(2-Nitrophenyl)acetic acid

Chemical compound May 2023 July 2020 changed changed 477173358 (2-Nitrophenyl)acetic acid 2-Nitrophenylacetic Acid Structure.png 150px 2-Nitrophenylacetic acid.png 180px 2-Nitrophenylacetic Acid Space Filling.png Borginson.png Styrene (2-Nitrophenyl)acetic acid Benzeneacetic acid, 2-nitro-https://webbook.nist.gov/cgi/cbook.cgi?ID=3740-52-1 NIST Chemistry WebBook, SRD 69 Benzeneacetic acid, 2-nitro-o-Nitrophenylacetic acid2-nitrophenylacetic acid(ortho-Nitrophenyl)acetic acidacetic acid, (o-nitrophenyl)2-(o-nitrophenyl)acetic acid2-(2-nitrophenyl)acetic acidhttps://pubchem.ncbi.nlm.nih.gov/compound/77337#section=Names-and-Identifiers PubChem National Library of Medicine 14 May 2023 2-Nitrophenylacetic acid (compound) correct CAS 3740-52-1 correct chemspider 69754 correct EBI 187870 223-128-0 77337 correct FDA 05TN0SUY38 correct chemspider 1S/C8H7NO4/c10-8(11)5-6-3-1-2-4-7(6)9(12)13/h1-4H,5H2,(H,10,11) C1=CC=C(C(=C1)CC(=O)O)[N+](=O)[O-] C8H7NO4 181.15 g/mol Yellow to Pale Brown Crystalline Powder 1.4 g/cm3AJ1130000 https://www.chemspider.com/Chemical-Structure.69754.html?rid=3a5361a1-eefa-4909-9499-b988e7838fcd#suppInfoTab ChemSpider 14 May 2023 0.1417% (20 °C)Zhou Yanyan Wu Jiaxin Wang Jian Zhao Hongkun Equilibrium Solubility and Dissolution Property Analysis of 2-Nitrophenylacetic Acid in 13 Pure Solvents at Elevated Temperatures Journal of Chemical & Engineering Data 13 August 2020 65 8 4157–4165 10.1021/acs.jced.0c00543 225475559 141 MSDS Irritant 0 2 0 07 08 Warning 315 319 335 341 261 264 271 280 302+352 304+340 305+351+338 319 321 317 332 362+364 403+233 405 501 derivatives;related aromatic compounds phenylacetic acid,4-nitrophenylacetic acid; 4-nitrophenol,2-nitrodiphenylamine 2-Nitrophenylacetic acid is an organic compound used in organic synthesis that has also been used as an herbicide. It is a derivative of phenylacetic acid, containing a phenyl functional group, a carboxylic acid functional group, and a nitro functional group. It is an important reagent for many organic reactions, especially for the formation of heterocycles. Synthesis This compound may be prepared by the nitration of phenylacetic acid.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 Chinese Journal of Chemistry February 2012 30 2 353–356 10.1002/cjoc.201180458320x320px Applications In organic synthesis, 2-nitrophenylacetic acid can be used as a protecting group for primary alcohols. The alcohol is esterified with 2-nitrophenylacetic acid, proceeding through the acid chloride or acid anhydride. The acid itself can also protect the alcohol through the Mitsunobu reaction: reacting the alcohol and the acid with diethyl azidocarboxylate and triphenylphosphine in dichloromethane. The protecting group is selectively removed using zinc and ammonium chloride, and is compatible with other existing alcohol protecting groups.Daragics Katalin Fügedi Péter (2-Nitrophenyl)acetyl: A New, Selectively Removable Hydroxyl Protecting Group Organic Letters 7 May 2010 12 9 2076–2079 10.1021/ol100562f 20361745 Protection and Deprotection of Primary Alcohols using 2-nitrophenylacetic acid.