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
Canonical 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 ℃ / 13 mmHg
Flash Point
90 ℃
Purity
> 95.0 % (GC)
Density
1.119 g/mL at 25 ℃(lit.)
Appearance
Colorless to light yellow clear liquid
Storage
0-10 ℃
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.
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
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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