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317519 Sigma-Aldrich

Methyl 2-acetamidoacrylate

98%

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Properties

Related Categories Acrylate, Acrylic Monomers, Building Blocks, C6 to C7, Carbonyl Compounds,
Quality Level   100
assay   98%
bp   104 °C/8 mmHg (lit.)
mp   50-52 °C (lit.)
SMILES string   COC(=O)C(=C)NC(C)=O
InChI   1S/C6H9NO3/c1-4(6(9)10-3)7-5(2)8/h1H2,2-3H3,(H,7,8)
InChI key   SMWNFFKPVLVOQQ-UHFFFAOYSA-N

Description

General description

Conjugated addition of secondary amines, imidazole and pyrazole to methyl 2 methyl 2-acetamidoacrylate in the presence of a catalyst results in the formation of β-Dialkylamino-α-alanine and β-(N-heteroaryl)-α-alanine derivatives. Methyl-2-acetamidoacrylate (M2AA) is an anti-inflammatory agent. The catalytic reaction of methyl 2-acetamidoacrylate with Grignard’s reagents affords α-amino esters. M2AA can form thermosensitive copolymers with methyl acrylate.

Methyl ester of 2-acetamidoacrylate . methyl 2-acetamidoacrylate (Me-2-AA) is a di-unsaturated α-amino acid derivative. methyl-2-acetamidoacrylate exihibits anti -inflammatory properties, it is very effective against lipopolysaccharide (LPS)- induced nitric oxide production by RAW 264.

Application

Methyl 2-acetamidoacrylate can undergo [2+2] cycloaddition (Michael–Dieckmann-type reaction) with ketene diethyl acetal to yield the cyclobutane core. It may be used in rhodium-catalyzed 2-alkenylpyrrole formation.

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
235.4 °F - closed cup
Flash Point(C) 
113 °C - closed cup
Protocols & Articles
Peer-Reviewed Papers
15

References

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