.599
• CAS DataBase Reference: 1-(3-CHLOROPHENYL)-2-NITROPROPENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-CHLOROPHENYL)-2-NITROPROPENE(155988-36-6)
• EPA Substance Registry System: 1-(3-CHLOROPHENYL)-2-NITROPROPENE(155988-36-6)

Safety Data

• Hazardous Substances Data: 155988-36-6(Hazardous Substances Data)

Usage

General Description

1-(3-Chlorophenyl)-2-nitropropene is an organic chemical compound with the molecular formula C9H8ClNO2. 1-(3-CHLOROPHENYL)-2-NITROPROPENE is a yellow solid at room temperature and is often used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. It is important to handle this compound with caution as it is potentially toxic and may cause irritation to the skin and eyes upon contact. Additionally, 1-(3-Chlorophenyl)-2-nitropropene is known to be a reactive compound and should be stored and handled in a well-ventilated area to prevent any adverse reactions.

InChI:InChI=1/C9H8ClNO2/c1-7(11(12)13)5-8-3-2-4-9(10)6-8/h2-6H,1H3/b7-5+

Upstream product

• 79-24-3 Nitroethane 
• 587-04-2 m-Chlorobenzaldehyde 

Downstream Products

• 623177-14-0 7-chloro-2-methyl-1H-indole 
• 1075-35-0 5-chloro-2-methylindole 
• 1453201-17-6 (R)-1-chloro-3-(2-nitropropyl)benzene 
• 1618668-91-9 (S)-1-chloro-3-(2-nitropropyl)benzene 
• 29865-56-3 1-(3'-chlorophenyl)-2-nitropropane 
• 1426079-97-1 2-(3-chlorophenyl)-3-methylimidazo[1,2-a]pyridine 

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.

Enantioselective hydrogenation of α,β-disubstituted nitroalkenes

The first highly chemo- and enantioselective hydrogenation of α,β-disubstituted nitroalkenes was accomplished with rhodium/JosiPhos-J2 as a catalyst, with the yield and enantioselectivity of up to 95% and 94%, respectively. The α-chiral nitroalkanes will provide an entry to valuable chiral amphetamines which are otherwise not so easily accessed. This journal is the Partner Organisations 2014.