4-Nitrocinnamic acid

Base Information

• Chemical Name: 4-Nitrocinnamic acid
• CAS No.: 882-06-4
• Molecular Formula: C9H7 N O4
• Molecular Weight: 193.159
• Hs Code.: 2916 39 90
• European Community (EC) Number: 210-617-9,212-924-3
• NSC Number: 638142,2067
• DSSTox Substance ID: DTXSID1060710,DTXSID301043547
• Nikkaji Number: J62.844A,J95.670H
• ChEMBL ID: CHEMBL99068
• Mol file: 882-06-4.mol

Synonyms:4-Nitrocinnamic acid;619-89-6;3-(4-Nitrophenyl)acrylic acid;882-06-4;p-Nitrocinnamic acid;(E)-3-(4-Nitrophenyl)acrylic acid;2-Propenoic acid, 3-(4-nitrophenyl)-;Cinnamic acid, p-nitro-;trans-4-Nitrocinnamic acid;(E)-3-(4-nitrophenyl)prop-2-enoic acid;(2E)-3-(4-nitrophenyl)prop-2-enoic acid;3-(4-Nitrophenyl)propenoic acid;NSC 2067;2-Propenoic acid, 3-(4-nitrophenyl)-, (2E)-;CCRIS 1665;EINECS 210-617-9;MFCD00007381;(E)-p-Nitrocinnamic acid;3-(4-Nitrophenyl)-2-propenoic acid;EINECS 212-924-3;NSC638142;(2E)-3-(4-Nitrophenyl)Acrylic Acid;Akos 369;3-{4-nitrophenyl}acrylic acid;3-(4-nitrophenyl)prop-2-enoic acid;Para-nitrocinnamic acid;trans-4-nitrocinnamicacid;trans-4-Nitrocinnmic acid;4-Nitrobenzeneacrylic acid;SCHEMBL42325;CHEMBL99068;SCHEMBL277169;DTXSID1060710;XMMRNCHTDONGRJ-ZZXKWVIFSA-;AMY4057;NSC2067;Cinnamic acid, p-nitro-, (E)-;DTXSID301043547;(E)-3-(4-Nitrophenyl)acrylicacid;E-3-(4-nitrophenyl)propenoic acid;NSC-2067;BBL009860;STK397302;AKOS000118870;AKOS040763592;CS-W015785;NSC-638142;NCGC00331331-01;4-Nitrocinnamic acid, predominantly trans;AC-20110;AS-10856;LS-54157;(E)-3-(4-nitrophenyl)-2-propenoic acid;BB 0290809;N0355;EN300-16974;3-(4-(Hydroxy(oxido)amino)phenyl)acrylic acid;EN300-364944;2-Propenoic acid, 3-(4-nitrophenyl)-, (E)-;4-Nitrocinnamic acid, predominantly trans, 97%;4-PROPYL-3-FLUOROBIPHENYL-4-BORONICACID;AB00376910-03;A833521;A862286;AE-641/00135027;J-650051;W-105061;Z56845264;F3284-8535

Chemical Property of 4-Nitrocinnamic acid

Chemical Property:

• Melting Point: 289 °C (dec.)(lit.)
• Boiling Point: 346℃
• PKA: pK1:4.05 (25°C)
• Flash Point: 154℃
• PSA: 83.12000
• Density: 1.411
• LogP: 2.21580
• Storage Temp.: Store below +30°C.
• Water Solubility.: Insoluble in water.
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 193.03750770
• Heavy Atom Count: 14
• Complexity: 248

Purity/Quality:

98%, ^*data from raw suppliers

4-Nitrocinnamic Acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC(=CC=C1C=CC(=O)O)[N+](=O)[O-]
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C(=O)O)[N+](=O)[O-]
• Uses: trans-4-Nitrocinnamic acid, is used as a raw material for saccharine. It is also used as a useful chemical for biological applications. Some other applications include it is used as an organic intermediate.

Technology Process of 4-Nitrocinnamic acid

There total 55 articles about 4-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: 100.0%

malonic acid (141-82-2) + 4-nitrobenzaldehdye (555-16-8) → 4-nitro-trans-cinnamic acid (882-06-4)

Guidance literature:

With pyridine; In ethanol; for 1.75h; Inert atmosphere; Reflux;

DOI:10.1002/chem.201101978

Reference yield: 98.0%

ethyl (E)-3-(4-nitrophenyl)-2-propenoate (24393-61-1) → 4-nitro-trans-cinnamic acid (882-06-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 25 ℃; for 24h;

DOI:10.1016/j.bmc.2021.116299

Reference yield: 96.0%

carbon tetrabromide (558-13-4) + 1-nitro-4-[(E)-2-nitroeth-1-enyl]benzene (3156-41-0,5576-98-7) → 4-nitro-trans-cinnamic acid (882-06-4)

Guidance literature:

With tris(2,2'-bipyridyl)ruthenium dichloride; water; diisopropylamine; In acetonitrile; at 20 ℃; for 10h; stereoselective reaction; Inert atmosphere; Irradiation;

DOI:10.1039/c7nj04578f

upstream raw materials:

quinoline

malonic acid

4-nitrobenzaldehdye

(E)-3-phenylacrylic acid

Downstream raw materials:

2-methyl-6-(4-nitro-styryl)-benzothiazole

trans-4,4'-dinitrostilbene

2,3-dibromo-3-(4-nitro-phenyl)-propionic acid

(2RS,3SR)-2,3-dibromo-3-(4-nitrophenyl)propanoic acid

Refernces

• 1、 Baruch, Yifat,Gopas, Jacob,Kadosh, Yael,Kumar, Rajendran Saravana,Kushmaro, Ariel,Muthuraman, Subramani,Yaniv, Karin. "Quorum sensing and nf-κb inhibition of synthetic coumaperine derivatives from piper nigrum". supporting information. . Retrieved 2021/05/28.
• 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.