α-Methylene-γ-butyrolactone
Product Information
Molecular Formula
C5H6O2
Molecular Weight
98.10
Description
α-Methylene-γ-butyrolactone (CAS# 547-65-9) is a useful research chemical.
Synonyms
3-methylideneoxolan-2-one
IUPAC Name
3-methylideneoxolan-2-one
SMILES
C=C1CCOC1=O
InChI
InChI=1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2
InChI Key
GSLDEZOOOSBFGP-UHFFFAOYSA-N
Boiling Point
90 °C / 13 mmHg
Flash Point
90 °C
Purity
> 95.0 % (GC)
Density
1.119 g/mL at 25 °C(lit.)
Appearance
Colorless to light yellow clear liquid
Storage
0-10 °C
Refractive Index
n20/D 1.472(lit.)
LogP
0.48950
Safety Information
Hazards
H315:
Causes skin irritation.
H317:
May cause an allergic skin reaction.
H319:
Causes serious eye irritation.
H334:
May cause allergy or asthma symptoms or breathing difficulties if inhaled.
Causes skin irritation.
H317:
May cause an allergic skin reaction.
H319:
Causes serious eye irritation.
H334:
May cause allergy or asthma symptoms or breathing difficulties if inhaled.
Precautionary Statement
P210, P233, P240, P241, P242, P243, P261, P272, P280, P302+P352, P303+P361+P353, P321, P333+P313, P363, P370+P378, P403+P235, and P501
Signal Word
Warning
Computed Properties
XLogP3
0.8
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
0
Exact Mass
98.036779430 g/mol
Monoisotopic Mass
98.036779430 g/mol
Topological Polar Surface Area
26.3Ų
Heavy Atom Count
7
Formal Charge
0
Complexity
115
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| CN-114106044-A | Binuclear pyridine phosphine base, full-acrylate thermoplastic elastomer and preparation method thereof | 2021-12-07 |
| CN-113968833-A | Phenol derivative containing alpha-methylene-gamma-butyrolactone structure, preparation method and application thereof | 2021-12-03 |
| CN-114031582-A | Alpha-hydroxy-gamma-butyrolactone compound, preparation method and application thereof | 2021-12-03 |
| CN-113583043-A | Strong-nucleophilicity organic phosphine compound for polar vinyl monomer polymerization, preparation method and application thereof | 2021-07-28 |
| KR-102295075-B1 | Composition for controlling agricultural pest comprising Tulipalin A as effective component | 2021-06-22 |
| KR-102279773-B1 | Composition for controlling stored product insect comprising Tulipalin A as effective component | 2021-05-11 |
| CN-112961268-A | Method for synthesizing renewable TPEs (thermoplastic polyurethanes) through FLP (flash polymerization) catalysis based on bifunctional phosphine base | 2021-02-26 |
| CN-112961268-B | Method for synthesizing renewable TPEs (thermoplastic polyurethanes) through FLP (flash polymerization) catalysis based on bifunctional phosphine base | 2021-02-26 |
| CN-112625292-A | Preparation method of degradable shape memory polymer medical splint | 2020-12-17 |
| CN-112625180-A | Uvioresistant microsphere, preparation method and application | 2020-12-07 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 22985027 | 2012-10-25 | Guaianolide sesquiterpene lactones, a source to discover agents that selectively inhibit acute myelogenous leukemia stem and progenitor cells | Journal of medicinal chemistry |
| 22734694 | 2012-07-11 | Enantioselective conversion of primary alcohols to α-exo-methylene γ-butyrolactones via iridium-catalyzed C-C bond-forming transfer hydrogenation: 2-(alkoxycarbonyl)allylation | Journal of the American Chemical Society |
| 22217935 | 2012-07-01 | Allergic contact dermatitis to plants: understanding the chemistry will help our diagnostic approach | Actas dermo-sifiliograficas |
| 22526727 | 2012-05-28 | Zinc or indium-mediated Barbier-type allylation of aldehydes with 3-bromomethyl-5H-furan-2-one in aqueous media: an efficient synthesis method for α-methylene-γ-butyrolactone | Organic & biomolecular chemistry |
| 22247601 | 2012-01-01 | Okanin, a chalcone found in the genus Bidens, and 3-penten-2-one inhibit inducible nitric oxide synthase expression via heme oxygenase-1 induction in RAW264.7 macrophages activated with lipopolysaccharide | Journal of clinical biochemistry and nutrition |
| 22070869 | 2011-12-02 | An allenic Pauson-Khand approach to 6,12-guaianolides | Organic letters |
| 21620534 | 2011-08-01 | Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents | European journal of medicinal chemistry |
| 21517115 | 2011-06-13 | Free radical copolymerization kinetics of γ-methyl-α-methylene-γ-butyrolactone (MeMBL) | Biomacromolecules |
| 21488628 | 2011-05-20 | Stereoselective synthesis of β-(hydroxymethylaryl/alkyl)-α-methylene-γ-butyrolactones | Organic letters |
| 21113170 | 2011-01-01 | Selective irreversible inhibition of a protease by targeting a noncatalytic cysteine | Nature chemical biology |
