134029-62-2

Basic information

• Product Name: DMU-212
• 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

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: DMU-212(CAS DataBase Reference)
• NIST Chemistry Reference: DMU-212(134029-62-2)
• EPA Substance Registry System: DMU-212(134029-62-2)

Safety Data

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

Upstream product

• 61240-20-8 triphenyl-(3,4,5-trimethoxybenzyl)phosphonium bromide 
• 123-11-5 4-methoxy-benzaldehyde 
• 159386-48-8 (3,4,5-trimethoxybenzyl)diphenylphosphine oxide 
• 205366-79-6 2-(4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethan-1-ol 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 134029-74-6 [(3,4,5-trimethoxyphenyl)methyl]phosphoric acid diethyl ester 
• 637-69-4 4-Methoxystyrene 
• 2675-79-8 1-bromo-3,4,5-trimethoxybenzene 
• 1145-93-3 diethyl 4-methoxybenzylphosphonate 
• 1530-38-7 ((4-methoxyphenyl)methyl)triphenylphosphonium bromide 
• 943749-33-5 C₁₈H₂₂O₆S 
• 3588-30-5 2-methoxy-1,3-butadiene 
• 2091-46-5 triphenyl(prop-2-ynyl)phosphonium bromide 
• 2746-25-0 p-Methoxybenzyl bromide 

Downstream Products

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

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.

Nitrosoarene-Catalyzed HFIP-Assisted Transformation of Arylmethyl Halides to Aromatic Carbonyls under Aerobic Conditions

A rare metal-free nucleophilic nitrosoarene catalysis accompanied by highly hydrogen-bond-donor (HBD) solvent, 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP), organocatalytically converts arylmethyl halides to aromatic carbonyls. This protocol offers an effective means to access a diverse array of aromatic carbonyls with good chemoselectivity under mild reaction conditions. The activation of arylmethyl halides by HFIP to generate stable carbocation and autoxidation of in situ generated hydroxylamine to nitrosoarene in the presence of atmospheric O2 are the keys to success.

Tandem Acceptorless Dehydrogenative Coupling-Decyanation under Nickel Catalysis

The development of new catalytic processes based on abundantly available starting materials by cheap metals is always a fascinating task and marks an important transition in the chemical industry. Herein, a nickel-catalyzed acceptorless dehydrogenative coupling of alcohols with nitriles followed by decyanation of nitriles to access diversely substituted olefins is reported. This unprecedented C=C bond-forming methodology takes place in a tandem manner with the formation of formamide as a sole byproduct. The significant advantages of this strategy are the low-cost nickel catalyst, good functional group compatibility (ether, thioether, halo, cyano, ester, amino, N/O/S heterocycles; 43 examples), synthetic convenience, and high reaction selectivity and efficiency.

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.

Synthesis of Stilbenes by Rhodium-Catalyzed Aerobic Alkenylation of Arenes via C-H Activation

Arene alkenylation is commonly achieved by late transition metal-mediated C(sp2)-C(sp2) cross-coupling, but this strategy typically requires prefunctionalized substrates (e.g., with halides or pseudohalides) and/or the presence of a directing group on the arene. Transition metal-mediated arene C-H activation and alkenylation offers an alternative method to functionalize arene substrates. Herein, we report a rhodium-catalyzed oxidative arene alkenylation from arenes and styrenes to prepare stilbene and stilbene derivatives. The reaction is successful with several functional groups on both the arene and the olefin including fluoride, chloride, trifluoromethyl, ester, nitro, acetate, cyanide, and ether groups. Reactions of monosubstituted arenes are selective for alkenylation at the meta and para positions, generally with approximately 2:1 selectivity, respectively. Resveratrol and (E)-1,2,3-trimethoxy-5-(4-methoxystyryl)benzene (DMU-212) are synthesized by this single-step approach in high yield. Comparison with palladium catalysis showed that rhodium catalysis is more selective for meta-functionalization for monosubstituted arenes and that the Rh catalysis has better tolerance of halogen groups.

Water as a Hydrogenating Agent: Stereodivergent Pd-Catalyzed Semihydrogenation of Alkynes

Palladium-catalyzed transfer semihydrogenation of alkynes using H2O as the hydrogen source and Mn as the reducing reagent is developed, affording cis- and trans-alkenes selectively under mild conditions. In addition, this method provides an efficient way to access various cis-1,2-dideuterioalkenes and trans-1,2-dideuterioalkenes by using D2O instead of H2O.

Nickel(ii)-catalyzed direct olefination of benzyl alcohols with sulfones with the liberation of H2

A nickel(ii)-catalyzed direct olefination of benzyl alcohols with sulfones to access various terminal and internal olefins with the liberation of hydrogen gas is reported.

Highly E-Selective, Stereoconvergent Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Alkenyl Ethers

An improved method for the nickel-catalyzed Suzuki-Miyaura cross-coupling of alkenyl ethers is reported. This stereoconvergent protocol allows for the utilization of a wide range of alkenyl ethers and aryl boronic esters for the synthesis of variously sub

Novel Carbazole-Based N-Heterocyclic Carbene Ligands to Access Synthetically Relevant Stilbenes in Pd-Catalyzed Coupling Processes

A series of new carbazole-based N-heterocyclic carbene (NHC) ligands have been synthesized in a simple and facile synthetic route and subsequently used in a Pd/carbazole-based NHC catalytic system, which was found to be effective in catalyzing Heck reactions to provide substituted stilbene derivatives in good yields. Several bioactive stilbenes, including pterostilbene, pinosylvin, trimethoxy resveratrol, and resveratrol, were synthesized in good yields, and a 10 mmol scale-up was also performed for trimethoxy resveratrol. The synthetic application was also extended by performing a double-tandem chemoselective Heck reaction followed by Miyaura borylation in a one-pot procedure to give single-step access to synthetically useful stilbenyl boronate esters. Similarly, a unique triple-tandem protocol of a chemoselective Heck reaction/Miyaura borylation/Suzuki–Miyaura coupling reaction sequence was performed for the one-pot modification of biologically relevant molecules.