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541-57-1 - Tetronic acid, 96% - 2,4(3H,5H)-Furandione - 4-Hydroxy-2(5H)-furanone - A14079 - Alfa Aesar

A14079 Tetronic acid, 96%

Numéro CAS
541-57-1
Synonymes
2,4(3H,5H)-Furandione
4-Hydroxy-2(5H)-furanone

Dimensions Prix ($) Quantité Disponibilité
5g 68,04
25g 279,13
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Tetronic acid, 96%

MDL
MFCD00010086
EINECS
208-785-3

Propriétés chimiques

Formule
C4H4O3
Poids formulaire
100.07
Point de fusion
ca 140° dec.
Solubilité
Soluble in water, dimethyl sulfoxide, acetonitrile and alcohol.

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.

Notes

Incompatible with strong oxidizing agents and strong alkalis (bases).

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Mentions de prudence: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
108442
Code tarifaire harmonisé
2932.20
TSCA
No

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Analytique et matériel de laboratoire