171859
Methyl propiolate
99%
Synonym(s):
Methyl acetylenecarboxylate
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About This Item
Linear Formula:
HC≡CCO2CH3
CAS Number:
Molecular Weight:
84.07
Beilstein:
605462
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
99%
form
liquid
refractive index
n20/D 1.408 (lit.)
bp
103-105 °C (lit.)
density
0.945 g/mL at 25 °C (lit.)
functional group
ester
SMILES string
COC(=O)C#C
InChI
1S/C4H4O2/c1-3-4(5)6-2/h1H,2H3
InChI key
IMAKHNTVDGLIRY-UHFFFAOYSA-N
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Application
N-3 protecting reagent for uridines and thymidines.
Methyl propiolate was used in the synthesis of polysubstituted 3-arylaminoacrylate and tetrahydropyrimidin-2-one derivatives. It was also used as a thiol derivatizing agent for capillary electrophoresis.
Used in a one-pot, four-component synthesis of 1,2,3,5-benzenetetracarboxylates promoted by Ph3P.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
60.8 °F - closed cup
Flash Point(C)
16 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Li-Li Zhang et al.
Molecular diversity, 18(1), 79-89 (2014-01-31)
Polysubstituted 3-arylaminoacrylate and tetrahydropyrimidin-2-one derivatives could be selectively produced from the one-pot domino reaction of arylamines, methyl propiolate, aromatic aldehydes, and urea in ethanol in the presence of FeCl3 as catalyst. Under similar reactions secondary amines such as morpholine and
Eirini-Chrysanthi Tsardaka et al.
Journal of chromatography. A, 1300, 204-208 (2013-06-04)
In this study we demonstrate - for the first time - the suitability of methyl propiolate - an alkylester of propiolic acid - as a thiol derivatizing reagent for capillary electrophoresis. Glutathione (as analyte in yeast samples) and N-acetylcysteine (as
Graziella Tocco et al.
Journal of agricultural and food chemistry, 68(40), 11088-11095 (2020-09-15)
The present study reports on the powerful nematicidal activity of a series of electron-deficient alkynes against the root-knot nematode Meloidogyne incognita (Kofoid and White) Chitwood. Interestingly, we found that the conjugation of electron-withdrawing carbonyl groups to an alkyne triple bond
Helvetica Chimica Acta, 89, 2918-2918 (2006)
Tetrahedron Letters, 36, 3261-3261 (1995)
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