14071-69-3

Basic information

• Product Name: 2H-1-Benzopyran-2-one, 3-(4-methylphenyl)-
• CAS NO: 14071-69-3
• Molecular Formula: C16H12O2
• Molecular Weight: 236.27
• Mol File: 14071-69-3.mol
• Article Data: 25

Chemical Properties

• CAS DataBase Reference: 2H-1-Benzopyran-2-one, 3-(4-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1-Benzopyran-2-one, 3-(4-methylphenyl)-(14071-69-3)
• EPA Substance Registry System: 2H-1-Benzopyran-2-one, 3-(4-methylphenyl)-(14071-69-3)

Safety Data

• Hazardous Substances Data: 14071-69-3(Hazardous Substances Data)

Upstream product

• 93696-60-7 3-Bromo-4-p-tolyl-chroman-2-one 
• 622-47-9 4-tolylacetic acid 
• 446-52-6 2-Fluorobenzaldehyde 
• 90-02-8 salicylaldehyde 
• 91-64-5 coumarin 
• 98-59-9 p-toluenesulfonyl chloride 
• 108-88-3 toluene 
• 766-97-2 4-n-methylphenylacetylene 
• 637-60-5 p-tolylhydrazine hydrochloride 
• 50978-45-5 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide 
• 104-82-5 4-Methylbenzyl chloride 
• 99-94-5 p-Toluic acid 
• 106-49-0 p-toluidine 
• 1333483-18-3 N-methyl-N-(p-tolylethynyl)methanesulfonamide 

Downstream Products

• 59583-83-4 4-(2-oxo-2H-chromen-3-yl)benzaldehyde 
• 1337918-42-9 C₄₆H₄₁BF₂N₄O₂ 
• 1337918-41-8 C₄₄H₃₅BF₂N₂O₄ 

Relevant articles and documents

Direct C-3 alkylation of coumarins via decarboxylative coupling with carboxylic acids

A new method for selective C-3 alkylation of coumarins using carboxylic acids as alkyl sources is reported. This process offers a practical method for the facile construction of 3-alkyl coumarins with a broad substrate scope. The reaction works under metal-free and aqueous media and both cyclic and acyclic aliphatic carboxylic acids participate in this radical C-C cross coupling reaction.

Facile one-pot synthetic access to libraries of diversely substituted 3-aryl (Alkyl)-coumarins using ionic liquid (IL) or conventional base/solvent, and an IL-mediated approach to novel coumarin-bearing diaryl-ethynes

The in-situ formed carbonylimidazole derivatives of Ar(alkyl)-CH2COOH react at r.t. with substituted salicylaldehydes in [BMIM][PF6] or [BMIM][BF4] as solvent, and [PAIM][NTf2] as basic-IL, to produce libraries of 3-aryl(alkyl)coumarins. Whereas these reactions can also be performed with similar efficiency in THF by employing DBU, the IL approach offers easier work-up and recycling of the IL solvent. An IL-mediated approach to the synthesis of novel coumarin-bearing diaryl-ethynes by the Sonogshira reaction is also reported, and the potential for recycling/reuse of the IL solvent is shown.

Visible-light-driven copper-catalyzed aerobic oxidative cascade cyclization of N-tosylhydrazones and terminal alkynes: Regioselective synthesis of 3-arylcoumarins

We present the first example of sustainable, intuitive, highly regioselective, visible-light-driven copper catalyzed aerobic oxidative cascade cyclization of N-tosylhydrazones with terminal alkynes for the preparation of 3-arylcoumarins at room temperature. This operationally simple methodology has been successfully applied to a wide range of N-tosylhydrazones and alkynes (49 examples), and proceeds well to afford biologically active compounds, such as monoamine oxidase B (MAO-B) inhibitor and horseradish peroxidase (HRP) inhibitor, in satisfactory yields under mild conditions. Furthermore, mechanistic studies suggest that the reaction proceeds via a copper(ii)-superoxo or -peroxo complex mediated oxidative annulation of terminal alkynes, as evidenced by 18O2 isotopic-labelling experiments.