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Ethanone, 2-azido-1-(4-methoxyphenyl)-, also known as 2-azido-1-(4-methoxyphenyl)ethanone, is a chemical compound with the molecular formula C9H9N3O2. It is a derivative of acetophenone, characterized by a 2-azido substitution on the alpha carbon and a 4-methoxy substitution on the phenyl ring. This unique structure and the presence of functional groups make it a valuable building block in organic synthesis and medicinal chemistry research.

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  • 6595-28-4 Structure
  • Basic information

    1. Product Name: Ethanone, 2-azido-1-(4-methoxyphenyl)-
    2. Synonyms:
    3. CAS NO:6595-28-4
    4. Molecular Formula: C9H9N3O2
    5. Molecular Weight: 191.189
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 6595-28-4.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: N/A
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: Ethanone, 2-azido-1-(4-methoxyphenyl)-(CAS DataBase Reference)
    10. NIST Chemistry Reference: Ethanone, 2-azido-1-(4-methoxyphenyl)-(6595-28-4)
    11. EPA Substance Registry System: Ethanone, 2-azido-1-(4-methoxyphenyl)-(6595-28-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 6595-28-4(Hazardous Substances Data)

6595-28-4 Usage

Uses

Used in Organic Synthesis:
Ethanone, 2-azido-1-(4-methoxyphenyl)is used as a key intermediate in the synthesis of various organic compounds. Its azido and methoxy groups facilitate the formation of new chemical bonds and the creation of novel molecules with potential applications in different fields.
Used in Medicinal Chemistry Research:
Ethanone, 2-azido-1-(4-methoxyphenyl)is employed as a versatile building block in the development of pharmaceuticals and biologically active compounds. Its unique structure allows for the design and synthesis of new drug candidates with potential therapeutic applications.
Used in Drug Discovery:
Ethanone, 2-azido-1-(4-methoxyphenyl)is used as a starting material in the search for new drugs. Its functional groups can be modified to create molecules with specific biological activities, making it a valuable tool in the drug discovery process.
Used in Materials Science:
Ethanone, 2-azido-1-(4-methoxyphenyl)is used as a component in the development of new materials with unique properties. Its chemical structure can be incorporated into polymers, coatings, and other materials to enhance their performance and functionality.
Safety Precautions:
As with all chemical compounds, proper handling and safety precautions are necessary when working with Ethanone, 2-azido-1-(4-methoxyphenyl)-. This includes the use of appropriate personal protective equipment, working in a well-ventilated area, and following established safety protocols to prevent potential hazards and ensure safe usage.

Check Digit Verification of cas no

The CAS Registry Mumber 6595-28-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,5,9 and 5 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 6595-28:
(6*6)+(5*5)+(4*9)+(3*5)+(2*2)+(1*8)=124
124 % 10 = 4
So 6595-28-4 is a valid CAS Registry Number.

6595-28-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-azido-1-(4-methoxyphenyl)ethanone

1.2 Other means of identification

Product number -
Other names 2-azido-1-(4-methoxyphenyl)ethan-1-one

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

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More Details:6595-28-4 SDS

6595-28-4Relevant articles and documents

Microwave mediated synthesis of 2-aminooxazoles

Klug, Trevan,Cronin, Adam,O'Brien, Eli,Schioldager, Ryan,Johnson, Hunter,Gleason, Cameron,Schmid, Connor,Soderberg, Nathan,Manjunath, Aashrita,Liyanage, Duminda,Lazaro, Horacio,Kimball, Joshua J.,Eagon, Scott

supporting information, (2021/12/14)

A microwave mediated synthesis of 2-aminooxazoles at 150 °C was developed, providing products with a variety of functional groups. The reaction takes 5 min and provides product with a simple precipitation at moderate to good yields without the need for recrystallization or flash chromatography.