|475x475px In addition, 2-nitrophenylacetic acid is a precursor for many heterocycles. Complete reduction of 2-nitrophenylacetic acid yields anilines, which quickly cyclize to form lactams.Wright William B. Collins Kenneth H. January 1956 Cyclic Hydroxamic Acids Derived from Indole https://pubs.acs.org/doi/abs/10.1021/ja01582a061 Journal of the American Chemical Society en 78 1 221–224 10.1021/ja01582a061 0002-7863 subscription Ichire Ogar Jans Petra Parfenov Galina Dounay Amy B. 2017-02-08 A safe and selective method for reduction of 2-nitrophenylacetic acid systems to N-aryl hydroxamic acids using continuous flow hydrogenation https://www.sciencedirect.com/science/article/pii/S0040403917300084 Tetrahedron Letters en 58 6 582–585 10.1016/j.tetlet.2017.01.008 0040-4039 subscription Partial reductive cyclization of the acids using weaker reducing agents forms hydroxamic acids. 505x505px Both of these processes are useful in the synthesis of many biologically active molecules. 2-nitrophenylacetic acid is a precursor of quindoline, which although it does not have many practical applications on its own, quindoline derivatives and modifications can be treated as enzyme inhibitors and anticancer agents.Singer Jamie M. Barr Bridget M. Coughenour Linda L. Gregory Tracy F. Walters Michael A. 2005-10-15 8-Substituted 3,4-dihydroquinolinones as a novel scaffold for atypical antipsychotic activity https://www.sciencedirect.com/science/article/pii/S0960894X0500867X Bioorganic & Medicinal Chemistry Letters en 15 20 4560–4563 10.1016/j.bmcl.2005.06.097 16087333 0960-894X subscription 650px Derivatives of 2-nitrophenylacetic acids are useful in total synthesis for their ability to form heterocycles. 2-nitrophenylacetic acid is a precursor to (−)-phaitanthrin D, a clinically useful molecule originally isolated from the Phaius mishmensis orchid.Vaidya Sagar Argade Narshinha 2016-05-17 Synthesis of (–)-Phaitanthrin D and (+)-Dihydropyrroloindoloquinazolinone http://www.thieme-connect.de/DOI/DOI?10.1055/s-0035-1562098 Synthesis en 48 17 2896–2903 10.1055/s-0035-1562098 99029333 0039-7881 subscription The carboxylic acid on the 2-nitrophenylacetic acid is first protected using menthol, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCl), hydroxybenzotriazole(HOBt) and N,N-iisopropylethylamine(DIPEA). A pattern of reducing the nitro group to an amino group and subsequently forming amides by the addition to carboxylic acids (namely nitrobenzoic acid) occurs. Reductive cyclization of the subsequent product using hexamethyldisilazane, zinc chloride and dimethylformamide forms the disubstituted heterocycle present in the (−)-phaitantrin D molecule. Abbreviated Synthesis of (−)-phaitanthrin D.|650x650 px Outside of organic synthesis, 2-nitrophenylacetic acid has been used as an herbicide, as it displays selective herbicidal properties.Back Gayle E. Dahle Norman A. July 6, 1971 Nitrophenylacetic Acid Derivatives https://patentimages.storage.googleapis.com/93/fb/dc/5c755cf73a191f/US3591623.pdf United States Patent Office It has also been used as an internal standard for measurement of salicylamide-O-acetic acid (an anti-asthma drug) using high performance liquid chromatography.Schulz H. -U. Kraas E. 1985-01-01 Determination of the theophylline solubilizer salicylamide-O-acetic acid in serum and urine using high-performance liquid chromatography https://dx.doi.org/10.1016/0731-7085%2885%2980062-5 Journal of Pharmaceutical and Biomedical Analysis en 3 5 469–475 10.1016/0731-7085(85)80062-5 16867660 0731-7085 subscription References Category:Phenylacetic acids Category:2-Nitrophenyl compounds Category:Herbicides