139459
Methyl crotonate
98%
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About This Item
Linear Formula:
CH3CH=CHCOOCH3
CAS Number:
Molecular Weight:
100.12
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
210-793-7
Beilstein/REAXYS Number:
1720292
MDL number:
Product Name
Methyl crotonate, 98%
InChI key
MCVVUJPXSBQTRZ-ONEGZZNKSA-N
InChI
1S/C5H8O2/c1-3-4-5(6)7-2/h3-4H,1-2H3/b4-3+
SMILES string
COC(=O)\C=C\C
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
Quality Level
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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. It was used as starting reagent during the total synthesis of phytotoxins solanapyrones D(1) and E(2).
General description
Methyl crotonate undergoes vinylogous aldol reaction with enolizable aldehydes in the presence of aluminum tris(2,6-di-2-naphthylphenoxide).
signalword
Danger
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 2
Storage Class
3 - Flammable liquids
wgk
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
Regulatory Information
危险化学品
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Solvent engineering: an effective tool to direct chemoselectivity in a lipase-catalyzed Michael addition.
Priego J, et al.
Tetrahedron, 65(2), 536-539 (2009)
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
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
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