4705-34-4

Basic information

• Product Name: 4,4'-DIMETHOXYSTILBENE
• Synonyms: 4,4'-DIMETHOXYSTILBENE;4,4'-DIMETHOXY-TRANS-STILBENE;p,p'-dimethoxystilbene;4,4''-DIMETHOXYSTILBENE 99%;4,4'-Dimethoxystilbene,99%
• CAS NO: 4705-34-4
• Molecular Formula: C₁₆H₁₆O₂
• Molecular Weight: 240.3
• EINECS: 225-189-9
• Mol File: 4705-34-4.mol
• Article Data: 209

Chemical Properties

• Melting Point: 213-215 °C
• Boiling Point: 323.02°C (rough estimate)
• Appearance: White/Glistening Flakes
• Density: 1.1228 (rough estimate)
• Refractive Index: 1.4700 (estimate)
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility: Chloroform (Slightly, Sonicated), Ethyl Acetate (Slightly, Sonicated)
• Stability: Light Sensitive
• CAS DataBase Reference: 4,4'-DIMETHOXYSTILBENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-DIMETHOXYSTILBENE(4705-34-4)
• EPA Substance Registry System: 4,4'-DIMETHOXYSTILBENE(4705-34-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 37/39-26
• Hazardous Substances Data: 4705-34-4(Hazardous Substances Data)

Usage

Description

4,4'-DIMETHOXYSTILBENE is an organic compound that serves as an intermediate in the synthesis of nonsteroidal, selective estrogen receptor modulator (SERM), Raloxifene (R100000). It is characterized by its white glistening flake appearance.

Uses

Used in Pharmaceutical Industry:
4,4'-DIMETHOXYSTILBENE is used as an intermediate in the synthesis of Raloxifene, a nonsteroidal selective estrogen receptor modulator (SERM). It plays a crucial role in the development of this medication, which is utilized for the treatment and prevention of osteoporosis in postmenopausal women and also for the reduction of the risk of invasive breast cancer in patients with osteoporosis.
Additionally, Raloxifene has been studied for its potential use in treating other conditions, such as prostate cancer and certain cardiovascular diseases, further expanding the importance of 4,4'-DIMETHOXYSTILBENE in the pharmaceutical industry.

Synthesis Reference(s)

The Journal of Organic Chemistry, 26, p. 4158, 1961 DOI: 10.1021/jo01068a638Synthetic Communications, 21, p. 841, 1991 DOI: 10.1080/00397919108019767Tetrahedron, 43, p. 2741, 1987 DOI: 10.1016/S0040-4020(01)86879-4

Upstream product

• 2299-73-2 N,N-bis(4-methoxybenzylidene)hydrazine 
• 120-44-5 1,4-di(4-methoxyphenyl)ethanone 
• 693-04-9 butyl magnesium bromide 
• 10557-57-0 propylmagnesium iodide 
• 60-29-7 diethyl ether 
• 72-43-5 Methoxychlor 
• 925-90-6 ethylmagnesium bromide 
• 72030-65-0 1,2-dibenzoyl-3,4-bis-(4-methoxy-phenyl)-cyclobutane 
• 20498-71-9 1,2-bis(4-methoxyphenyl)ethan-1-ol 
• 31263-13-5 Bis-(4-methoxy-phenyl)-fumarat 
• 55539-39-4 p-methoxybenzylphenylsulfone 
• 637-69-4 4-Methoxystyrene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 78-08-0 Triethoxyvinylsilane 

Downstream Products

• 90285-21-5 C₁₆H₁₆O₂^(1-) 
• 4464-76-0 1,2-bis(4-methoxyphenyl)ethane-1,2-diol 
• 67307-24-8 Acetic acid 6-methoxy-2,3,4-tris-(4-methoxy-phenyl)-1,2,3,4-tetrahydro-naphthalen-1-yl ester 
• 39090-32-9 Acetic acid (1R,2S)-2-acetoxy-1,2-bis-(4-methoxy-phenyl)-ethyl ester 
• 120-44-5 1,4-di(4-methoxyphenyl)ethanone 
• 39090-33-0 2,3-bis(p-methoxyphenyl)oxirane 
• 123-11-5 4-methoxy-benzaldehyde 
• 2510-75-0 trans-4,4'-dimethoxystilbene radical cation 
• 1657-55-2 1,2-bis(4-methoxyphenyl)ethane 
• 61732-72-7 meso-1,2-dibromo-1,2-di(4-methoxyphenyl)-2-ethane 
• 122798-27-0 (-)-(2S,3S)-1,2-bis(4-methoxyphenyl)ethane1,2-diol 
• 448293-94-5 (3S,5S,6S)-3-[(S)-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl-methyl]-5,6-bis-(4-methoxy-phenyl)-[1,4]dioxan-2-one 
• 448294-00-6 (2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-cyclohexyl-2-[(1S,2S)-2-hydroxy-1,2-bis-(4-methoxy-phenyl)-ethoxy]-propionic acid methyl ester 

