Search
元素の検索
構造の検索
Thermo Scientific Chemicals
Tetronic acid, 96%
CAS: 541-57-1 | C4H4O3 | 100.07 g/mol
化学物質識別子
CAS541-57-1
IUPAC Name4-hydroxy-2,5-dihydrofuran-2-one
Molecular FormulaC4H4O3
InChI KeyJZQBAGOECGRTSA-UHFFFAOYSA-N
SMILESOC1=CC(=O)OC1
さらに表示
仕様
スペックシート
スペックシートAppearance (Color)White to cream to yellow
FormCrystals or powder or crystalline powder
Assay (Aqueous acid-base Titration)≥95.0 to ≤105.0%
Identification (FTIR)Conforms
Tetronic acid is used as a precursor of a variety of substituted and ring-fused furans and butenolides. It is an acidic building block for heterocyclic compounds for medicinal applications. It is used for selective O-alkyaltion reactions involving cesium fluoride. It is also used to prepare 3H-furo[3,4-b]quinolin-1-one by reacting with 2-amino-benzaldehyde.
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
Tetronic acid is used as a precursor of a variety of substituted and ring-fused furans and butenolides. It is an acidic building block for heterocyclic compounds for medicinal applications. It is used for selective O-alkyaltion reactions involving cesium fluoride. It is also used to prepare 3H-furo[3,4-b]quinolin-1-one by reacting with 2-amino-benzaldehyde.
Solubility
Soluble in water, dimethyl sulfoxide, acetonitrile and alcohol.
Notes
Incompatible with strong oxidizing agents and strong alkalis (bases).
Tetronic acid is used as a precursor of a variety of substituted and ring-fused furans and butenolides. It is an acidic building block for heterocyclic compounds for medicinal applications. It is used for selective O-alkyaltion reactions involving cesium fluoride. It is also used to prepare 3H-furo[3,4-b]quinolin-1-one by reacting with 2-amino-benzaldehyde.
Solubility
Soluble in water, dimethyl sulfoxide, acetonitrile and alcohol.
Notes
Incompatible with strong oxidizing agents and strong alkalis (bases).
RUO – Research Use Only
General References:
- Equivalent to the -lactone of 4-hydroxyacetoacetic acid.
- Selective O-alkylation is promoted by CsF under mild conditions: Synlett, 843 (1995).
- Versatile precursor of a variety of substituted and ring-fused furans and butenolides; see, e.g.: J. Org. Chem., 48, 1914 (1983); Synthesis, 155 (1996).
- Li, X. K.; Xiong, F.; Shen, Z. Y.; Zhang, S. P.; Zhou, Y. H.; Xu, M. L.; Zhou, Z. Q. Unexpected Facile Synthesis of Tetronic Acid During the Research on Stereospecific Total Synthesis of (+)-Biotin Starting from D-Erythorbic Acid as Chiral Pool. Asian J. Chem. 2015, 27 (5), 1957.
- Chopin, N.; Yanai, H.; Likawa, S.; Pilet, G.; Bouillon, J. P.; Médebielle, M. A Rapid Entry to Diverse gamma-Ylidenetetronate Derivatives through Regioselective Bromination of Tetronic Acid Derived gamma-Lactones and Metal-Catalyzed Postfunctionalization. Eur. J. Org. Chem. 2015, 2015 (28), 6259-6269.