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3-Coumaranone, 97%, Thermo Scientific Chemicals
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Catalog number A10202.06
also known as A10202-06
Price (USD)/ Each
213.00
-
Quantity:
5 g
Price (USD)/ Each
213.00
3-Coumaranone, 97%, Thermo Scientific Chemicals
Catalog numberA10202.06
Price (USD)/ Each
213.00
-
Chemical Identifiers
CAS7169-34-8
Specifications
Specification Sheet
Specification SheetMelting Point (clear melt)95.0-104.0?C
Assay (GC)≥96.0%
Appearance (Color)Yellow to orange
FormPowder
3-Coumaranone is used in the aurones, [2-benzylidenebenzofuran-3(2H)-ones] by reacting with appropriate aldehyde. It is involved in the condensation reaction with aldehydes in the presence of morpholine acetate to prepare substituted 2-(arylidene)benzofuran-3(ZH)-ones. In Horner-Wadsworth-Emmons reaction, it reacts with diethyl¬ cyanomethyl¬phosphonate to give 3-(cyanomethyl)benzofurans, which is an intermediate in the synthesis of antihyperglycemic agents.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
3-Coumaranone is used in the aurones, [2-benzylidenebenzofuran-3(2H)-ones] by reacting with appropriate aldehyde. It is involved in the condensation reaction with aldehydes in the presence of morpholine acetate to prepare substituted 2-(arylidene)benzofuran-3(ZH)-ones. In Horner-Wadsworth-Emmons reaction, it reacts with diethyl¬ cyanomethyl¬phosphonate to give 3-(cyanomethyl)benzofurans, which is an intermediate in the synthesis of antihyperglycemic agents.
Solubility
Slightly miscible with water.
Notes
Light sensitive. Incompatible with strong oxidizing agents.
3-Coumaranone is used in the aurones, [2-benzylidenebenzofuran-3(2H)-ones] by reacting with appropriate aldehyde. It is involved in the condensation reaction with aldehydes in the presence of morpholine acetate to prepare substituted 2-(arylidene)benzofuran-3(ZH)-ones. In Horner-Wadsworth-Emmons reaction, it reacts with diethyl¬ cyanomethyl¬phosphonate to give 3-(cyanomethyl)benzofurans, which is an intermediate in the synthesis of antihyperglycemic agents.
Solubility
Slightly miscible with water.
Notes
Light sensitive. Incompatible with strong oxidizing agents.
RUO – Research Use Only
General References:
- 3-Coumaranone and its substituted analogues undergo Horner-Wadsworth-Emmons reaction with Diethyl cyanomethyl phosphonate, A10218, in the presence of NaH, to give 3-(cyanomethyl)benzofurans, intermediates in a synthesis of antihyperglycemic agents: J. Med. Chem., 35, 1176 (1992).
- Condenses with aromatic aldehydes in the presence of alumina under mild conditions to give aurones, an important class of natural pigments: Tetrahedron Lett., 33, 5937 (1992):
- Shu, C.; Liu, R.; Liu, S.; Li, J.; Yu, Y.; He, Q.; Lu, X.; Ye, L. Practical, Modular, and General Synthesis of 3-Coumaranones through Gold-Catalyzed Intermolecular Alkyne Oxidation Strategy. Chem. Asian J. 2015, 10 (1), 91-95.
- Kuppusamy, R.; Gandeepan, P.; Cheng, C. RhIII-Catalyzed [4 + 1] Annulations of 2-Hydroxy- and 2-Aminobenzaldehydes with Allenes: A Simple Method toward 3-Coumaranones and 3-Indolinones. Org. Lett. 2015, 17 (15), 3846-3849.