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MilliporeSigma

384267

Methyl 3-butenoate

95%

Synonym(s):

Methyl vinylacetate

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$357.00

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About This Item

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

Key Documents

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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.)

functional group

allyl
ester

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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1 of 4

This Item
407429343587425117
Methyl 3-butenoate 95%

Sigma-Aldrich

384267

Methyl 3-butenoate

Methyl 3-methoxypropionate ≥99%

Sigma-Aldrich

407429

Methyl 3-methoxypropionate

Methyl 4,4-dimethoxy-3-oxovalerate 97%

Sigma-Aldrich

343587

Methyl 4,4-dimethoxy-3-oxovalerate

Ethyl 2-butynoate 98%

Sigma-Aldrich

425117

Ethyl 2-butynoate

assay

95%

assay

≥99%

assay

97%

assay

98%

Quality Level

100

Quality Level

200

Quality Level

-

Quality Level

200

density

0.939 g/mL at 25 °C (lit.)

density

1.009 g/mL at 25 °C (lit.)

density

1.111 g/mL at 25 °C (lit.)

density

0.962 g/mL at 25 °C (lit.)

refractive index

n20/D 1.409 (lit.)

refractive index

n20/D 1.402 (lit.)

refractive index

n20/D 1.435 (lit.)

refractive index

n20/D 1.436 (lit.)

bp

112 °C (lit.)

bp

142-143 °C (lit.)

bp

69-73 °C/0.35 mmHg (lit.)

bp

160-161 °C/730 mmHg (lit.)

form

liquid

form

liquid

form

liquid

form

liquid

General description

Methyl 3-butenoate is an olefin ester. It is reported to undergo Iron carbonyl-promoted isomerization to afford α, β-unsaturated esters.[1] It is one of the reaction products formed during flash vacuum thermolysis of (−)-cocaine.[2] The H2 and CH4 chemical ionization mass spectra of methyl 3-butenoate has been reported.[3]

Application

Methyl 3-butenoate may be employed for the synthesis of dipeptide olefin isosteres using intermolecular olefin cross-metathesis.[4]

accessory

Product No.
Description
Pricing

pictograms

Flame
GHS02

signalword

Danger

hcodes

H225

pcodes

P210

Hazard Classifications

Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

68.0 °F - closed cup

flash_point_c

20 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKBT0072V
MKBG3376V
23298MJ
15124KH
09930KN

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The flash vacuum thermolysis of (-)-cocaine.
Sisti NJ, et al.
Tetrahedron Letters, 30(44), 5977-5980 (1989)
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)
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
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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