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2-Bromo-1-(3,4,5-trimethoxy-phenyl)-ethanone is a chemical compound with the molecular formula C11H13BrO4. It is a derivative of acetophenone, featuring a bromine atom and three methoxy groups attached to a phenyl ring. This versatile compound is known for its potential applications in the pharmaceutical and chemical industries due to its unique chemical structure.

51490-01-8

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51490-01-8 Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-1-(3,4,5-trimethoxy-phenyl)-ethanone is used as an intermediate in the synthesis of pharmaceuticals for its potential pharmacological properties. It plays a crucial role in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Organic Chemistry:
In the field of organic chemistry, 2-Bromo-1-(3,4,5-trimethoxy-phenyl)-ethanone is utilized as a reagent in various reactions. Its unique chemical structure allows for its use in a wide range of organic transformations, facilitating the synthesis of complex organic compounds.
Used in Anti-Inflammatory Research:
2-Bromo-1-(3,4,5-trimethoxy-phenyl)-ethanone has been studied for its potential anti-inflammatory properties. As a compound with such characteristics, it may contribute to the development of new treatments for inflammatory conditions, offering a promising avenue for further research and application in the medical field.

Check Digit Verification of cas no

The CAS Registry Mumber 51490-01-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,1,4,9 and 0 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 51490-01:
(7*5)+(6*1)+(5*4)+(4*9)+(3*0)+(2*0)+(1*1)=98
98 % 10 = 8
So 51490-01-8 is a valid CAS Registry Number.
InChI:InChI=1/C11H13BrO4/c1-14-9-4-7(8(13)6-12)5-10(15-2)11(9)16-3/h4-5H,6H2,1-3H3

51490-01-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-bromo-1-(3,4,5-trimethoxyphenyl)ethanone

1.2 Other means of identification

Product number -
Other names 2-bromo-3',4',5'-trimethoxyacetophenone

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:51490-01-8 SDS

51490-01-8Relevant articles and documents

New thiazole-2(3H)-thiones containing 4-(3,4,5-trimethoxyphenyl) moiety as anticancer agents

Ansari, Mahsa,Shokrzadeh, Mohammad,Karima, Saeed,Rajaei, Shima,Fallah, Marjan,Ghassemi-Barghi, Nasrin,Ghasemian, Majid,Emami, Saeed

, (2020)

A new series of thiazole-2(3H)-thiones containing 4-(3,4,5-trimethoxyphenyl) moiety were synthesized as diaryl-heterocylic analogs of combretastatin A-4 with anticancer activity. The cytotoxicity evaluation of synthesized compounds against cancer cell lin

Identification of novel non-toxic and anti-angiogenic α-fluorinated chalcones as potent colchicine binding site inhibitors

Sun, Moran,Yuan, Minghua,Kang, Yingying,Qin, Jinling,Zhang, Yixin,Duan, Yongtao,Wang, Longfei,Yao, Yongfang

, p. 339 - 354 (2022/01/10)

α-Fluorinated chalcones were prepared and evaluated for their cell growth inhibitory properties against six human cancer cell lines. The most potent chalcone 4c demonstrated excellent selective toxicity against cancer cells versus normal human cells, with

Antiproliferative Activity of Diarylnaphthofurans through Microtubule Destabilization

Bhukya, Balakishan,Chanda, Debabrata,Kaushal, Tanu,Khan, Feroz,Khan, Sana,Konwar, Rituraj,Kumar, Deepak,Kumar, Shailesh,Luqman, Suaib,Meena, Abha,Negi, Arvind S.,Parveen, Shahnaz,Singh, Diksha

, p. 443 - 455 (2021/11/22)

The present communication deals with pharmacophore designing based on “Fragment-Based Drug Discovery” approach. Two series of compounds were synthesized and evaluated against human cancer cell lines by sulforhodamine assay, target studies through tubulin

Alkylation of monomeric, dimeric, and polymeric lignin models through carbon-hydrogen activation using Ru-catalyzed Murai reaction

Zuleta, Ernesto C.,Bozell, Joseph J.

