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171859

Sigma-Aldrich

Methyl propiolate

99%

Synonym(s):

Methyl acetylenecarboxylate

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About This Item

Linear Formula:
HC≡CCO2CH3
CAS Number:
922-67-8
Molecular Weight:
84.07
Beilstein:
605462
EC Number:
213-083-5
MDL number:
MFCD00008572
UNSPSC Code:
12352100
PubChem Substance ID:
24850388
NACRES:
NA.22

Quality Level

200

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

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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.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H315,H319,H335

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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)
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