All Photos(1)

171859

Sigma-Aldrich

Methyl propiolate

99%

Synonym(s):
Methyl acetylenecarboxylate
Linear Formula:
HC≡CCO2CH3
CAS Number:
Molecular Weight:
84.07
Beilstein:
605462
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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.)

SMILES string

COC(=O)C#C

InChI

1S/C4H4O2/c1-3-4(5)6-2/h1H,2H3

InChI key

IMAKHNTVDGLIRY-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

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.

Packaging

2.5, 10, 50 g in glass bottle

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard 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

Certificate of Analysis

Certificate of Origin

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
Tetrahedron Letters, 36, 3261-3261 (1995)
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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service