, (2021/10/05)

In this study, we have assessed directed carbon-hydrogen activation (CHA) for alkylation of monomeric, dimeric, and polymeric lignin models using Murai's catalyst [RuH2(CO)(PPh3)3]. Based on related work from our laboratory showing that isolated organosolv lignin bears benzylic directing groups ideal for CHA reactions, this approach could offer new methodology for the valorization of biorefinery lignin. Monomeric and dimeric models bearing a keto group at the benzylic position undergo Ru-catalyzed alkylation in good to excellent yield. Similarly, models bearing a benzylic OH group also undergo alkylation via a tandem oxidation/alkylation process enabled by the Ru catalyst. Polymeric models show low levels of functionalization as a result of the poor solubility of the starting polymer. With unsymmetrical models, functionalization occurs first at the least sterically hindered ortho-site, but a subsequent alkylation, leading to disubstituted products can occur at the more sterically hindered site, leading to hexasubstituted arenes. The reaction shows sensitivity to free phenolic OH groups, which appears to reduce the yield in some reactions, and is also a contributing factor to the low yields observed with polymeric lignin models. Combining CHA methodology with lignin isolation technology able to introduce appropriate directing groups for catalytic functionalization will form the basis for improved conversion of lignin to high value chemical products.

1,3,4-thiadiazine compound and application thereof

-

Paragraph 0023-0025; 0031; 0039-0040, (2020/08/06)

The invention relates to a 1,3,4-thiadiazine compound, and the chemical structure of the compound is shown as a formula (I). The provided compound has a remarkable inhibition effect on human cervicalcancer cells Hela and human colon cancer cells HCT116, a

In(OTf)3-catalyzed intramolecular hydroarylation of α-phenylallyl β-ketosulfones - synthesis of sulfonyl 1-benzosuberones and 1-tetralones

Chang, Meng-Yang,Chang, Yu-Lun,Lai, Kai-Xiang

, p. 18231 - 18244 (2020/06/08)

In(OTf)3-catalyzed intramolecular hydroarylation of α-phenylallyl β-ketosulfones provides sulfonyl 1-benzosuberones and 1-tetralones in moderate to good yields in refluxing (CH2Cl)2under open-vessel and easy-operation reaction conditions. A plausible mechanism is proposed and discussed. This highly regioselective protocol provides an atom-economic ring-closure route.

Development of triazolothiadiazine derivatives as highly potent tubulin polymerization inhibitors: Structure-activity relationship, in vitro and in vivo study

Ma, Weifeng,Chen, Peng,Huo, Xiansen,Ma, Yufeng,Li, Yanhong,Diao, Pengcheng,Yang, Fang,Zheng, Shengquan,Hu, Mengjin,You, Wenwei,Zhao, Peiliang

, (2020/10/08)

Based on our prior work, we reported the design, synthesis, and biological evaluation of fifty-two new triazolothiadiazine-based analogues of CA-4 and their preliminary structure-activity relationship. Among synthesized compounds, Iab was found to be the most potent derivative possessing IC50 values ranging from single-to double-digit nanomolar in vitro, and also exhibited excellent selectivity over the normal human embryonic kidney HEK-293 cells (IC50 > 100 μM). Further mechanistic studies revealed that Iab significantly blocked tubulin polymerization and disrupted the intracellular microtubule network of A549 cells. Moreover, Iab induced G2/M cell cycle arrest by regulation of p-cdc2 and cyclin B1 expressions, and caused cell apoptosis through up-regulating cleaved PARP and cleaved caspase-3 expressions, and down-regulating of Bcl-2. Importantly, in vivo, Iab effectively suppressed tumor growth of A549 lung cancers in a xenograft mouse model without obvious signs of toxicity, confirming its potential as a promising candidate for cancer treatment.

