(3E)-4-methoxybut-3-en-2-one

• ChemBase ID: 148139
• Molecular Formular: C5H8O2
• Molecular Mass: 100.11582
• Monoisotopic Mass: 100.0524295
• SMILES: CC(=O)/C=C/OC
• Canonical SMILES: CO/C=C/C(=O)C
• InChI: InChI=1S/C5H8O2/c1-5(6)3-4-7-2/h3-4H,1-2H3/b4-3+
• InChIKey: VLLHEPHWWIDUSS-ONEGZZNKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3E)-4-methoxybut-3-en-2-one
• IUPAC Traditional name: (3E)-4-methoxybut-3-en-2-one
• Synonyms: trans-4-Methoxy-3-buten-2-one; 4-Methoxy-3-buten-2-one; 反式-4-甲氧基-3-丁烯-2-酮; 4-甲氧基-3-丁烯-2-酮

Database IDs

• CAS Number: 51731-17-0; 4652-27-1
• EC Number: 257-364-0; 225-087-4
• MDL Number: MFCD00008778
• Beilstein Number: 1741053; 2070991
• PubChem SID: 162242316; 24847477; 24883646
• PubChem CID: 639675

CALCULATED PROPERTIES

• Acid pKa: 19.389936
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.38498774
• LogD (pH = 7.4): 0.38498774
• Log P: 0.38498774
• Molar Refractivity: 27.5714 cm^3
• Polarizability: 10.472008 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 200 °C(lit.); 66-69°C/12mm
• Flash Point: 145.4 °F; 63 °C; 63°C(145°F)
• Density: 0.982 g/mL at 25 °C(lit.); 0.990
• Refractive Index: 1.4650; n20/D 1.468(lit.); n20/D 1.469

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• GHS Hazard statements: H227
• GHS Precautionary statements: P210-P280-P370+P378A-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, 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); 90%; tech. 90%
• Grade: purum; technical grade
• Linear Formula: CH3OCH=CHCOCH3

DETAILS

Sigma Aldrich - 122068

Packaging
10, 50, 250 g in glass bottle

Sigma Aldrich - 64935

Other Notes
Intermediate; starting material for the preparation of 1-methoxy-3-trimethylsiloxy-1,3-butadiene1,2; Preparation of γ-pyranones3,4

REFERENCES

• Arylation of the lithio-derivative provides a route to 2-aryl--pyrones: Tetrahedron Lett., 21, 1197, 2773 (1980):