Methyl 3-aminocrotonate Chemical Properties

Melting point:

81-83 °C(lit.)

Boiling point:

112°C 42mm

Density 

1.1808 (rough estimate)

vapor pressure 

2.79-2.853hPa at 25℃

refractive index 

1.4538 (estimate)

Flash point:

91 °C

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

18g/l

form 

Crystalline Powder

pka

5.27±0.70(Predicted)

color 

White to slightly yellow

PH

8-9 (18g/l, H2O, 20℃)

Water Solubility 

insoluble

Sensitive 

Hygroscopic

BRN 

956592

InChIKey

XKORCTIIRYKLLG-ONEGZZNKSA-N

LogP

-0.27 at 25℃

CAS DataBase Reference

14205-39-1(CAS DataBase Reference)

EPA Substance Registry System

2-Butenoic acid, 3-amino-, methyl ester (14205-39-1)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

37/39-26-24/25

WGK Germany 

3

RTECS 

EM9092500

TSCA 

Yes

HS Code 

29224995

MSDS

• Language:English Provider:Methyl 3-aminocrotonate
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Methyl 3-aminocrotonate Usage And Synthesis

Chemical Properties

Crystals, yellowish-white

Uses

Methyl 3-aminocrotonate is used as intermediate for the syntheses of pharmaceuticals (e.g. 1,4-dihydropyridine derivatives) as well as for the manufacture of stabilizers and plastics. Product Data Sheet

Uses

Methyl 3-aminocrotonate (Methyl 3-amino-2-butenoate) was used to synthesize 4-aryl-1,4-dihydropyridines possessing potential calcium channel blocking activity.

Uses

Nitrendipine (N490150) metabolite. The pharmacokinetics of Nitrendipine was studied in the rat and 6 major metabolites were identified.

Application

Methyl 3-aminocrotonate reacts with benzene to form the corresponding E-2-phenyliodonio tosylate in good yield. This new alkenyl iodonium salt upon reaction with various nucleophiles offers an easy access to substituted enamine derivatives of crotonic acid. The reaction can be also extended to N-substituted crotonates^[1].

Preparation

3-Aminocrotonate Esters, e.g., methyl 3- aminocrotonate [14205-39-1] (3-amino-2-butenoic acid, methyl ester) can be prepared by treatment of acetoacetates with aqueous ammonia. They are mainly used in the production of a series of the dihydropyridine-type calcium antagonists.

General Description

Methyl 3-aminocrotonate undergoes waste-free solid-state cascade reaction with crystalline ninhydrin.

Flammability and Explosibility

Not classified

References

[1] IOANNIS PAPOUTSIS; Anastasios V ?; Spyros Spyroudis ?. Reactivity of a new alkenyl phenyliodonium tosylate derived from methyl 3-aminocrotonate[J]. Tetrahedron, 1998. DOI:10.1016/S0040-4020(97)10354-4.

Methyl 3-aminocrotonate(14205-39-1)Related Product Information

• FATTY ACID METHYL ESTER MIX C8-C22
• 4-Morpholineethanesulfonic acid
• METSULFURON METHYL
• Methyl 2-(methylamino)benzoate
• Methyl carbamate
• METHYL 4-(4-AMINOPHENYL)BUTANOATE
• Methyl salicylate
• Methyl anthranilate
• Methyl acetate
• Thiophanate-methyl
• Pirimiphos-methyl
• Tribenuron methyl
• Crotonic acid
• Methyl cinnamate
• Kresoxim-methyl
• trans-Methyl crotonate
• Methyl 4-aminobenzoate
• Methyl 4-bromocrotonate