(Z)-Methyl 2-acetamido-3-(4-nitrophenyl)acrylate

Base Information

• Chemical Name: (Z)-Methyl 2-acetamido-3-(4-nitrophenyl)acrylate
• CAS No.: 105962-57-0
• Molecular Formula: C12H12N2O5
• Molecular Weight: 264.238
• DSSTox Substance ID: DTXSID601193119
• Nikkaji Number: J1.054.628A,J1.488.927B
• Mol file: 105962-57-0.mol

Synonyms:105962-57-0;(Z)-METHYL 2-ACETAMIDO-3-(4-NITROPHENYL)ACRYLATE;alpha-(Acetylamino)-4-nitrocinnamic acid methyl ester;SCHEMBL13906643;DTXSID601193119;AKOS003245502;N-Acetyl-2-(4-nitrobenzylidene)glycine methyl ester;METHYL 2-(ACETYLAMINO)-3-(4-NITROPHENYL)ACRYLATE;Methyl (2Z)-2-(acetylamino)-3-(4-nitrophenyl)-2-propenoate

Chemical Property of (Z)-Methyl 2-acetamido-3-(4-nitrophenyl)acrylate

Chemical Property:

• PSA: 101.22000
• LogP: 2.15890
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 264.07462149
• Heavy Atom Count: 19
• Complexity: 391

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(=CC1=CC=C(C=C1)[N+](=O)[O-])C(=O)OC
• Isomeric SMILES: CC(=O)N/C(=C\C1=CC=C(C=C1)[N+](=O)[O-])/C(=O)OC

Technology Process of (Z)-Methyl 2-acetamido-3-(4-nitrophenyl)acrylate

There total 5 articles about (Z)-Methyl 2-acetamido-3-(4-nitrophenyl)acrylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 67.0%

methanol (67-56-1) + 4-nitrobenzaldehdye (555-16-8) + N-acetylglycine (543-24-8) → (Z)-methyl 2-acetamido-3-(4-nitrophenyl)acrylate (105962-57-0)

Guidance literature:

N-acetylglycine; With chloroformic acid ethyl ester; triethylamine; In benzene; at 0 - 20 ℃;

4-nitrobenzaldehdye; In benzene; at 80 ℃; for 2h;

methanol; With triethylamine; at 65 ℃; for 3h;

DOI:10.1039/d0ob00557f

Reference yield: 56.0%

p-nitrobenzene iodide (636-98-6) + Methyl 2-acetamidoacrylate (35356-70-8) → (Z)-methyl 2-acetamido-3-(4-nitrophenyl)acrylate (105962-57-0)

Guidance literature:

With tetrabutyl-ammonium chloride; sodium hydrogencarbonate; palladium diacetate; In N,N-dimethyl-formamide; at 85 ℃; for 40h;

Reference yield: 48.0%

(Z)-2-methyl-4-(4-nitrobenzylidene)oxazol-5(4H)-one (66949-13-1) + sodium methylate (124-41-4) → (Z)-methyl 2-acetamido-3-(4-nitrophenyl)acrylate (105962-57-0)

Guidance literature:

In methanol; at 20 ℃; for 3h;

DOI:10.1002/anie.201412098

upstream raw materials:

p-nitrobenzene iodide

Methyl 2-acetamidoacrylate

para-nitrophenyl bromide

4-nitrobenzaldehdye

Downstream raw materials:

cis-4-p-nitrophenyl-3-acetamido-3-carbomethoxy-Δ¹-pyrazoline

methyl (R)-2-acetamido-3-(4-nitrophenyl)propanoate

(S)-methyl 2-acetamido-3-(4-nitrophenyl)propanoate

4-(4-Nitro-phenyl)-1H-pyrazole-3-carboxylic acid