3-Nitrocinnamic acid

Base Information

• Chemical Name: 3-Nitrocinnamic acid
• CAS No.: 1772-76-5
• Molecular Formula: C9H7NO4
• Molecular Weight: 193.16
• European Community (EC) Number: 209-104-2
• UNII: Z5WU65J930
• DSSTox Substance ID: DTXSID8060298,DTXSID40901345
• Nikkaji Number: J95.669D,J9.876K
• Wikidata: Q27128558
• Metabolomics Workbench ID: 61239
• ChEMBL ID: CHEMBL1771753
• Mol file: 1772-76-5.mol

Synonyms:3-nitrobenzenepropenoic acid;Cinnamic acid, m-nitro-;m-nitrocinnamic acid

Chemical Property of 3-Nitrocinnamic acid

Chemical Property:

• Melting Point: 200-202 °C(lit.)
• Boiling Point: 372.1 °C at 760 mmHg
• Flash Point: 166.5 °C
• PSA: 83.12000
• Density: 1.411 g/cm³
• LogP: 2.21580
• Solubility.: slightly sol. in Alcohol
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 193.03750770
• Heavy Atom Count: 14
• Complexity: 256

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2E)-3-(3-Nitrophenyl)acrylicAcid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC(=CC(=C1)[N+](=O)[O-])C=CC(=O)O
• Isomeric SMILES: C1=CC(=CC(=C1)[N+](=O)[O-])/C=C/C(=O)O

Technology Process of 3-Nitrocinnamic acid

There total 55 articles about 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: 98.0%

malonic acid (141-82-2) + 3-nitro-benzaldehyde (99-61-6) → (E)-3-Nitrocinnamic acid (555-68-0,1772-76-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-amino propanoic acid; In ethanol; at 20 ℃; stereoselective reaction;

DOI:10.1002/cjoc.201180455

Reference yield: 96.5%

m-iodonitrobenzene (645-00-1) + acrylic acid (79-10-7) → (E)-3-Nitrocinnamic acid (555-68-0,1772-76-5)

Guidance literature:

With sodium carbonate; In water; at 120 ℃; for 12h; Green chemistry;

DOI:10.1002/aoc.5226

Reference yield: 92.0%

malonic acid (141-82-2) + sodium α-hydroxy-m-nitrotoluene-α-sulphonate (68444-12-2) → (E)-3-Nitrocinnamic acid (555-68-0,1772-76-5)

Guidance literature:

With piperazine; In ethylene glycol; for 0.125h; microwave irradiation;

upstream raw materials:

2,3-dibromo-3-(3-nitro-phenyl)-propionic acid ethyl ester

acetic anhydride

3-nitro-benzaldehyde

malonic acid

Downstream raw materials:

bis-[4-(3-nitro-trans-cinnamoyloxy)-phenyl]-sulfone

3'-nitro-2-methoxy-trans-stilbene

1-methyl-4-[2-(3-nitrophenyl)ethenyl]benzene

(E)-3,4’-dinitrostilbene

Refernces

• 1、 Varadwaj, G. Bishwa Bidita,Rana, Surjyakanta,Parida. "Amine functionalized K10 montmorillonite: A solid acid-base catalyst for the Knoevenagel condensation reaction". . p. 5122 - 5129. Retrieved 2013.
• 2、 Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei. "Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation". supporting information. p. 5905 - 5908. Retrieved 2021/06/18.
• 3、 Ghafary, Shahrzad,Ghobadian, Roshanak,Mahdavi, Mohammad,Nadri, Hamid,Moradi, Alireza,Akbarzadeh, Tahmineh,Najafi, Zahra,Sharifzadeh, Mohammad,Edraki, Najmeh,Moghadam, Farshad Homayouni,Amini, Mohsen. "Design, synthesis, and evaluation of novel cinnamic acid-tryptamine hybrid for inhibition of acetylcholinesterase and butyrylcholinesterase". . p. 463 - 477. Retrieved 2020/05/25.