ethyl prop-2-ynoate

• ChemBase ID: 57995
• Molecular Formular: C5H6O2
• Molecular Mass: 98.09994
• Monoisotopic Mass: 98.03677943
• SMILES: C(#C)C(=O)OCC
• Canonical SMILES: CCOC(=O)C#C
• InChI: InChI=1S/C5H6O2/c1-3-5(6)7-4-2/h1H,4H2,2H3
• InChIKey: FMVJYQGSRWVMQV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl prop-2-ynoate
• IUPAC Traditional name: ethyl propiolate
• Synonyms: Ethyl propiolate; Ethyl acetylenecarboxylate; Ethyl propiolate; Ethyl propiolate; Ethyl prop-2-ynoate; Propiolic acid ethyl ester; 乙炔基羧酸乙酯; 丙炔酸乙酯

Database IDs

• CAS Number: 623-47-2
• EC Number: 210-795-8
• MDL Number: MFCD00009184
• Beilstein Number: 878250
• PubChem SID: 162062758; 24894572; 24887914
• PubChem CID: 12182

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.91800505
• LogD (pH = 7.4): 0.91800505
• Log P: 0.91800505
• Molar Refractivity: 25.3017 cm^3
• Polarizability: 9.635451 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 9°C; 9°C
• Boiling Point: 118-120°C; 118-120°C; 120 °C(lit.); 120°C
• Flash Point: 23°C; 23°C(73°F); 25 °C; 77 °F
• Density: 0.963; 0.968 g/ml; 0.968 g/mL at 25 °C(lit.)
• Refractive Index: 1.4120; n20/D 1.412(lit.); n20/D 1.413

Safety Information

• Storage Warning: Flammable/Toxic/Harmful/Lachrymatory/Keep Cold; KEEP COLD, LACHRYMATOR, TOXIC, FLAMMABLE
• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 3272; UN3272
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-36/37/38; R:10-36/37/38
• Safety Statements: 26-36; 26-37-60; S:16-20-25-26-37/39
• TSCA Listed: false; 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3272 3/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (GC); 97%; 98%; 99%
• Grade: purum
• Impurities: ≤0.1% DCADMA; ≤0.2% dichloromethane
• Linear Formula: HC≡CCO2C2H5

DETAILS

MP Biomedicals - 05205878

MP Biomedicals Rare Chemical collection

Sigma Aldrich - E46607

Application
Halogenated derivatives were used as substrates for direct, asymmetric alkynylation of cyclic β-ketoesters using chiral phase-transfer catalysts.1 Also employed in a one-pot , four-component synthesis of benzene-1,2,3,5-tetracarboxylates promoted by Ph3P.2
Packaging
5, 25, 100 g in glass bottle

Sigma Aldrich - 81869

Other Notes
Synthesis of ethyl (Z)-2,3-dibromoacrylate1

REFERENCES

• Regio- and stereospecific hydrohalogenation of propiolic acid derivatives is illustrated by the conversion of ethyl propiolate to (Z)-3-bromo-2-propenoate in the presence of LiBr + acetic acid in acetonitrile: J. Org. Chem., 57, 709 (1992); Org. Synth. Coll., 9, 412 (1998).
• n-BuLi gives the alkynyllithium derivative, stable at low temperatures: J. Org. Chem., 45, 28 (1980). For use in a sequence for the synthesis of butenolides, see: J. Am. Chem. Soc., 101, 1544 (1979):
  
• Conjugate addition of allylic alcohols in the presence of trimethylamine proceeds via an intermediate betaine and leads to allyl vinyl ethers which undergo the Claisen rearrangement to give δ-unsaturated aldehydes: J. Org. Chem., 48, 5406 (1983); Org. Synth. Coll., 8, 536 (1993):