134029-62-2

Basic information

• Product Name: 3,4,5,4'-TETRAMETHOXYSTILBENE
• Synonyms: 3,4,5,4'-TETRAMETHOXYSTILBENE;(E)-1,2,3-Trimethoxy-5-[2-(4-methoxyphenyl)ethenyl]benzene;DMU 212;(E)-3,4,5,4′-Tetramethoxystilbene;1,2,3-Trimethoxy-5-[(1E)-2-(4-methoxyphenyl)ethenyl]-benzene
• CAS NO: 134029-62-2
• Molecular Formula: C₁₈H₂₀O₄
• Molecular Weight: 300.349
• EINECS: 1312995-182-4
• Mol File: 134029-62-2.mol
• Article Data: 50

Chemical Properties

• Melting Point: 157-159℃
• Boiling Point: 444.027 °C at 760 mmHg
• Flash Point: 144.057 °C
• Appearance: white to beige/
• Density: 1.117
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble5mg/mL, clear (warmed)
• CAS DataBase Reference: 3,4,5,4'-TETRAMETHOXYSTILBENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5,4'-TETRAMETHOXYSTILBENE(134029-62-2)
• EPA Substance Registry System: 3,4,5,4'-TETRAMETHOXYSTILBENE(134029-62-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 134029-62-2(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder

Upstream product

• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 2746-25-0 p-Methoxybenzyl bromide 
• 943749-33-5 C₁₈H₂₂O₆S 
• 1530-38-7 ((4-methoxyphenyl)methyl)triphenylphosphonium bromide 
• 1145-93-3 diethyl 4-methoxybenzylphosphonate 
• 123-11-5 4-methoxy-benzaldehyde 
• 134029-74-6 [(3,4,5-trimethoxyphenyl)methyl]phosphoric acid diethyl ester 
• 205366-79-6 2-(4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethan-1-ol 
• 159386-48-8 (3,4,5-trimethoxybenzyl)diphenylphosphine oxide 
• 61240-20-8 triphenyl-(3,4,5-trimethoxybenzyl)phosphonium bromide 
• 13338-63-1 2-(3,4,5-trimethoxyphenyl)acetonitrile 
• 105-13-5 4-Methoxybenzyl alcohol 
• 637-69-4 4-Methoxystyrene 
• 182163-96-8 3,4,5-trimethoxyphenylboronic Acid 

Downstream Products

• 22255-22-7 3,5,4'-trimethoxy-trans-stilbene 
• 83638-45-3 1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethane 
• 78916-50-4 1,3-dimethoxy-5-(2-phenylethyl)benzene 
• 35450-81-8 1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethane 
• 205366-80-9 (1R,2R)-1-(4-Methoxy-phenyl)-2-(3,4,5-trimethoxy-phenyl)-ethane-1,2-diol 
• 205366-87-6 (1S,2S)-1-(4-Methoxy-phenyl)-2-(3,4,5-trimethoxy-phenyl)-ethane-1,2-diol 

Relevant articles and documents

Oxazoline chemistry. Part 12: A metal-mediated synthesis of DMU-212; X-ray diffraction studies of an important anti-cancer agent

An improved synthesis of the anti-cancer agent DMU-212 (trans-3,4,5, 4′-tetramethoxystilbene) is described. The methodology involves the use of a Pd-oxazoline catalyst as a mediator of a regio-selective (Heck) C-C bond formation reaction. A simple isolation step is then used to obtain the title material. The compound has been further characterised in the solid-state by X-ray diffraction methods.

Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (E)-Stilbenes and (1 E,3 E)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products

A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes to give (E)-olefins was disclosed. By the use of an organostibine reagent, this method can produce unsymmetric (E)-1,2-diarylethylenes and (1E,3E)-1,4-diarylbuta-1,3-dienes in good yields with high E/Z selectivity and good functional group tolerance. Resveratrol and DMU-212 were synthesized in high yield. The protocol can be extended to the synthesis of (1E,3E,5E)-1,6-diphenylhexa-1,3,5-triene in 40% yield. Products 5e, 5f, and 7a showed good photoluminescence quantum yields ranging from 72 to 99%.

Photocatalytic Isomerization of Styrenyl Halides: Stereodivergent Synthesis of Functionalized Alkenes

An efficient and general method for the isomerization of styrenyl halides under different photocatalytic conditions (fac-Ir(ppy)3 in methanol for E to Z isomerization and fluorescein in 1,4-dioxane for Z to E isomerization, respectively) is disclosed. A series of stereospecific transformations constitute preliminary validation of this strategy in the synthesis of functionalized alkenes, including two diaryl alkenes, a styrenyl boronic ester and an enyne. The photocatalytic isomerization and subsequent cross coupling reaction can be run in a one-pot manner. The stereodivergent synthesis of all four isomers of a conjugated diene, as well as the antitumor agent DMU-212 and its (Z)-isomer highlights the synthetic applicability of this method.