Indole-linked 1,2,3-triazole derivatives efficiently modulate COX-2 protein and PGE2 levels in human THP-1 monocytes by suppressing AGE-ROS-NF-kβ nexus

Aslam, Tooba,Basha, Fatima Z.,Choudhary, M. Iqbal,Iqbal, Shazia,Jahan, Humera,Khan, Maria Aqeel,Siddiqui, Nimra Naz

, (2022/01/19)

Aims: AGEs augment inflammatory responses by activating inflammatory cascade in monocytes, and hence lead to vascular dysfunction. The current study aims to study a plausible role and mechanism of a new library of indole-tethered 1,2,3-triazoles 2-13 in A

Visible-light-induced N-heterocyclic carbene mediated cascade transformation of N-alkenoxypyridinium salts

Chen, Fei,Chen, Xiangyu,Liu, Qiang,Sheng, He,Wang, Zhixiang

supporting information, (2022/02/02)

While N-alkenoxypyridinium salts are widely used for the synthesis of α-functionalized ketones via umpolung strategy, such approaches are usually limited to special nucleophiles at high temperatures. Herein, we developed an alternative photoinduced N-heterocyclic carbene (NHC)- mediated functionalization of N-alkenoxypyridinium salts with various nucleophiles, including tetramethylammonium azide, secondary amines, aryl and alkyl thiols, and even the challenging C(sp3)-nucleophiles, under mild conditions. A cascade radical-radical coupling/nucleophilic substitution sequence was proposed, wherein the NHC enabled the formation of a photoactive electron donor-acceptor complex for α-iodo ketone synthesis.

First synthesis of tabamides A–C and their derivatives: In vitro nitric oxide inhibitory activity

Damodar, Kongara,Shin, Sooyong,Jeon, Sung Ho,Lee, Jeong Tae

, (2021/11/10)

The first synthesis of natural phenolic amides, tabamides A–C (1–3), and their derivatives (4–12) was accomplished using Stobbe condensation and amide coupling reactions as key steps. The in vitro nitric oxide (NO) inhibitory effects of these compounds in LPS-induced RAW-264.7 macrophages were evaluated as an indicator of anti-inflammatory activity. All compounds tested had a concentration-dependent inhibitory effect on NO production by RAW-264.7 macrophages without significant cytotoxicity. Compound 6, a tabamide A derivative (IC50 = 82.6 μM), followed by tabamide A (1, IC50 = 100.7 μM), was the most potent from the series. The present study revealed that tabamide A (1) could be considered as a lead structure to develop NO production-targeted anti-inflammatory agents.

Electrochemical Difunctionalization of Styrenes via Chemoselective Oxo-Azidation or Oxo-Hydroxyphthalimidation

Jiang, Haobin,Wang, Feng,Ye, Zenghui,Zhang, Fengzhi,Zhu, Rongjin

supporting information, p. 8240 - 8245 (2021/11/17)

Atom- and step-economic oxo-azidation and oxo-hydroxyphthalimidation of styrenes have been developed under mild electrolytic conditions, respectively. Various valuable alpha-azido or hydroxyphthalimide aromatic ketones were synthesized efficiently from readily available styrenes, azides, and N-hydroxyphthalimides. Mechanism studies show that two different pathways involved in these two transformations.

Discovery of triazolyl thalidomide derivatives as anti-fibrosis agents

Tang, Kai-Wei,Hsu, Wen-Li,Chen, Cheng-Ru,Tsai, Ming-Hsien,Yen, Chia-Jung,Tseng, Chih-Hua

, p. 3589 - 3599 (2021/03/03)

Fibrosis with excessive accumulation of extracellular matrix (ECM) often causes progressive organ dysfunction and results in many inflammatory and metabolic diseases, including systemic sclerosis, pulmonary fibrosis, advanced liver disease and advanced kidney disease. The store-operated calcium entry (SOCE) pathway and the related signaling pathway were both found to be the important routes for fibrogenesis. Our aim in this study was to discover novel compounds to inhibit fibrogenesis. A number of triazolyl thalidomide derivatives were synthesized and evaluated for their anti-fibrosis activities. Compounds 7b-e, 8c-d, 10a-b and 10e inhibited intracellular Ca2+ activation and showed no cytotoxicity. Among them, 6-{4-[(3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}hexanoic acid (10e) with the most potent inhibitory effect was chosen for further examination. The results revealed that compound 10e, a SOCE inhibitor, reversed the migratory ability of TGF-β1-induced myofibroblasts, dedifferentiated myofibroblasts to fibroblasts due to cytoskeleton remodeling, and restrained myofibroblast activation by targeting Orai1 and TGF-β1/SMAD2/3 signaling pathways. The in silico study indicated that compound 10e, with the appropriate lipophilic carbon chain and carboxylic acid, showed a good drug-likeness model score. Conclusively, the SOCE inhibitor, compound 10e, is used as a promising lead compound for the development of a new treatment for fibrosis. This journal is

