226416
α-Methylene-γ-butyrolactone
97%
Synonym(s):
alpha-Methylene-gamma-butyrolactone, 3-Methylenedihydro-2(3H)-furanone, Tulipane
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About This Item
Empirical Formula (Hill Notation):
C5H6O2
CAS Number:
Molecular Weight:
98.10
NACRES:
NA.22
UNSPSC Code:
12352100
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
107939
Assay:
97%
Form:
liquid
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.)
functional group
ester
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
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.
signalword
Warning
hcodes
Hazard Classifications
Aquatic Chronic 3 - Flam. Liq. 3 - Skin Sens. 1
Storage Class
3 - Flammable liquids
flash_point_f
98.6 °F - closed cup
flash_point_c
37 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
危险化学品
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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.
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 226416-1G | 04061838780201 |
| 226416-5G | 04061838780218 |