384267

Sigma-Aldrich

Methyl 3-butenoate

95%

Synonym(s):
Methyl vinylacetate
Linear Formula:
CH2=CHCH2COOCH3
CAS Number:
Molecular Weight:
100.12
Beilstein/REAXYS Number:
1741732
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

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.

Packaging

1, 5 g in ampule

Pictograms

Flame

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3272 3 / PGII

WGK Germany

WGK 3

Flash Point(F)

68.0 °F - closed cup

Flash Point(C)

20 °C - closed cup

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)....

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