54737-45-0

Basic information

• Product Name: Benzene, 1-bromo-2-[(1E)-2-phenylethenyl]-
• CAS NO: 54737-45-0
• Molecular Formula: C14H11Br
• Molecular Weight: 259.145
• Mol File: 54737-45-0.mol
• Article Data: 39

Chemical Properties

• CAS DataBase Reference: Benzene, 1-bromo-2-[(1E)-2-phenylethenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-bromo-2-[(1E)-2-phenylethenyl]-(54737-45-0)
• EPA Substance Registry System: Benzene, 1-bromo-2-[(1E)-2-phenylethenyl]-(54737-45-0)

Safety Data

• Hazardous Substances Data: 54737-45-0(Hazardous Substances Data)

Upstream product

• 78602-27-4 1-(o-bromophenyl)-2-phenylethanol 
• 102-96-5 (2-nitroethenyl)benzene 
• 615-36-1 2-bromoaniline 
• 36901-75-4 (2-bromobenzyl)triphenylphosphonium bromide 
• 100-52-7 benzaldehyde 
• 65185-68-4 o-bromonitrostyrene 
• 94-36-0 dibenzoyl peroxide 
• 100-42-5 styrene 
• 2905-25-1 o-bromobenzenesulfonyl chloride 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 1486-28-8 diphenyl(methyl)phosphine 
• 21955-55-5 benzyl(methyl)diphenylphosphonium bromide 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 51958-51-1 1-bromophenanthrene 
• 103473-98-9 E-methyl 2-(2'-phenylethenyl)phenylglyoxalate 
• 1290029-64-9 trans-2-(N-phenylamino)stilbene 
• 41498-43-5 4-Phenanthrencarbaldehyd 
• 85-01-8 phenanthrene 

Relevant articles and documents

Wittig Olefination Using Phosphonium Ion-Pair Reagents Incorporating an Endogenous Base

Despite common perception, the use of strong bases in Wittig chemistry is utterly unnecessary: we report a series of novel ion-pair phosphonium carboxylate reagents which are essentially "storable ylides". These reagents are straightforwardly prepared in excellent yields, and their fluxional nature permits clean olefination of a broad range of aldehydes and even hemiacetals.

E, Z -Selectivity in the reductive cross-coupling of two benzaldehydes to stilbenes under substrate control

Unsymmetrical E- and Z-stilbenes can be synthesized from two differently substituted benzaldehydes in a MesP(TMS)Li-promoted reductive coupling sequence. Depending on the order of addition of the two coupling partners, the same olefin can be produced in either E- or Z-enriched form under identical reaction conditions. A systematic study of the correlation between the stereochemical outcome of the reaction and the substitution pattern at the two aldehydes is presented. The results can be used as guidelines to predict the product stereochemistry. This journal is

Ynamide Smiles Rearrangement Triggered by Visible-Light-Mediated Regioselective Ketyl-Ynamide Coupling: Rapid Access to Functionalized Indoles and Isoquinolines

In the past decades, significant advances have been made on radical Smiles rearrangement. However, the eventually formed radical intermediates in these reactions are limited to the amidyl radical, except for the few examples initiated by a N-centered radical. Here, a novel and practical radical Smiles rearrangement triggered by photoredox-catalyzed regioselective ketyl-ynamide coupling is reported, which represents the first radical Smiles rearrangement of ynamides. This method enables facile access to a variety of valuable 2-benzhydrylindoles with broad substrate scope in generally good yields under mild reaction conditions. In addition, this chemistry can also be extended to the divergent synthesis of versatile 3-benzhydrylisoquinolines through a similar ketyl-ynamide coupling and radical Smiles rearrangement, followed by dehydrogenative oxidation. Moreover, such an ynamide Smiles rearrangement initiated by intermolecular photoredox catalysis via addition of external radical sources is also achieved. By control experiments, the reaction was shown to proceed via key ketyl radical and α-imino carbon radical intermediates.