317519

Methyl 2-acetamidoacrylate

98%

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

Properties

• 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.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: 235.4 °F - closed cup
• flash_point_c: 113 °C - closed cup
• ppe: dust mask type N95 (US), Eyeshields, Gloves