4-methylideneoxetan-2-one

• ChemBase ID: 127055
• Molecular Formular: C4H4O2
• Molecular Mass: 84.07336
• Monoisotopic Mass: 84.02112937
• SMILES: O=C1OC(=C)C1
• Canonical SMILES: C=C1CC(=O)O1
• InChI: InChI=1S/C4H4O2/c1-3-2-4(5)6-3/h1-2H2
• InChIKey: WASQWSOJHCZDFK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methylideneoxetan-2-one
• IUPAC Traditional name: diketene
• Synonyms: γ-methylenebutyrolactone; Diketene; Diketene; 双乙烯酮

Database IDs

• CAS Number: 674-82-8
• EC Number: 211-617-1
• MDL Number: MFCD00005173
• Beilstein Number: 104541
• PubChem SID: 24866429; 162221378
• PubChem CID: 12661
• Chemspider ID: 12140
• Wikipedia Title: Diketene

CALCULATED PROPERTIES

• Acid pKa: 19.771315
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.08109592
• LogD (pH = 7.4): 0.08109592
• Log P: 0.08109592
• Molar Refractivity: 20.3158 cm^3
• Polarizability: 7.930509 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -7 °C
• Boiling Point: 127 °C; 69-70 °C/100 mmHg(lit.)
• Flash Point: 34 °C; 93.2 °F
• Auto Ignition Point: 590 °F
• Density: 1.09 g cm^-3; 1.09 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.439(lit.)
• Vapor Pressure: 7.9 mmHg ( 20 °C)
• Vapor Density: 2.9 (vs air)

Safety Information

• RTECS: RQ8225000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2521
• German water hazard class: 1
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 10-20
• Safety Statements: 3
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H332
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2521 6.1/PG 1

Product Information

• Contains: copper sulfate as stabilizer
• Empirical Formula (Hill Notation): C4H4O2

DETAILS

Sigma Aldrich - 422363

Application
Employed in the convenient preparation of acetoacetic acid derivatives and heterocycles.1
Packaging
100 mL in Sure/Seal™
5 mL in ampule