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 
• 74-88-4 methyl iodide 
• 2016-03-7 2,3-diphenylpropanal 
• 24379-49-5 (trimethylsilyl)phenyldiazomethane 
• 100-52-7 benzaldehyde 
• 151-50-8 potassium cyanide 
• 41997-47-1 1,1-diphenyl-2-propanol 
• 34317-82-3 2,3-diphenyl-crotonic acid 
• 10025-87-3 trichlorophosphate 
• 71-43-2 benzene 

Downstream Products

• 98-86-2 acetophenone 
• 65-85-0 benzoic acid 
• 833-81-8 (E)-1,2-diphenylpropene 
• 70671-91-9 3-bromo-1,2-diphenyl-propene 
• 67111-68-6 (R,R)-(+)-1-methyl-1,2-diphenylethane-1,2-diol 
• 100-52-7 benzaldehyde 
• 19643-70-0 (2R)-propane-1,2-diyldibenzene 
• 19643-68-6 (2S)-propane-1,2-diyldibenzene 
• 133815-74-4 1-methyl-2-morpholino-1,2-diphenylethanol 
• 133815-73-3 2-methyl-2-morpholino-1,2-diphenylethanol 
• 184046-33-1 (R,R)-1-Methyl-1,2-diphenyloxirane 
• 157605-73-7 (2S,3S)-2-methyl-2,3-diphenyloxirane 
• 1144522-17-7 (1-fluoroprop-2-ene-1,2-diyl)dibenzene 
• 5814-85-7 (-)-1,2-diphenylpropane 

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

Regioselective Synthesis of α-Functional Stilbenes via Precise Control of Rapid cis- trans Isomerization in Flow

The rapid cis-trans isomerization of α-anionic stilbene was regioselectively controlled by using flow microreactors, and its reaction with various electrophiles was conducted. The reaction time was precisely controlled within milliseconds to seconds at -50 °C to selectively give the cis- or trans-isomer in high yields. This synthetic method in flow was well-applied to synthesize precursors of commercial drug compound, (E)- and (Z)-tamoxifen with high regioselectivity and productivity.

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.