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MilliporeSigma

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
213-083-5
Beilstein/REAXYS Number:
605462
MDL number:
Assay:
99%
Form:
liquid

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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

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This Item
E46607419885110264
assay

99%

assay

99%

assay

98%

assay

≥99%

Quality Level

200

Quality Level

100

Quality Level

200

Quality Level

200

density

0.945 g/mL at 25 °C (lit.)

density

0.968 g/mL at 25 °C (lit.)

density

0.919 g/mL at 25 °C (lit.)

density

0.805 g/mL at 25 °C (lit.)

form

liquid

form

liquid

form

liquid

form

liquid

bp

103-105 °C (lit.)

bp

120 °C (lit.)

bp

52-53 °C/27 mmHg (lit.)

bp

80 °C (lit.)

refractive index

n20/D 1.408 (lit.)

refractive index

n20/D 1.412 (lit.)

refractive index

n20/D 1.418 (lit.)

refractive index

n20/D 1.379 (lit.)

Application

N-3 protecting reagent for uridines and thymidines.[1]
Methyl propiolate was used in the synthesis of polysubstituted 3-arylaminoacrylate and tetrahydropyrimidin-2-one derivatives[2]. It was also used as a thiol derivatizing agent for capillary electrophoresis[3].
Used in a one-pot, four-component synthesis of 1,2,3,5-benzenetetracarboxylates promoted by Ph3P.[4]

pictograms

FlameExclamation mark

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


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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)

Questions

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    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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