6307-10-4

Basic information

• Product Name: 2-[(4-nitrophenyl)carbamoyl]benzoic acid
• Synonyms: 2-[(4-nitrophenyl)carbamoyl]benzoic acid
• CAS NO: 6307-10-4
• Molecular Formula: C₁₄H₁₀N₂O₅
• Molecular Weight: 286.24
• Mol File: 6307-10-4.mol

Chemical Properties

• Boiling Point: 436.7°C at 760 mmHg
• Flash Point: 217.9°C
• Appearance: /
• Density: 1.485g/cm³
• Vapor Pressure: 2.13E-08mmHg at 25°C
• Refractive Index: 1.697
• CAS DataBase Reference: 2-[(4-nitrophenyl)carbamoyl]benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(4-nitrophenyl)carbamoyl]benzoic acid(6307-10-4)
• EPA Substance Registry System: 2-[(4-nitrophenyl)carbamoyl]benzoic acid(6307-10-4)

Safety Data

• Hazardous Substances Data: 6307-10-4(Hazardous Substances Data)

Usage

Aromatic carboxylic acid

The compound belongs to the class of aromatic carboxylic acids, which are characterized by the presence of a carboxyl group (-COOH) attached to an aromatic ring, such as a benzene ring.

Nitro group

The compound contains a nitro group (-NO2) attached to a phenyl ring. A nitro group is a functional group consisting of an oxygen-nitrogen-oxygen bond (-O-N=O), which is known for its strong electron-withdrawing properties.

Carbamoyl group

2-[(4-nitrophenyl)carbamoyl]benzoic acid also contains a carbamoyl group (-NH2CO-) attached to a benzene ring. A carbamoyl group is a functional group consisting of an amide bond (-NH2) and a carbonyl group (-CO-), which can participate in various chemical reactions.

Building block in organic synthesis

The compound is commonly used in organic synthesis and research as a building block for creating various pharmaceuticals and other organic compounds. This means that it can be used as a starting material or intermediate in the synthesis of more complex molecules.

Valuable tool in chemistry and pharmaceutical research

The unique structure and properties of 2-[(4-nitrophenyl)carbamoyl]benzoic acid make it a valuable tool for the development of new materials and chemical compounds. This implies that it can be used to create novel compounds with potential applications in various fields, such as medicine, materials science, and more.

InChI:InChI=1/C14H10N2O5/c17-13(11-3-1-2-4-12(11)14(18)19)15-9-5-7-10(8-6-9)16(20)21/h1-8H,(H,15,17)(H,18,19)

Upstream product

• 85-44-9 phthalic anhydride 
• 100-01-6 4-nitro-aniline 
• 785-81-9 4-nitro-N-(phenylmethylene)benzenamine 
• 4727-29-1 phthalanilic acid 
• 31604-39-4 2-(4-nitrophenyl)isoindoline-1,3-dione 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 88-95-9 Phthaloyl dichloride 

Downstream Products

• 31604-39-4 2-(4-nitrophenyl)isoindoline-1,3-dione 
• 520-03-6 N-phenylphthalimide 
• 100-01-6 4-nitro-aniline 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 85-44-9 phthalic anhydride 
• 105536-74-1 Cr(C₆H₄COOCONHC₆H₄NO₂)3 
• 89183-98-2 {Co(NPA)2(H₂O)2} 

Relevant articles and documents

Compounds and methods for inducing chondrogenesis

The present invention provides compounds and compositions for the amelioration of arthritis and joint injuries by inducing mesenchymal stem cells into chondrocytes.

Water mediated, environmentally friendly, step-wise, tandem & one-pot syntheses of 2-(1H-benzo[d]imidazole-2-yl)-N-arylbenzamides

Water mediated and environmentally friendly, step-wise, tandem & one-pot syntheses of 2-(1H-benzo[d]imidazole-2-yl)-N-arylbenzamide derivatives have been developed by simply combining phthalic anhydride, anilines and phenylenediammonium dihydrogenphosphate. This reaction has an easy workup, provides excellent yields, and uses water as the solvent which is considered to be relatively environmentally benign.

Synthesis, spectral and biological studies of transition metal complexes of 2-(4-nitrophenylaminocarbonyl)benzoic acid

In this study Cr(III), Co(II), Ni(II), Cu(II) and Zn(II) complexes of 2-(4-nitrophenylaminocarbonyl)benzoic acid have been prepared and were characterized by physical, analytical and spectroscopic studies. On the basis of electronic spectra and magnetic susceptibility measurements in conjunction with infrared spectra, six coordinated octahedral structure has been proposed to Cr3+, Co3+ and Ni2+ complexes. In case of Cu2+ and Zn2+, they form four coordinated complexes. The ligand and its metal complexes have been tested for their in vitro antimicrobial activity against three bacterial strains, Mycobacterium smegmatis (gram +ve), Escherichia coli (gram -ve), Pseudomonas aeuroginosa (gram -ve) and three fungal strains, Nigrospora oryzae, Aspergillus niger and Candida albicans. The antimicrobial activities of the metal complexes were found to be more than those of 2-(4-nitrophenylaminocarbonyl)benzoic acid alone.

Synthesis, characterization and biological studies of 2-(4- Nitrophenylamino-carbonyl)benzoic acid and its complexes with Cr(III), Co(II), Ni(II), Cu(II) and Zn(II)

Cr(III), Co(II), Ni(II), Cu(II) and Zn(II) complexes of 2-(4-Nitrophenylaminocarbonyl)benzoic acid were synthesized and characterized on the basis of physical, analytical and spectroscopic data. The ligands, as well as its metal complexes were checked for their in-vitro antimicrobial activity against three bacterial strains, Mycobacterium smegmatis, Escherichia coli, Pseudomonas aeuroginosa, and three fungal strains, Nigrospora oryzae, Aspergillus niger and Candida albicans. Disc diffusion method and Tube diffusion test were used for antibacterial and antifungal activities, respectively. The synthesized complexes only show significant antifungal activity but inactive for antibacterial, however, in general, the metal complexes were found to be more active against antimicrobial activities as compared to their uncomplexed ligand.

