Chemistry:(2-Nitrophenyl)acetic acid

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Short description: Chemical compound


(2-Nitrophenyl)acetic acid
Styrene
2-Nitrophenylacetic acid.png
2-Nitrophenylacetic Acid Space Filling.png
Borginson.png
Names
IUPAC name
2-(2-nitrophenyl)acetic acid [2]
Other names
Benzeneacetic acid, 2-nitro-[1]
o-Nitrophenylacetic acid
2-nitrophenylacetic acid
(ortho-Nitrophenyl)acetic acid
acetic acid, (o-nitrophenyl)
2-(o-nitrophenyl)acetic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 223-128-0
UNII
Properties
C8H7NO4
Molar mass 181.15 g/mol
Appearance Yellow to Pale Brown Crystalline Powder
Density 1.4 g/cm3[3]
Boiling point 141 °C (286 °F; 414 K)
0.1417% (20 °C)[4]
Hazards
Main hazards Irritant
Safety data sheet MSDS
GHS pictograms GHS07: HarmfulGHS08: Health hazard
GHS Signal word Warning
H315, H319, H335, H341
P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P319Script error: No such module "Preview warning".Category:GHS errors, P321, P317Script error: No such module "Preview warning".Category:GHS errors, P332, P362+364Script error: No such module "Preview warning".Category:GHS errors, P403+233, P405, P501
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
0
2
0
Related compounds
Related derivatives;
related aromatic compounds
 phenylacetic acid,4-nitrophenylacetic acid;
4-nitrophenol,
2-nitrodiphenylamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Tracking categories (test):

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.[5]Blong.png

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.[6]
Protection and Deprotection of Primary Alcohols using 2-nitrophenylacetic acid.


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.[7][8] Partial reductive cyclization of the acids using weaker reducing agents forms hydroxamic acids.[8]

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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.[9] Quindoline synthesis.png

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.[10] 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.
Outside of organic synthesis, 2-nitrophenylacetic acid has been used as an herbicide, as it displays selective herbicidal properties.[11] 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. [12]

References

  1. ↑ "Benzeneacetic acid, 2-nitro-". https://webbook.nist.gov/cgi/cbook.cgi?ID=3740-52-1. 
  2. ↑ "2-Nitrophenylacetic acid (compound)". National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/77337#section=Names-and-Identifiers. 
  3. ↑ "AJ1130000". https://www.chemspider.com/Chemical-Structure.69754.html?rid=3a5361a1-eefa-4909-9499-b988e7838fcd#suppInfoTab. 
  4. ↑ Zhou, Yanyan; Wu, Jiaxin; Wang, Jian; Zhao, Hongkun (13 August 2020). "Equilibrium Solubility and Dissolution Property Analysis of 2-Nitrophenylacetic Acid in 13 Pure Solvents at Elevated Temperatures". Journal of Chemical & Engineering Data 65 (8): 4157–4165. doi:10.1021/acs.jced.0c00543. 
  5. ↑ Sohail, Muhammad; Raza, Abdul Rauf (February 2012). "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 30 (2): 353–356. doi:10.1002/cjoc.201180458. 
  6. ↑ Daragics, Katalin; Fügedi, Péter (7 May 2010). "(2-Nitrophenyl)acetyl: A New, Selectively Removable Hydroxyl Protecting Group". Organic Letters 12 (9): 2076–2079. doi:10.1021/ol100562f. PMID 20361745. 
  7. ↑ Wright, William B.; Collins, Kenneth H. (January 1956). "Cyclic Hydroxamic Acids Derived from Indole" (in en). Journal of the American Chemical Society 78 (1): 221–224. doi:10.1021/ja01582a061. ISSN 0002-7863. https://pubs.acs.org/doi/abs/10.1021/ja01582a061. 
  8. ↑ 8.0 8.1 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" (in en). Tetrahedron Letters 58 (6): 582–585. doi:10.1016/j.tetlet.2017.01.008. ISSN 0040-4039. https://www.sciencedirect.com/science/article/pii/S0040403917300084. 
  9. ↑ 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" (in en). Bioorganic & Medicinal Chemistry Letters 15 (20): 4560–4563. doi:10.1016/j.bmcl.2005.06.097. ISSN 0960-894X. PMID 16087333. https://www.sciencedirect.com/science/article/pii/S0960894X0500867X. 
  10. ↑ Vaidya, Sagar; Argade, Narshinha (2016-05-17). "Synthesis of (–)-Phaitanthrin D and (+)-Dihydropyrroloindoloquinazolinone" (in en). Synthesis 48 (17): 2896–2903. doi:10.1055/s-0035-1562098. ISSN 0039-7881. http://www.thieme-connect.de/DOI/DOI?10.1055/s-0035-1562098. 
  11. ↑ Back, Gayle E.; Dahle, Norman A. (July 6, 1971). "NITROPHENYLACETIC ACID DERVATIVES". https://patentimages.storage.googleapis.com/93/fb/dc/5c755cf73a191f/US3591623.pdf. 
  12. ↑ 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" (in en). Journal of Pharmaceutical and Biomedical Analysis 3 (5): 469–475. doi:10.1016/0731-7085(85)80062-5. ISSN 0731-7085. PMID 16867660. https://dx.doi.org/10.1016/0731-7085%2885%2980062-5. 



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