317519
Methyl 2-acetamidoacrylate
98%
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About This Item
Linear Formula:
H2C=C(NHCOCH3)CO2CH3
CAS Number:
Molecular Weight:
143.14
NACRES:
NA.23
PubChem Substance ID:
UNSPSC Code:
12162002
MDL number:
Product Name
Methyl 2-acetamidoacrylate, 98%
InChI
1S/C6H9NO3/c1-4(6(9)10-3)7-5(2)8/h1H2,2-3H3,(H,7,8)
SMILES string
COC(=O)C(=C)NC(C)=O
InChI key
SMWNFFKPVLVOQQ-UHFFFAOYSA-N
assay
98%
bp
104 °C/8 mmHg (lit.)
mp
50-52 °C (lit.)
Quality Level
Related Categories
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.
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.
signalword
Warning
hcodes
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
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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William P Hems et al.
Organic & biomolecular chemistry, 3(8), 1547-1550 (2005-04-14)
Rh diphosphine complexes using DuPhos and JosiPhos as chiral ligands have been immobilised by ion exchange into the mesoporous material MCM-41. When used as catalysts for the enantioselective hydrogenation of dimethyl itaconate and methyl-2-acetamidoacrylate, these heterogeneous catalysts give catalytic performance
RhIII?Catalyzed Oxidative Olefination of Vinylic C H Bonds: Efficient and Selective Access to Di?unsaturated ??Amino Acid Derivatives and Other Linear 1, 3?Butadienes.
Besset T, et al.
European Journal of Chemistry, 17(26), 7167-7171 (2011)
Orthogonal synthesis of indolines and isoquinolines via aryne annulation.
Christopher D Gilmore et al.
Journal of the American Chemical Society, 130(5), 1558-1559 (2008-01-16)
Penny L Sappington et al.
Biochemical pharmacology, 70(11), 1579-1592 (2005-10-18)
Ethyl pyruvate (EP) is a simple aliphatic ester derived from the endogenous metabolite, pyruvic acid. EP has been shown to decrease the expression of various pro-inflammatory mediators, including nitric oxide (NO*), tumor necrosis factor (TNF), cyclooxygenase-2, and interleukin (IL)-6, in
Synthesis of 2-methyl- and 2-methylenecyclobutane amino acids
Avenoza A, et al.
Tetrahedron, 61(16), 4165-4172 (2005)
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