Relevant articles and documents

Olefin Metathesis, p-Cresol, and the Second Generation Grubbs Catalyst: Fitting the Pieces

p-Cresol as additive to the Grubbs second generation catalyst (GII) allows the cross-metathesis of acrylates with prop-1-en-1-ylbenzenes under conditions that only give the prop-1-en-1-ylbenzene self-metathesis product in the absence of cresol. NMR and IR spectroscopy, MALDI-TOF MS and XPS supported the formation of a ruthenium benzylidene with hydrogen bonds between p-cresol and the chloride ligands of GII. XPS furthermore confirmed p-cresol to increase the binding energies of the GII Ru 3d5/2, 3d3/2, 3p3/2 and 3p1/2 photoelectron lines, whereas 1H NMR spectroscopy indicated the carbene carbon and hydrogen to be shielded. It is thus postulated that p-cresol allows for more facile interaction between electron-deficient compounds and the ruthenium benzylidene by decreasing the electron density on the metal center and increasing the electron density on the carbene.

Synthesis of ethylene bis [(2-hydroxy-5,1,3-phenylene) bis methylene] tetraphosphonic acid and their anticorrosive effect on carbon steel in 3%NaCl solution

The inhibition performance of the newly synthesized Ethylene bis [(2-hydroxy-5,1,3-phenylene) bis methylene] tetraphosphonic acid (ETPA) toward carbon steel in 3% NaCl was investigated at different concentrations using potentiodynamic polarization (PDP) and impedance spectroscopy (EIS) methods. It was found that the inhibition capability was increased with increasing inhibitor dose and reach 92% at 10?3 mol/L. Also, Polarization curves showed that ETPA acts as a mixed type inhibitor with predominantly control of anodic reaction. The new inhibitor was investigated by different spectroscopic methods such as 1H, 13C and 31PNMR. The quantum parameters such as absolute electronegativity (χ), energy gap ΔE (EHOMO-ELUMO), global softness (σ), global hardness (η), electrophilicity index (ω) and the number of transfer electrons (ΔN) are calculated by density functional theory (DFT). The experimental also correlated with density functional theory results. The calculations show that ETPA has high density of negative charge located on the oxygen atoms of the phosphonate group facilitating the adsorption of ETPA on the surface of carbon steel. The inhibition efficiency of ETPA was discussed in terms of blocking of electrode surface by adsorption of ETPA molecules through active centers. The adsorption of ETPA on the surface of carbon steel obeyed the Langmuir isotherm paradigm.

A photocatalyst-free visible-light-mediated solvent-switchable route to stilbenes/vinyl sulfones from β-nitrostyrenes and arylazo sulfones

Photocatalyst-free visible-light-mediated reactions, based on the presence of a visible-light-absorbing functional group in the starting material itself in order to exclude the often costly, hazardous, degradable and difficult to remove or recover photoredox catalysts, have been gaining momentum recently. We have employed this approach to develop a denitrative photocatalyst-free visible-light-mediated protocol for the arylation/sulfonylation of β-nitrostyrenes employing arylazo sulfones (bench-stable photolabile compounds) in a switchable solvent-controlled manner. Arylazo sulfones served as the aryl and sulfonyl radical precursors under blue LED irradiation for the synthesis oftrans-stilbenes and (E)-vinyl sulfones in CH3CN and dioxane/H2O 2?:?1, respectively. The absence of any metal, photocatalyst and additive; excellent selectivity (E-stereochemistry) and solvent-switchability; and the use of visible light and ambient temperature are the prime assets of the developed method. Moreover, we report the first photocatalyst-free visible light-driven route to synthesize stilbenes and vinyl sulfones from readily available β-nitrostyrenes.