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283754

Sigma-Aldrich

2(5H)-Furanone

98%

Synonyme(s) :

γ-Crotonolactone, 2-Buten-1,4-olide

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1 G
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About This Item

Formule empirique (notation de Hill) :
C4H4O2
Numéro CAS:
Poids moléculaire :
84.07
Beilstein:
383585
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352100
ID de substance PubChem :
Nomenclature NACRES :
NA.22

80.90 CHF


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Essai

98%

Forme

liquid

Indice de réfraction

n20/D 1.469 (lit.)

pb

86-87 °C/12 mmHg (lit.)

Pf

4-5 °C (lit.)

Densité

1.185 g/mL at 25 °C (lit.)

Groupe fonctionnel

ester

Température de stockage

2-8°C

Chaîne SMILES 

O=C1OCC=C1

InChI

1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2

Clé InChI

VIHAEDVKXSOUAT-UHFFFAOYSA-N

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Description générale

Chiral urea compounds catalyzed hetero-Michael addition reaction of 2(5H)-furanone (γ-crotonolactone) to pyrrolidine[1]. The quorum sensing inhibition activity by 2(5H)-furanone was studied using bioindicator strains[2].

Application

2(5H)-Furanone (γ-Crotonolactone) has been used in:
  • synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid[3]
  • synthesis of 5-substituted 2(5H) furanones (γ-butenolides) via direct aldol reaction with aromatic aldehydes catalyzed by bifunctional aminothiourea and aminosquaramide organocatalysts[4]
  • Michael addition reactions[5] for synthesis of lignans[6]
  • three-component Michael-Aldol reactions with an aldehyde anda thiolate[7] or carbanion[8]

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

213.8 °F - closed cup

Point d'éclair (°C)

101 °C - closed cup

Équipement de protection individuelle

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Certificats d'analyse (COA)

Lot/Batch Number

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Les clients ont également consulté

Yoshihiro Sohtome et al.
Chemical & pharmaceutical bulletin, 52(4), 477-480 (2004-04-02)
Chiral urea compounds 10a-g were synthesized as catalysts for conjugate addition of pyrrolidine (2) to gamma-crotonolactone (3). In the presence of a catalytic amount of the chiral ureas, this hetero-Michael reaction was greatly accelerated. Asymmetric induction was observed with the
Tetrahedron, 49, 4173-4173 (1993)
Tetrahedron, 49, 9039-9039 (1993)
Tetrahedron, 49, 8073-8073 (1993)
Sunil V Pansare et al.
Organic & biomolecular chemistry, 10(10), 2119-2125 (2012-02-02)
The γ-butenolide obtained from an organocatalyzed, direct vinylogous aldol reaction of γ-crotonolactone and benzaldehyde serves as the key starting material in the expedient synthesis of a 3-hydroxy-2-phenyl piperidine intermediate which is converted to the target 2,3-disubstituted piperidines.

Questions

1–2 of 2 Questions  
  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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