methyl (2E)-4-oxopent-2-enoate

• ChemBase ID: 152213
• Molecular Formular: C6H8O3
• Molecular Mass: 128.12592
• Monoisotopic Mass: 128.04734412
• SMILES: CC(=O)/C=C/C(=O)OC
• Canonical SMILES: COC(=O)/C=C/C(=O)C
• InChI: InChI=1S/C6H8O3/c1-5(7)3-4-6(8)9-2/h3-4H,1-2H3/b4-3+
• InChIKey: GLVNZYODMKSEPS-ONEGZZNKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2E)-4-oxopent-2-enoate
• IUPAC Traditional name: methyl (2E)-4-oxopent-2-enoate
• Synonyms: Methyl trans-β-acetylacrylate; Methyl trans-4-oxo-2-pentenoate; 反-β-乙酰基丙烯酸甲酯; 反-4-氧-2-戊烯酸甲酯

Database IDs

• CAS Number: 2833-24-1
• MDL Number: MFCD00059331
• Beilstein Number: 906914
• PubChem SID: 162246358; 24886900
• PubChem CID: 5363720

CALCULATED PROPERTIES

• Acid pKa: 19.401012
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.6679386
• LogD (pH = 7.4): 0.6679386
• Log P: 0.6679386
• Molar Refractivity: 32.9272 cm^3
• Polarizability: 12.425715 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 59-61 °C; 59-61 °C(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC)
• Linear Formula: CH3COCH=CHCO2CH3

DETAILS

Sigma Aldrich - 75944

Other Notes
Reactive enone; conjugate addition of ketones and similar compounds, e.g. for Robinson annelations1,2; DA-cycloadditions3,4
Packaging
1, 5 g in glass bottle