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139459

Sigma-Aldrich

Methyl crotonate

98%

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$32.00
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$86.50
500 ML
$133.00

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5 ML
$32.00
100 ML
$86.50
500 ML
$133.00

About This Item

Linear Formula:
CH3CH=CHCOOCH3
CAS Number:
623-43-8
Molecular Weight:
100.12
Beilstein/REAXYS Number:
1720292
EC Number:
210-793-7
MDL number:
MFCD00009287
UNSPSC Code:
12352100
PubChem Substance ID:
24848413
NACRES:
NA.22

$32.00

Only 3 left in stockDetails
Request a Bulk Order

Quality Level

100

assay

98%

form

liquid

refractive index

n20/D 1.423 (lit.)

bp

118-120 °C (lit.)

density

0.944 g/mL at 25 °C (lit.)

functional group

ester

SMILES string

COC(=O)\C=C\C

InChI

1S/C5H8O2/c1-3-4-5(6)7-2/h3-4H,1-2H3/b4-3+

InChI key

MCVVUJPXSBQTRZ-ONEGZZNKSA-N

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General description

Methyl crotonate undergoes vinylogous aldol reaction with enolizable aldehydes in the presence of aluminum tris(2,6-di-2-naphthylphenoxide)[1].

Application

Methyl crotonate was used to investigate chemoselectivity in the reaction between methyl crotonate and benzylamine catalyzed by lipase B from Candida antarctica using solvent engineering[2]. It was used as starting reagent during the total synthesis of phytotoxins solanapyrones D(1) and E(2)[3].

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

hcodes

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

30.2 °F - closed cup

flash_point_c

-1 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBK1679
STBH9090
STBG9199
STBG2664V
STBF0340V

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Hisahiro Hagiwara et al.
The Journal of organic chemistry, 67(17), 5969-5976 (2002-08-17)
The phytotoxins solanapyrones D (1) and E (2) have been synthesized from the decalone prepared by the domino Michael reaction of the kinetic enolate of optically pure acetylcyclohexene with methyl crotonate. The decalone was transformed into a solanapyrone core by
Jeffrey A Gazaille et al.
Organic letters, 14(11), 2678-2681 (2012-05-25)
The synthesis of the novel Lewis acid, aluminum tris(2,6-di-2-naphthylphenoxide) (ATNP), and its use in the vinylogous aldol reaction between methyl crotonate and enolizable aldehydes are described. ATNP is related to Yamamoto's Lewis acid, aluminum tris(2,6-diphenylphenoxide) (ATPH), but the 2-naphthyl groups
Solvent engineering: an effective tool to direct chemoselectivity in a lipase-catalyzed Michael addition.
Priego J, et al.
Tetrahedron, 65(2), 536-539 (2009)

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