4714-24-3

Basic information

• Product Name: 4-Bromostilbene
• Synonyms: 4-BROMOSTILBENE;4-Bromostilbeneep;1-Bromo-4-(2-phenylethenyl)- Benzene;1-Bromo-4-(2-phenylvinyl)benzene;4-Bromo-trans-stilbene;4-broMo-stilbene, 4-broMostilbene, 1-broMo-4-[2-phenylvinyl]benzene;1-Bromo-4-styrylbenzene;(E)-1-bromo-4-styrylbenzene
• CAS NO: 4714-24-3
• Molecular Formula: C₁₄H₁₁Br
• Molecular Weight: 259.14
• Product Categories: Stilbenes
• Mol File: 4714-24-3.mol
• Article Data: 98

Chemical Properties

• Melting Point: 140 °C
• Boiling Point: 342 °C at 760 mmHg
• Flash Point: 159.1 °C
• Appearance: /
• Density: 1.372 g/cm³
• Vapor Pressure: 0.000153mmHg at 25°C
• Refractive Index: 1.679
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-Bromostilbene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromostilbene(4714-24-3)
• EPA Substance Registry System: 4-Bromostilbene(4714-24-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-52
• WGK Germany: 3
• Hazardous Substances Data: 4714-24-3(Hazardous Substances Data)

Usage

General Description

4-Bromostilbene is an organic compound with the chemical formula C14H11Br. It is a derivative of the compound stilbene, which consists of two phenyl groups connected by a ethene bridge. 4-Bromostilbene is used as a starting material in the synthesis of various pharmaceuticals and agrochemicals. It is also used in research as a reagent and intermediate in organic synthesis. The compound has potential applications in the fields of medicine, agriculture, and material science due to its unique chemical properties. However, it is important to handle 4-Bromostilbene with caution due its toxic and irritant properties.

InChI:InChI=1/C14H11Br/c15-14-10-8-13(9-11-14)7-6-12-4-2-1-3-5-12/h1-11H/b7-6+

Upstream product

• 1100-88-5 benzyltriphenylphosphonium chloride 
• 1122-91-4 4-bromo-benzaldehyde 
• 51044-13-4 4-bromobenzyl triphenylphosphonium bromide 
• 100-52-7 benzaldehyde 
• 42497-88-1 4-(4-nitrophenylsulfonylmethyl)benzene 
• 92439-75-3 (E)-3-(4-bromophenyl)-2-phenylacrylic acid 
• 100-42-5 styrene 
• 108-86-1 bromobenzene 
• 38186-51-5 diethyl (4-bromobenzyl)phosphonate 
• 591-50-4 iodobenzene 
• 71-43-2 benzene 
• 5467-74-3 4-Bromophenylboronic acid 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 98-80-6 phenylboronic acid 

Downstream Products

• 1382353-92-5 (Z)-2-(4-styrylphenylamino)benzamide 
• 107328-76-7 (E)-1-(4-styrylphenyl)propan-1-one 
• 943858-44-4 C₆H₅CHCH(C₆H₄(Bpin)-4) 
• 14525-88-3 trans-1-(p-bromophenyl)-2-phenylcyclopropane 
• 13041-79-7 4-cyanostilbene 
• 21175-18-8 4-styrylbiphenyl 

Relevant articles and documents

METHODS OF ARENE ALKENYLATION

The present disclosure provides for a rhodium-catalyzed oxidative arene alkenylation from arenes and styrenes to prepare stilbene and stilbene derivatives. For example, the present disclosure provides for method of making arenes or substituted arenes, in particular stilbene and stilbene derivatives, from a reaction of an optionally substituted arene and/or optionally substituted styrene. The reaction includes a Rh catalyst or Rh pre-catalyst material and an oxidant, where the Rh catalyst or Rh catalyst formed Rh pre-catalyst material selectively functionalizes CH bond on the arene compound (e.g., benzene or substituted benzene).

Structural Effect of Pincer Pd(II)–ONO Complexes Modified with Acylthiourea on Sizes of the In Situ Generated Pd Nanoparticles During Heck Coupling Reaction

Abstract: The Pd nanoparticles generated in situ from Pd–pincer complexes catalyzed Heck coupling reaction. For this purpose, new Pd(II)–ONO pincer complexes (1–4) containing acylthiourea ancillary ligand were obtained by treating [Pd(ONO)(CH3CN)] with the respective N-substituted carbamothioyl benzamide ligand (L1–L4). Formation of these complexes was confirmed by UV–Visible, FT-IR, NMR and mass spectroscopic techniques. The sizes of in situ formed Pd nanoparticles were greatly affected by the substituent in ancillary ligand, which in turn influenced their catalytic activity towards Heck coupling reaction. The in situ formed Pd nanoparticles during Heck reaction were removed from the reaction medium and analyzed using HR-TEM to estimate the sizes of the Pd nanoparticles. Complex [Pd(ONO)((N-benzylcarbamothioyl)benzamide)] (1) which does not possess any substituent on the benzyl moiety of acylthiourea produced the smallest Pd nanoparticles with the average particle size of 3.7?nm. Hence, complex 1 showed the utmost catalytic activity. With complex 1, 51–99% of conversion was observed during Heck coupling reaction of styrene with various aryl halides. XPS results confirmed that the recovered black particles were Pd(0). A reasonable recyclability results were achieved by these in situ generated Pd nanoparticles. Graphic Abstract: [Figure not available: see fulltext.]

An Amine-Assisted Ionic Monohydride Mechanism Enables Selective Alkyne cis-Semihydrogenation with Ethanol: From Elementary Steps to Catalysis

The selective synthesis of Z-alkenes in alkyne semihydrogenation relies on the reactivity difference of the catalysts toward the starting materials and the products. Here we report Z-selective semihydrogenation of alkynes with ethanol via a coordination-induced ionic monohydride mechanism. The EtOH-coordination-driven Cl- dissociation in a pincer Ir(III) hydridochloride complex (NCP)IrHCl (1) forms a cationic monohydride, [(NCP)IrH(EtOH)]+Cl-, that reacts selectively with alkynes over the corresponding Z-alkenes, thereby overcoming competing thermodynamically dominant alkene Z-E isomerization and overreduction. The challenge for establishing a catalytic cycle, however, lies in the alcoholysis step; the reaction of the alkyne insertion product (NCP)IrCl(vinyl) with EtOH does occur, but very slowly. Surprisingly, the alcoholysis does not proceed via direct protonolysis of the Ir-C(vinyl) bond. Instead, mechanistic data are consistent with an anion-involved alcoholysis pathway involving ionization of (NCP)IrCl(vinyl) via EtOH-for-Cl substitution and reversible protonation of Cl- ion with an Ir(III)-bound EtOH, followed by β-H elimination of the ethoxy ligand and C(vinyl)-H reductive elimination. The use of an amine is key to the monohydride mechanism by promoting the alcoholysis. The 1-amine-EtOH catalytic system exhibits an unprecedented level of substrate scope, generality, and compatibility, as demonstrated by Z-selective reduction of all alkyne classes, including challenging enynes and complex polyfunctionalized molecules. Comparison with a cationic monohydride complex bearing a noncoordinating BArF- ion elucidates the beneficial role of the Cl- ion in controlling the stereoselectivity, and comparison between 1-amine-EtOH and 1-NaOtBu-EtOH underscores the fact that this base variable, albeit in catalytic amounts, leads to different mechanisms and consequently different stereoselectivity.