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49661

Sigma-Aldrich

Methyl 4-pentenoate

≥95.0% (GC)

Synonym(s):

4-Pentenoic acid methyl ester, Allylacetic acid methyl ester, Methyl allylacetate

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About This Item

Empirical Formula (Hill Notation):
C6H10O2
CAS Number:
818-57-5
Molecular Weight:
114.14
MDL number:
MFCD03990590
UNSPSC Code:
12352100
PubChem Substance ID:
57651216
NACRES:
NA.22

Assay

≥95.0% (GC)

refractive index

n20/D 1.415
n20/D 1.415

SMILES string

COC(=O)CCC=C

InChI

1S/C6H10O2/c1-3-4-5-6(7)8-2/h3H,1,4-5H2,2H3

InChI key

SHCSFZHSNSGTOP-UHFFFAOYSA-N

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General description

Methyl 4-pentenoate is an unsaturated methyl ester that is prepared by the esterification of 1-pentenoic acid with methanol. It undergoes amidation with formamide via acetone-initiated photochemical reaction to form a 1:1 adduct. The metathesis of methyl 4-pentenoate with different Mo(VI)alkylidene complexes have been reported. It acts as a chain transfer agent during the polymerization of exo,exo-5,6-bis(methoxymethyl)-7-oxabicyclo[2.2.1]hept-2-ene using RuII(H20)6(tos)2 (tos =p-toluenesulfonate) as a catalyst.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H319

Precautionary Statements

P210 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

84.2 °F - closed cup

Flash Point(C)

29 °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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The Light-Induced Amidation of Terminal Olefins1.
Elad D and Rokach J.
The Journal of Organic Chemistry, 29(7), 1855-1859 (1964)
Chain transfer during the aqueous ring-opening metathesis polymerization of 7-oxanorbornene derivatives.
France MB, et al.
Macromolecules, 26(18), 4742-4747 (1993)
Coupling of terminal olefins by molybdenum (VI) imido alkylidene complexes.
Fox HH, et al.
Organometallics, 13(2), 635-639 (1994)
Majd Al-Naji et al.
ChemSusChem, 12(12), 2628-2636 (2019-04-18)
The need for more sustainable products and processes has led to the use of new methodologies with low carbon footprints. In this work, an efficient tandem process is demonstrated for the liquid-phase catalytic upgrading of lignocellulosic biomass-derived γ-valerolactone (GVL) with

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