3-Methylenedihydro-2(3H)-furanone

Basic Information

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CAS Number

547-65-9

Molecular Formula

C5H6O2

Molecular Weight

98.1 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Water Treatment Chemicals Coagulants and Flocculants Inorganic Coagulants

Basic Physical Properties

Melting Point

No data available

Boiling Point

86-88 °C/12 mmHg

Solubility

water: soluble(lit.)

Refractive Index

n20/D 1.472(lit.)

SMILES

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C=C1CCOC1=O

InChI

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

InChIKey

GSLDEZOOOSBFGP-UHFFFAOYSA-N

LogP

0.4895

Topological Polar Surface Area

26.3 Å²

Hydrogen Bond Donor/Acceptor

0 / 2

Complexity

115

Safety Information

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GHS Hazard Pictograms

H226

H317

Hazard Statement

H226 Flammable liquid and vapor
Flammable liquids

H317 May cause an allergic skin reaction
Sensitization, Skin

Hazard Class

Class 3.2 Class 3.2

Synonyms & References

English

2-Methylenebutyrolactone
alpha-Methylene-gamma-butyrolactone
Dihydro-3-methylene-2(3H)-furanone
α-Methylene-γ-butyrolactone
alpha-Methylene-gamma-butyrolactone (stabilized with 2,6-Di-tert-butyl-p-cresol)
3-Methylenedihydro-2(3H)-furanone
3-methylideneoxolan-2-one
alpha-methylene gamma-butyrolactone
Methyl valerate
Tulipane
3-Methylenedihydro-2(3H)-furanone (stabilized with 2,6-Di-tert-butyl-p-cresol)
α-Methylene butyrolactone

MDL Number

MFCD00005407

Customs Code

29349990

FAQ

What are the physical and chemical properties of 3-Methylenedihydro-2(3H)-furanone (CAS: 547-65-9)?

3-Methylenedihydro-2(3H)-furanone is a colorless or white crystalline solid with a molecular weight of approximately 122.12 g/mol. It has a low solubility in water but is soluble in organic solvents such as ethanol. This compound is relatively stable under normal conditions but can react with strong bases or oxidizers. It is an important intermediate in various chemical syntheses.

How is 3-Methylenedihydro-2(3H)-furanone (CAS: 547-65-9) typically synthesized?

3-Methylenedihydro-2(3H)-furanone is typically synthesized via the Wittig reaction using methyl vinyl ketone and sodium bis(trimethylsilyl)amide (sodium bis(trimethylsilyl)amide). This method provides a high yield and good selectivity. Other routes include the reaction of furanone with methylene chloride in the presence of a suitable catalyst.

What industries use 3-Methylenedihydro-2(3H)-furanone (CAS: 547-65-9)?

3-Methylenedihydro-2(3H)-furanone is used in the pharmaceutical industry for the synthesis of certain drugs. It is also applied in the polymer industry as a monomer. Additionally, it plays a role in the development of sensors and semiconductors due to its unique chemical properties.

What precautions should be taken when handling 3-Methylenedihydro-2(3H)-furanone (CAS: 547-65-9)?

Proper personal protective equipment (PPE) such as gloves and goggles should be worn when handling 3-Methylenedihydro-2(3H)-furanone. It should be stored in a cool, dry place, away from oxidizers and strong bases. In case of spill, it should be handled in a fume hood, and appropriate safety data sheet (SDS) should be consulted for detailed handling instructions.