163684-51-3

Basic information

• Product Name: 4-(chloromethyl)-6-methoxy-2H-chromen-2-one
• Synonyms: 4-(chloromethyl)-6-methoxy-2H-chromen-2-one;4-(chloromethyl)-6-methoxy-2-chromenone;4-(chloromethyl)-6-methoxy-chromen-2-one;4-(chloromethyl)-6-methoxychromen-2-one;4-(chloromethyl)-6-methoxy-coumarin
• CAS NO: 163684-51-3
• Molecular Formula: C11H9ClO3
• Molecular Weight: 224.64036
• Mol File: 163684-51-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 384.167°C at 760 mmHg
• Flash Point: 171.246°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: 4-(chloromethyl)-6-methoxy-2H-chromen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(chloromethyl)-6-methoxy-2H-chromen-2-one(163684-51-3)
• EPA Substance Registry System: 4-(chloromethyl)-6-methoxy-2H-chromen-2-one(163684-51-3)

Safety Data

• Hazardous Substances Data: 163684-51-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H9ClO3/c1-14-8-2-3-10-9(5-8)7(6-12)4-11(13)15-10/h2-5H,6H2,1H3

Upstream product

• 150-76-5 4-methoxy-phenol 
• 123-11-5 4-methoxy-benzaldehyde 
• 638-07-3 ethyl (2-chloroaceto)acetate 

Relevant articles and documents

Synthesis of 4-aryl-1,2,3-triazolyl appended natural coumarin-related compounds with antiproliferative and radical scavenging activities and intracellular ROS production modification

Novel natural coumarin-based umbelliferone, herniarin and esculetin series linked to hydroxy- and methoxy-substituted and non-substituted phenyl rings through a 1,2,3-triazole spacer were provided by environmentally friendly click chemistry under microwave irradiation. The antioxidative activity of the compounds was evaluated by DPPH-scavenging activity and cyclic voltammetry assays. While adjacent 6- and 7-hydroxyl groups in coumarins made a major contribution to antioxidative power and a decrease of ROS production relative to esculetin, a p-methoxy-substituted phenyl moiety had an impact on pronounced and selective antiproliferative activity against chronic leukemia cells in blast crisis (K562) with no significant change in the ROS generation. 6,7-Dihydroxycoumarin can be considered as a promising scaffold with a major contribution to antioxidant potential and, thereby, further structural modification of 6,7-dihydroxycoumarin linked to aryl-1,2,3-triazole may provide a hybrid molecule that may be of interest for potential application to prevent diseases related to the oxidative-stress imbalance.

Design and synthesis of tailored human caseinolytic protease P inhibitors

Human caseinolytic protease P (hClpP) is important for degradation of misfolded proteins in the mitochondrial unfolded protein response. We here introduce tailored hClpP inhibitors that utilize a steric discrimination in their core naphthofuran scaffold to selectively address the human enzyme. This novel inhibitor generation exhibited superior activity compared to previously introduced beta-lactones, optimized for bacterial ClpP. Further insights into the bioactivity and binding to cellular targets were obtained via chemical proteomics as well as proliferation- and migration studies in cancer cells.

A CONVENIENT SYNTHESIS OF BENZOFURAN-3-ACETIC ACIDS

We describe a two-step synthesis of benzofuran-3-acetic acids (1) from phenols (2) involving alkali-mediated rearrangement of 4-halomethylcoumarins (3) via α,β-unsaturated acids (4).Electron-donating substituents at the meta position of the phenol favour high yields of the coumarin, which in all cases rearranges to afford benzofuran-3-acetic acids in near quantitative yields.