Highly Selective Oxidation and Depolymerization of α,γ-Diol-Protected Lignin

Lan, Wu,de Bueren, Jean Behaghel,Luterbacher, Jeremy S.

, p. 2649 - 2654 (2019/02/01)

Lignin oxidation offers a potential sustainable pathway to oxygenated aromatic molecules. However, current methods that use real lignin tend to have low selectivity and a yield that is limited by lignin degradation during its extraction. We developed stoichiometric and catalytic oxidation methods using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant/catalyst to selectively deprotect the acetal and oxidize the α-OH into a ketone. The oxidized lignin was then depolymerized using a formic acid/sodium formate system to produce aromatic monomers with a 36 mol % (in the case of stoichiometric oxidation) and 31 mol % (in the case of catalytic oxidation) yield (based on the original Klason lignin). The selectivity to a single product reached 80 % (syringyl propane dione, and 10–13 % to guaiacyl propane dione). These high yields of monomers and unprecedented selectivity are attributed to the preservation of the lignin structure by the acetal.

Design, synthesis and biological evaluation of flexible and rigid analogs of 4H-1,2,4-triazoles bearing 3,4,5-trimethoxyphenyl moiety as new antiproliferative agents

Ansari, Mahsa,Shokrzadeh, Mohammad,Karima, Saeed,Rajaei, Shima,Hashemi, Seyedeh Mahdieh,Mirzaei, Hassan,Fallah, Marjan,Emami, Saeed

, (2019/10/05)

Several flexible and rigid analogs of 4H-1,2,4-triazoles (compounds 8a-g and 9a-g) bearing trimethoxyphenyl pharmacophoric unit, were designed and synthesized as potential anticancer agents. The in vitro cytotoxic assay indicated that both flexible and rigid analogs (8 and 9, respectively) can potentially inhibit the growth of cancerous cells (A549, MCF7, and SKOV3), with IC50 values less than 5.0 μM. Furthermore, compounds 10a-l as regional isomers of compounds 9 exhibited remarkable cytotoxic activity with IC50 values ranging from 0.30 to 5.0 μM. The rigid analogs 9a, 10h and 10k were significantly more potent than etoposide against MCF7, SKOV3 and A549 cells, respectively. These compounds showed high selectivity towards cancer cells over normal cells, as they had no significant cytotoxicity against L929 cells. In addition, the representative compounds 9a and 10h could inhibit the tubulin polymerization at micro-molar levels. By determining changes in the colchicine-tubulin fluorescence, it was suggested that compound 10h could bind to the tubulin at the colchicine pocket. The molecular docking study further confirmed the inhibitory activity of promising compounds 9a, 10h and 10k on tubulin polymerization through binding to the colchicine-binding site.

N,N,N coordinated trivalent bicyclophosphide, synthetic method and catalytic application thereof

-

Paragraph 0047; 0048; 0049; 0050; 0053; 0059-0061; 0064, (2018/07/30)

The invention provides a N,N,N coordinated trivalent bicyclophosphide as an organic catalyst. The chemical structural formula of the compound is shown in the description. The final N,N,N coordinated trivalent bicyclophosphide is synthesized by adopting ketone as a raw material and multiple steps of bromination, ammoniation, reduction, imidization, hydrogenation and cyclization and the like in sequence. The N,N,N coordinated trivalent bicyclophosphide is characterized by synthesis of the N,N,N coordinated trivalent bicyclophosphide with an all-new structure and all-new synthetic route for preparing the phosphorus compound; simultaneously, the effective application of the N,N,N coordinated trivalent bicyclophosphide is successfully obtained, i.e., intramolecular aza Wittig reaction can be effectively catalyzed. Compared with the traditional transitional metal catalyst, the rare N,N,N coordinated trivalent bicyclophosphide has an obvious action in catalyzing an organic reaction system, and provides an all-new idea for the existing organic catalytic reaction. Compared with the traditional phosphine catalyst, the N,N,N coordinated trivalent bicyclophosphide has an obvious action in catalyzing the organic reaction system.

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