The kinetic study on the effects of mixed aqueous-organic solvents on the rate of O- And N- cyclisation of N-(4′-nitrophenyl)phthalamic acid

The pseudo-first-order rate constants (kobs) for the intramolecular carboxylic group-assisted cleavage of N-(4′-nitrophenyl) phthalamic acid (1) show nonlinear decrease of - 17-fold and - 117-fold with the increase in the respective contents Of CH3CN (10-80% v/v) and 1,4-dioxan (9.5-79.4% v/v) in mixed aqueous solvents. The fraction of Ncyclization of 1 leading to the formation of N-(4′-nitrophenyl) phthalimide, 2, remains almost zero at ≤40% v/v CH3CN while it increases from 0.06 to 0.49 with increase in CH3CN content (50-80% v/v) at 1.0x10-3 M HCl. However, the observed data reveal an almost absence of N-cyclization within 1,4-dioxan content range 10-80% v/v.

π-Stacked hydrogen-bonded dimers in 2-(2-nitrophenylaminocarbonyl)-benzoic acid, and hydrogen-bonded sheets in orthorhombic and monoclinic polymorphs of 2-(4-nitrophenylaminocarbonyl)benzoic acid

Molecules of 2-(2-nitrophenylaminocarbonyl)benzoic acid, C 14H10N2O5, are linked into centrosymmetric R22(8) dimers by a single O-H...O hydrogen bond [H...O = 1.78 A, O...O = 2.623 (2) A and O-H...O = 178°] and these dimers are linked into sheets by a single aromatic π-π stacking interaction. The isomeric compound 2-(4-nitrophenylamino-carbonyl)benzoic acid crystallizes in two polymorphic forms. In the orthorhombic form (space group P21212 1 with Z′ = 1, crystallized from ethanol), the molecules are linked into sheets of R44(22) rings by a combination of one N-H...O hydrogen bond [H...O = 1.96 A, N...O = 2.833 (3) A and N-H...O = 171°] and one O-H...O hydrogen bond [H...O = 1.78 A, O...O = 2.614 (3) A and O-H...O = 173°]. In the monoclinic form (space group P21/n with Z′ = 2, crystallized from acetone), the molecules are linked by a combination of two N-H...O hydrogen bonds [H...O = 2.09 and 2.16 A, N...O = 2.873 (4) and 2.902 (3) A, and N-H...O = 147 and 141°] and two O-H...O hydrogen bonds [H...O = 1.84 and 1.83 A, O...O = 2.664 (3) and 2.666 (3) A, and O-H...O = 166 and 174°] into sheets of some complexity. These sheets are linked into a three-dimensional framework by a single C-H...O hydrogen bond [H...O = 2.45 A, C...O = 3.355 (4) A and C-H...O = 160°].

The cyclisation of substituted phthalanilic acids in acetic acid solution. A kinetic study of substituted N-phenylphthalimide formation

One novel and ten known substituted 3′- and 4′-phthalanilic acids have been prepared. These have been cyclised to two novel and nine known substituted N-phenylphthalimides by heating with glacial acetic acid. Both phthalanilic acids and imides have been characterised in detail and spectroscopic data are given. The kinetics of cyclisation for phthalanilic acids has been examined in detail, and it has emerged that a complex mechanism is operating. This initially involves a reversible, solvent assisted intramolecular nucleophilic attack by amide nitrogen on the carboxylic acid carbonyl. Clear evidence is seen for a long-lived intermediate as a precursor to imide formation. The observed kinetics are rationalised using a model of rapid pre-equilibration, followed by the slow breakdown of the intermediate to imide. Observed rate constants for pre-equilibration show a well behaved, linear Hammett plot (ρ = -1.1), whereas those for formation of imide do not.

Effect of cyclodextrin on the intramolecular catalysis of amide hydrolysis

The hydrolysis reaction of phthalamic acids (HOOCArCONHR, R = p-NO2Ph 1a, Ph 1b, adamantyl 1c) and N-phenyl maleamic acid 2b was studied in the presence of hydroxypropyl-β-cyclodextrin (HPCD) in acid solution. The reactions of 1a and 1b were studied also in the presence of β-cyclodextrin (β-CD). All the compounds formed inclusion complexes with HPCD, and the association constant was determined from the change in absorption of the substrate when the host is added in the case of 1a (90 M-1) and 2b (49 M-1). For 1c (4 × 104 M-1) a competition method was used, and for 1b the association equilibrium constant was obtained from the kinetic data (37 M-1) because it is too reactive for the spectrophotometric method. Both cyclodextrins strongly inhibited the reactions, and analysis of the kinetic data for HPCD indicated that the reactions of complexed 1a, 1b, and 2b are at least 10-30 times slower than in the bulk solution whereas 1c reacts only 4.6 times slower when it is complexed. The inhibition is attributed to changes in the geometry of the substrate due to interaction of the carboxylic group and/or the amide with the OH at the rim of the cyclodextrin. The differences in the relative effect observed for 1c are attributed to the formation of a tighter complex with this substrate.

Cyclodextrin effect on intramolecular catalysis

HPCD inhibits the hydrolysis reaction of monoamides and monoesters of phthalic and maleic acid at pH 2. The magnitude of inhibition depends on the leaving group. For some of the substrates, the reaction in the cavity is more than 100 times slower than that in solution.