29559-25-9

Basic information

• Product Name: Benzene, 1-bromo-4-(nitromethyl)-
• Synonyms: 1-bromo-4-(nitromethyl)benzene;1-bromo-4-nitromethyl-benzene;4-bromophenylnitromethane;1-Brom-4-nitromethyl-benzol
• CAS NO: 29559-25-9
• Molecular Formula: C7H6BrNO2
• Molecular Weight: 216.034
• Mol File: 29559-25-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 295.6±15.0 °C(Predicted)
• Density: 1.603±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Benzene, 1-bromo-4-(nitromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-bromo-4-(nitromethyl)-(29559-25-9)
• EPA Substance Registry System: Benzene, 1-bromo-4-(nitromethyl)-(29559-25-9)

Safety Data

• Hazardous Substances Data: 29559-25-9(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 92430-66-5 2-(4-bromo-phenyl)-2-nitro-indan-1,3-dione 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 108-86-1 bromobenzene 
• 563-70-2 bromonitromethane 
• 1122-91-4 4-bromo-benzaldehyde 
• 25062-46-8 4-bromobenzaldehyde oxime 

Downstream Products

• 53847-52-2 3-(4-bromo-phenyl)-isoxazole-4,5-dicarboxylic acid dimethyl ester 
• 1122-91-4 4-bromo-benzaldehyde 

Relevant articles and documents

Organocatalytic, diastereo- and enantioselective synthesis of nonsymmetric cis -stilbene diamines: A platform for the preparation of single-enantiomer cis -imidazolines for protein-protein inhibition

The finding by scientists at Hoffmann-La Roche that cis-imidazolines could disrupt the protein-protein interaction between p53 and MDM2, thereby inducing apoptosis in cancer cells, raised considerable interest in this scaffold over the past decade. Initial routes to these small molecules (i.e., Nutlin-3) provided only the racemic form, with enantiomers being enriched by chromatographic separation using high-pressure liquid chromatography (HPLC) and a chiral stationary phase. Reported here is the first application of an enantioselective aza-Henry approach to nonsymmetric cis-stilbene diamines and cis-imidazolines. Two novel mono(amidine) organocatalysts (MAM) were discovered to provide high levels of enantioselection (>95% ee) across a broad range of substrate combinations. Furthermore, the versatility of the aza-Henry strategy for preparing nonsymmetric cis-imidazolines is illustrated by a comparison of the roles of aryl nitromethane and aryl aldimine in the key step, which revealed unique substrate electronic effects providing direction for aza-Henry substrate-catalyst matching. This method was used to prepare highly substituted cis-4,5-diaryl imidazolines that project unique aromatic rings, and these were evaluated for MDM2-p53 inhibition in a fluorescence polarization assay. The diversification of access to cis-stilbene diamine-derived imidazolines provided by this platform should streamline their further development as chemical tools for disrupting protein-protein interactions.