ethyl 3-ethoxyprop-2-enoate

• ChemBase ID: 74059
• Molecular Formular: C7H12O3
• Molecular Mass: 144.16838
• Monoisotopic Mass: 144.07864424
• SMILES: O(CC)/C=C/C(=O)OCC
• Canonical SMILES: CCO/C=C/C(=O)OCC
• InChI: InChI=1S/C7H12O3/c1-3-9-6-5-7(8)10-4-2/h5-6H,3-4H2,1-2H3
• InChIKey: ITQFPVUDTFABDH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 3-ethoxyprop-2-enoate; ethyl (2E)-3-ethoxyprop-2-enoate
• IUPAC Traditional name: ethyl 3-ethoxy-2-propenoate
• Synonyms: 3-Ethoxy-2-propenoic Acid Ethyl Ester; Ethyl 3-Ethoxyacrylate; Ethyl β-Ethoxyacrylate; NSC 6828; 3-Ethoxyacrylic Acid Ethyl Ester(cis/trans-Mixture); 3-Ethoxy-(E)-2-propenoic acid ethyl ester; 3-Ethoxyacrylic acid ethyl ester; Ethyl trans-3-ethoxyacrylate; Ethyl 3-ethoxy-2-propenoate; Ethyl 3-ethoxyacrylate; Ethyl 3-ethoxyacrylate; Ethyl 3-ethoxy-2-propenoate; (E)-Ethyl 3-ethoxyacrylate; 反式 3-乙氧基丙烯酸乙酯; 3-乙氧基-2-丙烯酸乙酯; 3-乙氧基丙烯酸乙酯

Database IDs

• CAS Number: 5941-55-9; 1001-26-9
• EC Number: 000-000-0
• MDL Number: MFCD00009863
• Beilstein Number: 1721612
• PubChem SID: 24855037; 162038978
• PubChem CID: 5366269

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.1482055
• LogD (pH = 7.4): 1.1482055
• Log P: 1.1482055
• Molar Refractivity: 38.2866 cm^3
• Polarizability: 14.862389 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -34°C
• Boiling Point: 191-192°C; 195-196 °C(lit.); 195-196°C
• Flash Point: 168.8 °F; 76 °C; 80°C(176°F)
• Density: 0.991; 0.998 g/mL at 25 °C(lit.)
• Refractive Index: 1.4460; n20/D 1.446(lit.)

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 36/38
• Safety Statements: 26; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H227-H303-H313; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280G-P305+P351+P338
• 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: 95+%; 97%; 98%
• Linear Formula: CH3CH2OCH=CHCOOCH2CH3

DETAILS

Sigma Aldrich - 250120

Packaging
1, 5, 50 g in glass bottle

Toronto Research Chemicals - E890900

Used in the preparation of N-[3-(3-Cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl]-N-ethylacetamide, a principal impurity of Zaleplon (Z145000).

REFERENCES

• Doplet, M., et al.: Drugs, 60, 413 (2000)
• Bharathi, C., et al.: J. Pharm. Biomed. Anal., 77, 101 (2000)
• Jagusch, C., et al.: Bioorg. Med. Chem., 16, 1992 (2000)
• Malonic aldehyde-ester equivalent. Reacts with ortho esters in the presence of ammonia to give good yields of pyrimidinones. With ammonia alone, the 2-pyridone-5-carboxylate could be obtained: Synthesis, 286 (1974):