3-methylideneoxolan-2-one

• ChemBase ID: 150925
• Molecular Formular: C5H6O2
• Molecular Mass: 98.09994
• Monoisotopic Mass: 98.03677943
• SMILES: C=C1CCOC1=O
• Canonical SMILES: C=C1CCOC1=O
• InChI: InChI=1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2
• InChIKey: GSLDEZOOOSBFGP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methylideneoxolan-2-one
• IUPAC Traditional name: tulipalin A
• Synonyms: Tulipane; alpha-Methylene-gamma-butyrolactone; 3-Methylenedihydro-2(3H)-furanone; α-Methylene-γ-butyrolactone; 2-甲烯基丁内酯; α-亚甲基-γ-丁内酯

Database IDs

• CAS Number: 547-65-9
• MDL Number: MFCD00005407
• Beilstein Number: 107939
• PubChem SID: 162245084; 24853566; 24884906
• PubChem CID: 68352

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.8341923
• LogD (pH = 7.4): 0.8341923
• Log P: 0.8341923
• Molar Refractivity: 24.686 cm^3
• Polarizability: 9.756357 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 86-88 °C/12 mmHg(lit.)
• Flash Point: 37 °C; 98.6 °F
• Density: 1.119 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.472; n20/D 1.472(lit.)

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 10-42/43
• Safety Statements: 23-36/37-45
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); 97%
• Grade: purum
• Contains: ~1% 2,6-di-tert-butyl-4-methylphenol as stabilizer; ~2% 2,6-di-tert-butyl-p-cresol as stabilizer
• Empirical Formula (Hill Notation): C5H6O2

DETAILS

Sigma Aldrich - 226416

Packaging
1, 5 g in glass bottle

Sigma Aldrich - 66735

Application
Very reactive Michael-acceptor; the α-methylene-γ-butyrolactone ring system exists in many natural products of biological interest