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4,4'-Dimethoxystilbene is an organic compound with the chemical formula C16H16O2. It is a derivative of stilbene, featuring two methoxy groups (-OCH3) attached to the para positions (1,1') of the benzene rings. This molecule is known for its potential applications in the synthesis of various pharmaceuticals and materials due to its unique structure. It is a colorless to pale yellow solid and is insoluble in water but soluble in organic solvents. The compound is often used as a precursor in the production of other chemicals and has been studied for its potential biological activities, although it is not widely used in commercial applications. It is important to handle 4,4'-dimethoxystilbene with care due to its potential health and environmental impacts.

1588-49-4

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1588-49-4 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 1588-49-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,8 and 8 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1588-49:
(6*1)+(5*5)+(4*8)+(3*8)+(2*4)+(1*9)=104
104 % 10 = 4
So 1588-49-4 is a valid CAS Registry Number.

1588-49-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name (E/Z)-4,4'-Dimethylstilben

1.2 Other means of identification

Product number -
Other names 4,4'-dimethyl stilbene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1588-49-4 SDS

1588-49-4Relevant academic research and scientific papers

Intermolecular Reductive Cross Coupling of Carbonyl Compounds with Nitriles Induced by Low-valent Titanium

Gao, Ju,Hu, Ming-yang,Chen, Jian-xie,Yuan, Su,Chen, Wei-xing

, p. 1617 - 1620 (1993)

Intermolecular cross coupling of carbonyl compounds with nitriles promoted by TiCl4-Zn leads to ketones.

A new method for reductive coupling of carbonyl compounds to olefins

Kumar Dutta,Konwar

, p. 6227 - 6229 (2000)

Aromatic and aliphatic aldehydes and ketones react with AlCl3-Zn in acetonitrile to yield olefins in good yield. (C) 2000 Published by Elsevier Science Ltd.

Flash Vacuum Pyrolysis of Sulphonyl Stabilised Phosphorus Ylides: Generation and Reactivity of Sulphonyl Carbenes

Aitken, R. Alan,Drysdale, Martin J.

, p. 512 - 513 (1991)

Thermal decomposition of arylmethylsulphonylalkylidenetriphenylphosphoranes results in loss of Ph3P and SO2 to give alkenes and in some cases products derived from benzylic radicals, the products are explained by a mechanism involving sulphonyl carbenes.

Synthesis, crystal structure, and catalytic activity of bridged-bis(N-heterocyclic carbene) palladium(II) complexes in selective Mizoroki-Heck cross-coupling reactions

El Ali, Bassam,Fettouhi, Mohammed,Iali, Wissam,Mansour, Waseem,Suleiman, Rami

, (2021/08/09)

A series of three 1,3-propanediyl bridged bis(N-heterocyclic carbene)palladium(II) complexes (Pd-BNH1, Pd-BNH2, and Pd-BNH3), with + I effect order of the N-substituents of the ligand (isopropyl > benzyl > methoxyphenyl), was the subject of a spectroscopic, structural, computational and catalytic investigation. The bis(NHC)PdBr2 complexes were evaluated in Mizoroki-Heck coupling reactions of aryl bromides with styrene or acrylate derivatives and showed high catalytic efficiency to produce diarylethenes and cinnamic acid derivatives. The X-ray structure of the most active palladium complex Pd-BNH3 shows that the Pd(II) center is bonded to the two carbon atoms of the bis(N-heterocyclic carbene) and two bromide ligands in cis position, resulting in a distorted square planar geometry. The NMR data of Pd-BNH3 are consistent with a single chair-boat rigid conformer in solution with no dynamic behavior of the 8-membered ring palladacycle in the temperature range 25–120 °C. The catalytic activities of three Pd-bridged bis(NHC) complexes in the Mizoroki-Heck cross-coupling reactions were not found to have a direct correlation with +I effect order of the N-substituents of the ligand. However, a direct correlation was found between the DFT calculated absolute softness of the three complexes with their respective catalytic activity. The highest calculated softness, in the case of Pd-BNH3, is expected to favor the coordination steps of both the soft aryl bromides and alkenes in the Heck catalytic cycle.

Palladium nanoparticlesin situsynthesized onCyclea barbatapectin as a heterogeneous catalyst for Heck coupling in water, the reduction of nitrophenols and alkynes

Le, Van-Dung,Le, T. Cam-Huong,Chau, Van-Trung,Le, T. Ngoc-Duyen,Dang, Chi-Hien,Vo, T. To-Nguyen,Nguyen, Trinh Duy,Nguyen, Thanh-Danh

, p. 4746 - 4755 (2021/03/22)

