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Merck

226416

Sigma-Aldrich

α-Methylene-γ-butyrolactone

97%

Sinónimos:

alpha-Methylene-gamma-butyrolactone, 3-Methylenedihydro-2(3H)-furanone, Tulipane

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About This Item

Fórmula empírica (notación de Hill):
C5H6O2
Número de CAS:
Peso molecular:
98.10
Beilstein:
107939
Número MDL:
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
NACRES:
NA.22

Nivel de calidad

Ensayo

97%

Formulario

liquid

contiene

~2% 2,6-di-tert-butyl-p-cresol as stabilizer

índice de refracción

n20/D 1.472 (lit.)

bp

86-88 °C/12 mmHg (lit.)

solubilidad

water: soluble(lit.)

densidad

1.119 g/mL at 25 °C (lit.)

grupo funcional

ester

temp. de almacenamiento

2-8°C

cadena SMILES

C=C1CCOC1=O

InChI

1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2

Clave InChI

GSLDEZOOOSBFGP-UHFFFAOYSA-N

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Aplicación

α-Methylene-γ-butyrolactone (Tulipane) was used to develop optically active spiro-[butyrolactone-pyrrolidine] via Cu(I)-catalyzed exo-selective 1,3-dipolar cycloaddition of azomethine ylides.

Pictogramas

FlameExclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

Aquatic Chronic 3 - Flam. Liq. 3 - Skin Sens. 1

Código de clase de almacenamiento

3 - Flammable liquids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

98.6 °F - closed cup

Punto de inflamabilidad (°C)

37 °C - closed cup

Equipo de protección personal

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Qing-Hua Li et al.
Chemical communications (Cambridge, England), 49(83), 9642-9644 (2013-09-12)
An expedient access to optically active spiro-[butyrolactone-pyrrolidine] was successfully developed via an unprecedented Cu(I)-catalyzed exo-selective 1,3-DC of azomethine ylides with α-methylene-γ-butyrolactone, which exhibited high diastereoselectivity (>98 : 2), excellent enantioselectivity (96->99% ee) and a broad substrate scope under mild conditions.
Sébastien Fuchs et al.
Photochemistry and photobiology, 86(3), 545-552 (2010-02-02)
(+) and (-) alpha-methylene-hexahydrobenzofuranone derivatives with a stereochemically pure cis ring junction were used as models of sesquiterpene lactones to study their photoreactivity toward thymidine. After 313 nm irradiation of a deoxygenated acetone solution of lactone models and thymidine, six
Francesca Cateni et al.
European journal of medicinal chemistry, 41(2), 192-200 (2005-12-22)
The synthesis of a series of alpha-methylene-gamma-butyrolactones (compounds 4a, 4b, 6-12, 16, 17) and alpha,beta-unsaturated-delta-lactones (compounds 19-23, 25, 26) starting from 4,4-dimethyldihydrofuran-2,3-dione (1) has been described. Their chemical structures were assigned by spectroscopic evidence. These new compounds exhibited significantly different
YuZhe Gao et al.
Organic & biomolecular chemistry, 10(20), 3991-3998 (2012-04-25)
A zinc or indium-mediated Barbier-type allylation of aldehydes with 3-bromomethyl-5H-furan-2-one in aqueous solvents was developed to provide an efficient route to α-methylene-γ-butyrolactone, which is synthetically very useful. The desired products were obtained in moderate to high yields in aqueous solvents.
E Rozas-Muñoz et al.
Actas dermo-sifiliograficas, 103(6), 456-477 (2012-01-06)
Allergic contact dermatitis due to plants is common. Potentially allergenic plants and plant products are found in many everyday environments, such as the home, the garden, the workplace, and recreational settings. By improving our knowledge of allergenic plant-derived chemical compounds

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