4-Amino-3-nitrocinnamic acid

Base Information

• Chemical Name: 4-Amino-3-nitrocinnamic acid
• CAS No.: 51794-06-0
• Molecular Formula: C₉H₈N₂O₄
• Molecular Weight: 208.174
• European Community (EC) Number: 851-534-3
• Mol file: 51794-06-0.mol

Synonyms:4-Amino-3-nitrocinnamic acid;51794-06-0;(2E)-3-(4-Amino-3-nitrophenyl)prop-2-enoic acid;(E)-3-(4-amino-3-nitrophenyl)prop-2-enoic acid;24364-02-1;3-(4-amino-3-nitrophenyl)prop-2-enoic acid;SCHEMBL2910060;SCHEMBL2910064;BCA79406;3-(4-Amino-3-nitrophenyl)acrylic acid;(E)-3-(4-Amino-3-nitrophenyl)acrylic acid;EN300-206058;EN300-833113

Chemical Property of 4-Amino-3-nitrocinnamic acid

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 208.04840674
• Heavy Atom Count: 15
• Complexity: 284

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C=CC(=O)O)[N+](=O)[O-])N
• Isomeric SMILES: C1=CC(=C(C=C1/C=C/C(=O)O)[N+](=O)[O-])N

Technology Process of 4-Amino-3-nitrocinnamic acid

There total 3 articles about 4-Amino-3-nitrocinnamic acid 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: 90.0%

4-Acetamido-3-nitrocinnamic acid (106873-46-5) → 4-Amino-3-nitrocinnamic acid (51794-06-0)

Guidance literature:

With sodium hydroxide; In methanol; Ambient temperature;

Reference yield:

(E)-4-chloro-3-nitrocinnamic acid (20797-48-2,199679-38-4) → 4-Amino-3-nitrocinnamic acid (51794-06-0)

Guidance literature:

With ammonia; triethylamine; In 1,4-dioxane; at 100 ℃;

DOI:10.1016/j.bmcl.2009.01.041

Reference yield:

4-acetamido-3-nitrobenzaldehyde (51818-98-5) → 4-Amino-3-nitrocinnamic acid (51794-06-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / pyridine / ethanol / 2 h / Heating

2: 90 percent / 10percent aq. NaOH / methanol / Ambient temperature

With pyridine; sodium hydroxide; In methanol; ethanol;

upstream raw materials:

4-Acetamido-3-nitrocinnamic acid

4-acetamido-3-nitrobenzaldehyde

(E)-4-chloro-3-nitrocinnamic acid

Downstream raw materials:

(E)-methyl 3-(4-amino-3-nitrophenyl)acrylate

3,4-Diaminocinnamic acid