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317519

Methyl 2-acetamidoacrylate

98%

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About This Item

Linear Formula:
H2C=C(NHCOCH3)CO2CH3
CAS Number:
35356-70-8
Molecular Weight:
143.14
NACRES:
NA.23
PubChem Substance ID:
24859082
UNSPSC Code:
12162002
MDL number:
MFCD00013394
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Quality Segment

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

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Codes

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

235.4 °F - closed cup

Flash Point (°C)

113 °C - closed cup

PPE (personal protective equipment)

dust mask type N95 (US), Eyeshields, Gloves

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