129712
Methyl 3-aminocrotonate
97%
Synonym(s):
Methyl 3-amino-2-butenoate
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About This Item
Linear Formula:
CH3C(NH2)=CHCOOCH3
CAS Number:
Molecular Weight:
115.13
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
238-056-5
Beilstein/REAXYS Number:
956592
MDL number:
Assay:
97%
Form:
solid
InChI key
XKORCTIIRYKLLG-ONEGZZNKSA-N
InChI
1S/C5H9NO2/c1-4(6)3-5(7)8-2/h3H,6H2,1-2H3/b4-3+
SMILES string
COC(=O)\C=C(\C)N
assay
97%
form
solid
mp
81-83 °C (lit.)
functional group
amine, ester
Quality Level
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General description
Methyl 3-aminocrotonate undergoes waste-free solid-state cascade reaction with crystalline ninhydrin.
Application
Methyl 3-aminocrotonate (Methyl 3-amino-2-butenoate) was used to synthesize 4-aryl-1,4-dihydropyridines possessing potential calcium channel blocking activity.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1 - Skin Sens. 1
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
213.8 °F - closed cup
flash_point_c
101 °C - closed cup
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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Gerd Kaupp et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 8(3), 594-600 (2002-02-22)
Crystalline ninhydrin (1) undergoes waste-free solid-state cascade reactions with dimedone, L-proline, three o-phenylenediamines, o-mercaptoaniline, two ureas, three thioureas, and methyl 3-aminocrotonate. The yields are quantitative and give pure crystalline products without workup just by milling stoichiometric mixtures of the crystalline
P Jain et al.
Die Pharmazie, 61(5), 400-405 (2006-05-27)
Synthesis of a new series of 4-aryl-1,4-dihydropyridines possessing potential calcium channel blocking activity along with good vasodilatory profile is reported. The compounds were synthesized using modified Hantzsch condensation of various aldehydes with methyl 3-aminocrotonate in the presence of a catalytic
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