| Identification | More | [Name]
Ethyl propiolate | [CAS]
623-47-2 | [Synonyms]
ACETYLENECARBOXYLIC ACID ETHYL ESTER
EPL
ETHYL ACETYLENECARBOXYLATE
ETHYL PROPIOLATE
PROPARGYLIC ACID ETHYL ESTER
PROPIOLIC ACID ETHYL ESTER
(Ethoxycarbonyl)acetylene
2-Propynoic acid, ethyl ester
Ethyl 2-propynoate
Ethyl propynoate
Ethyl propiolate, (Ethyl acetylenecarboxylate
Ethyl acetylenecarboxylate~Propiolic acid ethyl ester~Propynoic acid ethyl ester
Ethylpropiolate,99%
prop-2-ynoic acid ethyl ester
Carboethoxyacetylene
Ethyl acetylenemonocarboxylate
Ethyl propargylate
Ethyl propiolate ,98% | [EINECS(EC#)]
210-795-8 | [Molecular Formula]
C5H6O2 | [MDL Number]
MFCD00009184 | [Molecular Weight]
98.1 | [MOL File]
623-47-2.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to pale yellow liquid | [Melting point ]
9°C | [Boiling point ]
120 °C (lit.) | [density ]
0.968 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.412(lit.)
| [Fp ]
74 °F
| [storage temp. ]
2-8°C
| [solubility ]
Miscible with alcohol. | [form ]
Liquid | [color ]
Clear colorless to pale yellow | [Specific Gravity]
0.968 | [Water Solubility ]
miscible | [Detection Methods]
GC,NMR | [Merck ]
3846 | [BRN ]
878250 | [Dielectric constant]
7.0 | [CAS DataBase Reference]
623-47-2(CAS DataBase Reference) | [NIST Chemistry Reference]
Ethyl propiolate(623-47-2) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,F | [Risk Statements ]
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin .
R36:Irritating to the eyes.
R11:Highly Flammable. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection .
S16:Keep away from sources of ignition-No smoking .
S33:Take precautionary measures against static discharges .
S29:Do not empty into drains .
S24:Avoid contact with skin .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) . | [RIDADR ]
UN 3272 3/PG 3
| [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29161980 |
| Hazard Information | Back Directory | [Hazard]
Flammable; lachrymator. | [Chemical Properties]
clear colorless to pale yellow liquid | [Uses]
(Ethyl propiolate)Halogenated derivatives were used as substrates for direct, asymmetric alkynylation of cyclic ß-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
| [Uses]
In organic synthesis; peptide coupling reagent. | [Definition]
ChEBI: The ethyl ester of prop-2-ynoic acid. | [Synthesis]
The general procedure for the synthesis of ethyl propargylate from ethanol and propargylate was as follows: propargylate (310 μL, 5 mmol; Alfa Aesar, Ward Hill, MA; Catalog No. A13245) was dissolved in 13 mL of ethanol to form a colorless solution, followed by the slow addition of concentrated sulfuric acid (139 μL, 2.5 mmol) to this solution. The reaction mixture was heated to reflux for 24 hours. Upon completion of the reaction, the reaction was quenched with 13 mL of water followed by extraction with dichloromethane (10 mL; three times). The organic phases were combined, washed sequentially with water (10 mL; three times) and brine (10 mL), and then dried with anhydrous Na2SO4 (Thermo Fisher Scientific, Pittsburgh, PA; catalog number S421-3). The solvent was removed by distillation under reduced pressure to give the light yellow oily product ethyl propiolate (177 mg, 36% yield). The product was characterized by 1H NMR (400 MHz, CDCl3, δ): 4.26 (q, 3JH-H = 7.1 Hz, CH2, 2H), 2.92 (s, C≡CH, 1H), 1.33 (t, 3JH-H = 7.2 Hz, CH3, 3H). | [References]
[1] Journal of the American Chemical Society, 1988, vol. 110, p. 3965
[2] Patent: US2016/264506, 2016, A1. Location in patent: Paragraph 0035
[3] Chemische Berichte, 1926, vol. 59, p. 1689
[4] Nippon Kagaku Zasshi, 1956, vol. 77, p. 1689,1691
[5] Chem.Abstr., 1959, p. 5163 |
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