cis-m-Nitrocinnamic acid

Base Information

• Chemical Name: cis-m-Nitrocinnamic acid
• CAS No.: 555-68-0
• Molecular Formula: C9H7NO4
• Molecular Weight: 193.159
• Hs Code.: 29163900
• NSC Number: 5408
• UNII: Y0G9LX8N55
• DSSTox Substance ID: DTXSID001279309
• Nikkaji Number: J1.165.838E
• Wikidata: Q27294102
• Mol file: 555-68-0.mol

Synonyms:cis-m-Nitrocinnamic acid;3-Nitrocinnamic acid, (Z)-;Cinnamic acid, m-nitro-, (Z)-;5676-61-9;UNII-Y0G9LX8N55;3-Nitrocinnamic acid, (Z)-form [MI];Y0G9LX8N55;2-Propenoic acid, 3-(3-nitrophenyl)-, (2Z)-;NSC-5408;2-Propenoic acid, 3-(3-nitrophenyl)-;(Z)-3-nitrocinnamic acid;SCHEMBL4179178;NSC5408;DTXSID001279309;(2Z)-3-(3-Nitrophenyl)-2-propenoic acid;2-Propenoic acid, 3-(3-nitrophenyl)-, (Z)-;Q27294102

Chemical Property of cis-m-Nitrocinnamic acid

Chemical Property:

• Appearance/Colour: Light yellow fine crystalline powder
• Vapor Pressure: 3.39E-06mmHg at 25°C
• Melting Point: 200-202 °C(lit.)
• Refractive Index: 1.5200 (estimate)
• Boiling Point: 372.1 °C at 760 mmHg
• PKA: pK1:4.12 (25°C)
• Flash Point: 166.5 °C
• PSA: 83.12000
• Density: 1.411 g/cm³
• LogP: 2.21580
• Storage Temp.: Sealed in dry,Room Temperature
• 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:

99% ^*data from raw suppliers

3-NitrocinnamicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• 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 cis-m-Nitrocinnamic acid

There total 50 articles about cis-m-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:

3-(3-nitrophenyl)acrylic acid methyl ester

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

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

3,3'-dinitro-trans-stilbene

Refernces

• 1、 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.
• 2、 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.