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129712

Sigma-Aldrich

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:
14205-39-1
Molecular Weight:
115.13
Beilstein:
956592
EC Number:
238-056-5
MDL number:
MFCD00008072
UNSPSC Code:
12352100
PubChem Substance ID:
24847922
NACRES:
NA.22

Quality Level

200

Assay

97%

form

solid

mp

81-83 °C (lit.)

SMILES string

COC(=O)\C=C(\C)N

InChI

1S/C5H9NO2/c1-4(6)3-5(7)8-2/h3H,6H2,1-2H3/b4-3+

InChI key

XKORCTIIRYKLLG-ONEGZZNKSA-N

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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.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H317,H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

213.8 °F - closed cup

Flash Point(C)

101 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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