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Sigma-Aldrich

α-Methylene-γ-butyrolactone

97%

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Synonym(s):
alpha-Methylene-gamma-butyrolactone, 3-Methylenedihydro-2(3H)-furanone, Tulipane
Empirical Formula (Hill Notation):
C5H6O2
CAS Number:
Molecular Weight:
98.10
Beilstein:
107939
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

liquid

contains

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

refractive index

n20/D 1.472 (lit.)

bp

86-88 °C/12 mmHg (lit.)

solubility

water: soluble(lit.)

density

1.119 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C=C1CCOC1=O

InChI

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

InChI key

GSLDEZOOOSBFGP-UHFFFAOYSA-N

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1 of 4

This Item
11775755201444286
form

liquid

form

-

form

solid

form

liquid

refractive index

n20/D 1.472 (lit.)

refractive index

n20/D 1.432 (lit.)

refractive index

-

refractive index

n20/D 1.467 (lit.)

bp

86-88 °C/12 mmHg (lit.)

bp

78-81 °C/10 mmHg (lit.)

bp

-

bp

133 °C/10 mmHg (lit.)

solubility

water: soluble(lit.)

solubility

THF: soluble

solubility

H2O: 1 g/10 mL, clear, colorless to almost colorless

solubility

-

density

1.119 g/mL at 25 °C (lit.)

density

-

density

-

density

1.309 g/mL at 25 °C (lit.)

Application

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.

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

98.6 °F - closed cup

Flash Point(C)

37 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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Customers Also Viewed

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1 of 6

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.
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
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
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
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.

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