4-Nitrophenylacetic acid

Base Information

• Chemical Name: 4-Nitrophenylacetic acid
• CAS No.: 104-03-0
• Molecular Formula: C8H7NO4
• Molecular Weight: 181.148
• Hs Code.: 29163900
• European Community (EC) Number: 203-168-5
• NSC Number: 5398
• UNII: KLB4P626RE
• DSSTox Substance ID: DTXSID6059289
• Nikkaji Number: J714.504G,J10.498A
• Wikidata: Q27096559
• Metabolomics Workbench ID: 150512
• Mol file: 104-03-0.mol

Synonyms:2-(4-nitrophenoxy)acetic acid;4-nitrobenzeneacetic acid;4-nitrophenylacetic acid

Chemical Property of 4-Nitrophenylacetic acid

Chemical Property:

• Appearance/Colour: beige to yellow crystalline powder
• Vapor Pressure: 2.26E-06mmHg at 25°C
• Melting Point: 153-156 °C
• Refractive Index: 1.5468 (estimate)
• Boiling Point: 377.6 °C at 760 mmHg
• PKA: 3.85(at 25℃)
• Flash Point: 171.6 °C
• PSA: 83.12000
• Density: 1.407 g/cm³
• LogP: 1.74510
• Storage Temp.: Store below +30°C.
• Water Solubility.: slightly soluble
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 181.03750770
• Heavy Atom Count: 13
• Complexity: 203

Purity/Quality:

99% ^*data from raw suppliers

4-Nitrophenylacetic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC(=CC=C1CC(=O)O)[N+](=O)[O-]
• Uses: Intermediate for dyestuffs, pharmaceuticals, penicillin precursors, local anesthetics. (4-Nitrophenyl)acetic Acid used in the synthesis of 5,7-dimethyl-2-aryl-3H-pyrrolizin-3-ones which may act as angiogenesis inhibitors. Also used in the one step construction of amino-substituted squaraine dye.

Technology Process of 4-Nitrophenylacetic acid

There total 78 articles about 4-Nitrophenylacetic 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: 60.0%

C16H15NO5S → 4-nitrobenzeneacetic acid (104-03-0) + 4-nitro-benzoic acid (62-23-7)

Guidance literature:

With ammonium cerium (IV) nitrate; oxygen; In acetonitrile; at 20 - 50 ℃; for 4h;

DOI:10.1016/j.tetlet.2014.08.038

Reference yield:

p-nitrophenyl p-nitrophenylacetate (35665-94-2) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 4-nitrobenzeneacetic acid (104-03-0)

Guidance literature:

With barium dihydroxide; In water; dimethyl sulfoxide; at 30 ℃; Rate constant; Mechanism;

DOI:10.1021/jo00319a028

Reference yield:

N-Methyl-2,N-bis-(4-nitro-phenyl)-acetamide (75990-87-3) → 4-nitrobenzeneacetic acid (104-03-0) + N-methyl(p-nitroaniline) (100-15-2)

Guidance literature:

With barium dihydroxide; In water; dimethyl sulfoxide; at 30 ℃; Rate constant; Mechanism;

DOI:10.1021/jo00319a028

upstream raw materials:

phenylacetic acid

diethyl ether

1-methyl-4-nitrosobenzene

2-(4-nitrophenyl)malonic acid dimethyl ester

Downstream raw materials:

4-dimethylamino-4'-nitrostilbene

trans-4,4'-dinitrostilbene

4,4'-dinitro stilbene

2,3t-bis-(4-nitro-phenyl)-acrylic acid

Refernces

• 1、 Sohail, Muhammad,Raza, Abdul Rauf. "A novel one pot synthesis of o-nitrophenylacetic acid and unexpected p-nitrobenzoic acid by HNO3-mediated CH2 extrusion reaction of phenylacetic acid". . p. 353 - 356. Retrieved 2012.
• 2、 Benvidi, Ali,Ghobadi, Kobra,Khoshro, Hossein,Mohammadzadeh, Safoora,Zare, Hamid R.. "The electrochemical behavior of 4-nitrobenzyl bromide and its catalytic activity for reduction of CO2 in the acetonitrile solvent at the Cu/Pd/rGO/GCE surface". . . Retrieved 2020.
• 3、 Hornum, Mick,Mulberg, Mads W.,Szomek, Maria,Reinholdt, Peter,Brewer, Jonathan R.,Wüstner, Daniel,Kongsted, Jacob,Nielsen, Poul. "Substituted 9-Diethylaminobenzo[ a]phenoxazin-5-ones (Nile Red Analogues): Synthesis and Photophysical Properties". . p. 1471 - 1488. Retrieved 2021.
• 4、 Winkler, Robert,Richter, Martin E. A.,Knuepfer, Uwe,Merten, Dirk,Hertweck, Christian. "Regio- and chemoselective enzymatic N-oxygenation in vivo, in vitro, and in flow". . p. 8016 - 8018. Retrieved 2006.
• 5、 Wakuluk-Machado, Anne-Marie,Dewez, Damien F.,Baguia, Hajar,Imbratta, Miguel,Echeverria, Pierre-Georges,Evano, Gwilherm. "Pd(OH)2/C, a Practical and Efficient Catalyst for the Carboxylation of Benzylic Bromides with Carbon Monoxide". . p. 713 - 723. Retrieved 2020/02/04.