New 2,9-disubstituted-1,10-phenanthroline derivatives with anticancer activity by selective targeting of telomeric G-quadruplex DNA

Craciun, Anda-Mihaela,Rotaru, Alexandru,Cojocaru, Corneliu,Mangalagiu, Ionel I.,Danac, Ramona

, (2021/01/18)

Fifteen new 1,10-phenanthrolines disubstituted at positions 2 and 9 via amide bonds with different heterocycles have been designed and synthesized as G-quadruplex DNA stabilizers. Ten compounds were evaluated for the in vitro anticancer activity against 60 human tumor cell lines panel, four of them showing a very good inhibitory activity on several cell lines. To assess the ability of the most active compounds to interact with G-quadruplex DNA (G4-DNA), circular dichroism experiments were performed. The potency of the compounds to stabilize the G4-DNA has been shown from the thermal denaturation experiments. The mechanism of compounds binding to DNA and to G4-DNA was theoretically investigated by molecular docking studies. The experimental results demonstrated excellent capacity of the two compounds bearing two pyridin-3-yl residues (methylated and non-methylated) to act as selective G-quadruplex binders with promising anticancer activity.

Novel series of triazole containing coumarin and isatin based hybrid molecules as acetylcholinesterase inhibitors

Bedi, Preet Mohinder Singh,Bhagat, Kavita,Gulati, Harmandeep Kaur,Kaur, Arshmeet,Kumar, Nitish,Sharma, Aakriti,Singh, Atamjit,Singh, Harbinder,Singh, Jatinder Vir

, (2021/07/28)

Novel series of coumarin-triazole and isatin-triazole hybrids were rationally designed, synthesized and biologically evaluated to check their inhibitory potential against acetylcholinesterase enzyme by using in vitro Ellman's method. Most of the hybrid compounds showed significant inhibition against the enzyme. Biological assay revealed that compound B-1 (among 4-hydroxycoumarin-triazole series) and compound AS-8 (from isatin-triazole series) possessed potent inhibitory activity against the AChE with the IC50 values of 110 ± 1.11 nM and 155 ± 1.65 nM, respectively. These active compounds (B-1 and AS-8) exhibited mixed mode of enzyme's inhibition which was confirmed through enzyme kinetic studies. Molecular docking studies were performed to understand the binding modes of these potent compounds within the active pocket of AChE enzyme by using Discovery studio. Furthermore, to predict the stability of the most prominent compound B-1 within the catalytic cavity of AChE, molecular dynamic simulations were performed for 5 ns and was found that ligand and protein complex is stable within their dynamic system. Therefore, these hybrids could be taken as effective lead candidates for further designing, development and optimization of new acetylcholinesterase inhibitors.

N-transfer reagent and method for preparing the same and its application

-

Page/Page column 21-22, (2021/06/25)

Provided are a novel N-transfer reagent and a method for preparing the same and its application. The N-transfer reagent is represented by the following Formula (I): The various novel N-transfer reagents of the present invention can be quickly prepared by employing different nitrobenzene precursors. The N-transfer reagents can directly convert a variety of amino compounds into diazo compounds under mild conditions. Particularly, the N-transfer reagents can facilitate the synthesis of the diazo compounds. The application of synthesizing diazo compounds of the present invention can greatly decrease the difficulty in operation, increase the safety during experiments, reduce the cost of production and the environmental pollution, and enhance the industrial value of diazo compounds.

Stereoselective synthesis of (Z)-1,3-bis(α,β-unsaturated carbonyl)-isoindolines from aldehydes and phenacyl azides under metal free conditions

Prasad, Budaganaboyina,Phanindrudu, Mandalaparthi,Nanubolu, Jagadeesh Babu,Kamal, Ahmed,Tiwari, Dharmendra Kumar

supporting information, p. 9542 - 9545 (2021/09/28)

Here in the present manuscript, we report our observation of an unprecedented stereoselective synthesis of 2H-isoindolin-1,3-ylidenes from 2-(formylphenyl)acrylates and phenacylazide in the presence of piperidine. Unlike in our previous findings, in which

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