This study develops an effective method for thein situsynthesis of palladium nanoparticles (PdNPs) usingCyclea barbatapectin as a green reducing and stabilizing reagent. The PdNP@pectin nanocomposite was well characterized by analysis techniques such as UV-vis, FTIR, EDX, XRD, SEM, HR-TEM and STEM-mapping. Crystalline PdNPs were found to be distributed in the size range of 1-25 nm with the highest frequency of 6-12 nm. PdNP@pectin exhibited excellent recyclable catalysis activity for the Heck coupling reaction in water medium. The kinetics and recyclability of nanoparticles were investigated for the catalytic reduction ofo-,m- andp-nitrophenol. The result showed a good catalysis efficiency with five successful recycles without compromising much. In particular, the nanocomposite was used as a catalyst for the conversion of alkynes intocis-alkenes with KOH/DMF as a hydrogenation source. The reaction was also utilized effectively for the synthesis of sex pheromones, includingPlutella xylostella((Z)-11-hexadecen-1-yl acetate) andCylas formicarius((Z)-3-dodecen-1-yl(E)-2-butenoate) with the total yields of 70% and 68%, respectively. Therefore, PdNPs supported onC. barbatapectin are promising catalysis materials for application in various fields.

Porous organic polymer supported rhodium as a heterogeneous catalyst for hydroformylation of alkynes to α,β-unsaturated aldehydes

Liang, Zuyu,Chen, Jianbin,Chen, Xin,Zhang, Kai,Lv, Jinhe,Zhao, Haowen,Zhang, Guoying,Xie, Congxia,Zong, Lingbo,Jia, Xiaofei

supporting information, p. 13721 - 13724 (2019/11/19)

A new porous organic polymer supported rhodium catalyst (Rh/POL-BINAPa&PPh3) has been developed for the hydroformylation of various alkynes to afford the corresponding α,β-unsaturated aldehydes with high chem- and stereoselectivity, excellent catalytic activity and good reusability (10 cycles). The heterogeneous catalyst exhibited more catalytic activity than the comparable homogeneous Rh/BINAPa/PPh3 system.

Synthesis and Catalytic Applications of [N,N]-Pyrrole Ligands for the Regioselective Synthesis of Styrene Derivatives

Hochberger-Roa, Frank,Cortés-Mendoza, Salvador,Gallardo-Rosas, David,Toscano, Ruben A.,Ortega-Alfaro, M. Carmen,López-Cortés, José G.

, p. 4055 - 4064 (2019/07/31)

We report the synthesis of two [N,N]-donor ligands (5 a–b) containing a 2-chalcogenazoline as the structural motif. These compounds were synthesized from a common intermediate Fischer type aminocarbene complex (3). The palladium-complexes of these [N,N]-donor ligands were successfully used as catalytic precursors in the Mizoroki-Heck coupling reaction between aryl halides and methyl acrylate, styrene and ethylene. For methyl acrylates, high yields with TOF values between 0.6 and 5.5×105 h?1 were obtained. In the case of ethylene, we reached high regioselectivities to obtain a diversity of styrene derivatives under soft pressure conditions, with good values of TON and TOF. (Figure presented.).

Synthesis of [7]Helicene Enantiomers and Exploratory Study of Their Conversion into Helically Chiral Iodoarenes and Iodanes

Antien, Kevin,Pouységu, Laurent,Deffieux, Denis,Massip, Stéphane,Peixoto, Philippe A.,Quideau, Stéphane

supporting information, p. 2852 - 2858 (2019/02/05)

The facile and convenient preparation of both enantiomers of a [7]helicene scaffold from inexpensive (l)-(+)-tartaric acid and 4-methylstyrene is described. These helical structures were transformed into bis-iodinated ether derivatives in order to explore their potential as precursors of novel chiral organoiodane reagents or as iodoarene pre-catalysts. Promising results were obtained in hydroxylative phenol dearomatization/[4+2] cycloaddition cascade and dearomative spirolactonization reactions with encouraging enantiomeric excesses.

Immobilized Pd on (S)-methyl histidinate-modified multi-walled carbon nanotubes: A powerful and recyclable catalyst for Mizoroki-Heck and Suzuki-Miyaura C-C cross-coupling reactions in green solvents and under mild conditions

Hajipour, Abdol R.,Khorsandi, Zahra

, p. 256 - 261 (2016/05/02)

A stable and powerful heterogeneous palladium catalyst was synthesized using immobilized palladium on (S)-methyl histidinate bonded onto the surface of multi-walled carbon nanotubes. The catalyst was characterized using a combination of Fourier transform infrared and X-ray photoelectron spectroscopies, transmission electron microscopy, X-ray powder diffraction and inductively coupled plasma, thermogravimetric and elemental analyses. This new air- and moisture-stable phosphine-free palladium catalyst was found to be highly active and reusable in Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions in poly(ethylene glycol) and aqueous ethanol as green solvents using an extremely small amount of palladium under mild conditions.

Metal-catalyzed formal amidation of alkenes under CO-free condition

Zhang, Yuanyuan,Ye, Wenjing,Leng, Xue,He, Ying,Zhang, Hui,Xiao, Xiao

supporting information, p. 4203 - 4206 (2016/08/24)

An effective procedure for synthesis of amides from alkenes and [Formula presented] via Pd and Fe catalysts under mild conditions is described. A series of benzamides containing various functional groups can be obtained in reasonable yield and the possible reaction pathway is proposed in this Letter.

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