(2-Nitrophenyl)acetic acid

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
(2-Nitrophenyl)acetic acid
Styrene
Styrene
Names
Preferred IUPAC name
(2-Nitrophenyl)acetic acid
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
2-(2-nitrophenyl)acetic acid[2]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.021.026 Edit this at Wikidata
EC Number
  • 223-128-0
UNII
  • InChI=1S/C8H7NO4/c10-8(11)5-6-3-1-2-4-7(6)9(12)13/h1-4H,5H2,(H,10,11) checkY
  • C1=CC=C(C(=C1)CC(=O)O)[N+](=O)[O-]
Properties
C8H7NO4
Molar mass 181.15 g/mol
Appearance Yellow to Pale Brown Crystalline Powder
Density 1.4 g/cm3[3]
Boiling point 141 Â°C (286 Â°F; 414 K)
0.1417% (20 Â°C)[4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant
GHS labelling:
GHS07: Exclamation markGHS08: Health hazard
Warning
H315, H319, H335, H341
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P332, P362+P364, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
Safety data sheet (SDS) MSDS
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 Â°C [77 Â°F], 100 kPa).
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Synthesis

This compound may be prepared by the nitration of phenylacetic acid.[5]

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]

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]

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

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