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Merck
CN

171859

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24850388
EC Number:
213-083-5
Beilstein/REAXYS Number:
605462
MDL number:
MFCD00008572

Key Documents

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Product Name

Methyl propiolate, 99%

InChI key

IMAKHNTVDGLIRY-UHFFFAOYSA-N

InChI

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

SMILES string

COC(=O)C#C

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

Quality Level

200

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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

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

60.8 °F - closed cup

flash_point_c

16 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCK6510
BCCG1929
BCCD0196
BCCB4031
BCBT5514

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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
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)
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