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7169-34-8 - 3-Coumaranone, 97% - 2H-Benzofuran-3-one - 2,3-Dihydrobenzofuran-3-one - A10202 - Alfa Aesar

A10202 3-Coumaranone, 97%

CAS Number
7169-34-8
Synonyms
2H-Benzofuran-3-one
2,3-Dihydrobenzofuran-3-one

Size Price ($) Quantity Availability
1g 47.28
5g 162.74
25g 531.20
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3-Coumaranone, 97%

MDL
MFCD00051810
EINECS
000-000-0

Chemical Properties

Formula
C8H6O2
Formula Weight
134.13
Melting point
97-102°
Sensitivity
Light Sensitive
Solubility
Slightly miscible with water.

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.

Notes

Light sensitive. Incompatible with strong oxidizing agents.

Literature References

3-Coumaranone and its substituted analogues undergo Horner-Wadsworth-Emmons reaction with Diethyl­ cyanomethyl­phosphonate, 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.

Other References

Beilstein
115296
Harmonized Tariff Code
2932.99
TSCA
No

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