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384267

Sigma-Aldrich

Methyl 3-butenoate

95%

Synonym(s):

Methyl vinylacetate

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About This Item

Linear Formula:
CH2=CHCH2COOCH3
CAS Number:
3724-55-8
Molecular Weight:
100.12
Beilstein:
1741732
EC Number:
223-076-9
MDL number:
MFCD00082587
UNSPSC Code:
12352100
PubChem Substance ID:
24863656
NACRES:
NA.22

Quality Level

100

Assay

95%

form

liquid

refractive index

n20/D 1.409 (lit.)

bp

112 °C (lit.)

density

0.939 g/mL at 25 °C (lit.)

SMILES string

COC(=O)CC=C

InChI

1S/C5H8O2/c1-3-4-5(6)7-2/h3H,1,4H2,2H3

InChI key

GITITJADGZYSRL-UHFFFAOYSA-N

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General description

Methyl 3-butenoate is an olefin ester. It is reported to undergo Iron carbonyl-promoted isomerization to afford α, β-unsaturated esters. It is one of the reaction products formed during flash vacuum thermolysis of (−)-cocaine. The H2 and CH4 chemical ionization mass spectra of methyl 3-butenoate has been reported.

Application

Methyl 3-butenoate may be employed for the synthesis of dipeptide olefin isosteres using intermolecular olefin cross-metathesis.

accessory

Product No.
Description
Pricing

Pictograms

Flame
GHS02

Signal Word

Danger

Hazard Statements

H225

Precautionary Statements

P210

Hazard Classifications

Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

68.0 °F - closed cup

Flash Point(C)

20 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Site of protonation in the chemical ionization mass spectra of olefinic methyl esters.
Harrison AX and Ichikawa H.
Org. Mass Spectrom., 15(5), 244-248 (1980)
The flash vacuum thermolysis of (-)-cocaine.
Sisti NJ, et al.
Tetrahedron Letters, 30(44), 5977-5980 (1989)
Kuo-Chen Shih et al.
The Journal of organic chemistry, 61(22), 7784-7792 (1996-11-01)
Ultraviolet photolysis of stoichiometric amounts of methyl oleate and Fe(CO)(5) in hexanes solvent at 0 degrees C gives Fe(CO)(3)(eta(4)-alpha,beta-ester) in which the alpha,beta-unsaturated ester isomer of methyl oleate is stabilized by eta(4)-oxadiene pi coordination of the olefin and ester carbonyl
Melissa M Vasbinder et al.
The Journal of organic chemistry, 67(17), 6240-6242 (2002-08-17)
An approach to the synthesis of dipeptide olefin isosteres using intermolecular olefin cross-metathesis is presented. In particular, a synthesis of the Pro-Gly isostere (1) is reported. Conversion of N-BOC-proline into the corresponding vinyl-substituted carbamate provides the N-terminal cross-metathesis partner (2).
Rachel Chapla et al.
Polymers, 12(12) (2020-12-20)
Local mechanical stiffness influences cell behavior, and thus cell culture scaffolds should approximate the stiffness of the tissue type from which the cells are derived. In synthetic hydrogels, this has been difficult to achieve for very soft tissues such as

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