779-51-1

Basic information

• Product Name: ALPHA-METHYLSTILBENE
• Synonyms: [(1E)-2-Phenyl-1-propenyl]benzene;1,2-Diphenyl-1-propene;1,2-Diphenylpropene;1-Methyl-1,2-diphenylethene;1-Propene, 1,2-diphenyl-;1-propene,1,2-diphenyl-;Benzene, 1,1'-(1-methyl-1,2-ethenediyl)bis-;benzene,1,1’-(1-methyl-1,2-ethenediyl)bis-
• CAS NO: 779-51-1
• Molecular Formula: C₁₅H₁₄
• Molecular Weight: 194.27
• EINECS: 212-300-0
• Mol File: 779-51-1.mol
• Article Data: 99

Chemical Properties

• Melting Point: 81-83 °C(lit.)
• Boiling Point: 285-286 °C(lit.)
• Flash Point: 124.5 °C
• Appearance: /
• Density: 0,986 g/cm3
• Vapor Pressure: 0.00571mmHg at 25°C
• Refractive Index: 1.5635
• CAS DataBase Reference: ALPHA-METHYLSTILBENE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA-METHYLSTILBENE(779-51-1)
• EPA Substance Registry System: ALPHA-METHYLSTILBENE(779-51-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 779-51-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 40, p. 1662, 1975 DOI: 10.1021/jo00899a039Synthetic Communications, 13, p. 87, 1983 DOI: 10.1080/00397918308061963Tetrahedron Letters, 23, p. 1979, 1982 DOI: 10.1016/S0040-4039(00)87238-X

InChI:InChI=1/C15H14/c1-13(15-10-6-3-7-11-15)12-14-8-4-2-5-9-14/h2-12H,1H3/b13-12+

Upstream product

• 451-40-1 phenyl benzyl ketone 
• 917-64-6 methyl magnesium iodide 
• 5342-87-0 1,2-diphenylpropane-2-ol 
• 60-29-7 diethyl ether 
• 3360-53-0 1-bromo-2-phenyl-1-propene 
• 74421-26-4 2,2-diphenylpropan-1-ol 
• 108-24-7 acetic anhydride 
• 103-79-7 1-phenyl-acetone 
• 74-88-4 methyl iodide 
• 2016-03-7 2,3-diphenylpropanal 
• 948-97-0 2,3-diphenyl-1-propene 
• 33973-48-7 diethyl (1-phenylethyl)phosphonate 
• 100-52-7 benzaldehyde 
• 77815-44-2 1-phenyl-1-phenylthio-1-trimethylsilylethane 

Downstream Products

• 98-86-2 acetophenone 
• 65-85-0 benzoic acid 
• 5809-65-4 3,4-diphenyl-but-3-enoic acid 
• 10282-18-5 α-methylstilbene oxide 
• 5814-85-7 1,2-diphenylpropane 
• 875852-83-8 1,2-dibromo-1,2-diphenyl-propane 
• 858010-45-4 1-bromo-2,3-diphenyl-propane 
• 833-81-8 (E)-1,2-diphenylpropene 
• 51507-26-7 acetic acid-((1RS,2SR)-1-methyl-2-nitro-1,2-diphenyl-ethyl ester) 
• 14161-76-3 1,1-Dichlor-3-methyl-2,3-diphenyl-cyclopropan 
• 70671-91-9 3-bromo-1,2-diphenyl-propene 
• 7693-84-7 (1RS,2SR)-1,2-diphenyl-propan-1-ol 
• 883-20-5 9-methylphenanthrene 
• 63904-72-3 (E)-(1-bromoprop-1-ene-1,2-diyl)dibenzene 

Relevant articles and documents

Pd-Catalyzed Coupling of N-Tosylhydrazones with Benzylic Phosphates: Toward the Synthesis of Di- or Tri-Substituted Alkenes

This study shows that various di- and tri-substituted alkenes with high chemoselectivity were obtained in good to high yields by coupling N-tosylhydrazones (NTHs) with benzylic phosphates as electrophilic partners. The obtained new catalytic system consis

Synthesis of new adamantyl-imine palladium(II) complexes and their application in Mizoroki-Heck and Suzuki-Miyaura C[sbnd]C cross-coupling reactions

Improving carbon–carbon cross-coupling reactions is an ongoing process and finding the most versatile and stable catalyst precursors has been of great interest. Ligand design has been proven to be important since it is responsible for providing electron density and steric saturation around the metal centre, thus contributing towards the stereo-electronic properties. The adamantyl moiety has been used to generate highly bulky and electron-rich ligands for application in palladium-catalysed cross-coupling reactions. Accordingly, we have prepared some Schiff-base adamantyl ligands (L1-L3) and complexed them with [PdCl2(MeCN)2] to afford the (pre)catalysts C1-C3, which were successfully applied in Mizoroki-Heck and Suzuki-Miyaura carbon–carbon cross-coupling reactions. The cross-coupling reaction products were obtained in good yields using 0.5 mol % Pd catalyst loading. C2 and C3 showed remarkable activity in the Mizoroki-Heck coupling reactions involving substrates with substituents on the olefin and aryl halide (including 4-Cl, 4-CH3, -CO2Me and -CO2Et). We also, observed that the Suzuki-Miyaura cross-coupling system was active towards challenging activated and deactivated aryl chlorides, with to up 70% conversions recorded. The mercury poisoning tests conducted revealed that the catalysts act as homogenous molecular active species in the Mizoroki-Heck reactions and act as both homogenous and heterogeneous catalysts in the Suzuki-Miyaura cross-coupling reactions.

Highly Stereoselective Positional Isomerization of Styrenes via Acid-Catalyzed Carbocation Mechanism

The first transition metal-free highly stereoselective positional isomerization of various α-alkyl styrenes through a carbocation mechanism triggered strategy is developed by using Al(OTf)3 as a hidden Br?nsted acid catalyst, which provides facile access to value-added acyclic tri- and tetra-substituted alkenes in good yields with high stereoselectivity under mild conditions. The practicality of this protocol is further highlighted by the gram-scale synthesis, high stereoselectivity, good functional group tolerance, and simple operation. Mechanistic studies support that Al(OTf)3 acts as a hidden Br?nsted acid catalyst and a carbocation intermediate is formed.