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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
form:
solid
Assay:
97%

Quality Level

200

Assay

97%

form

solid

mp

81-83 °C (lit.)

functional group

amine
ester

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

129712-5G:
129712-VAR:
129712-500G:
129712-100G:
129712-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
STBH6667
STBB1828V
S87968
S85243
STBB1828

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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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