159246-81-8

Basic information

• Product Name: Benzoic acid, 4-amino-, radical ion(1+) (9CI)
• Synonyms: Benzoic acid, 4-amino-, radical ion(1+) (9CI)
• CAS NO: 159246-81-8
• Molecular Formula: C7H7NO2
• Molecular Weight: 137.14
• Mol File: 159246-81-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzoic acid, 4-amino-, radical ion(1+) (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-amino-, radical ion(1+) (9CI)(159246-81-8)
• EPA Substance Registry System: Benzoic acid, 4-amino-, radical ion(1+) (9CI)(159246-81-8)

Safety Data

• Hazardous Substances Data: 159246-81-8(Hazardous Substances Data)

Upstream product

• 92-36-4 2-(4-aminophenyl)-6-methyl-1,3-benzothiazole 
• 586-76-5 4-Bromobenzoic acid 
• 141-43-5 ethanolamine 
• 62-23-7 4-nitro-benzoic acid 
• 619-80-7 4-nitrobenzamide 
• 4380-38-5 4-(4-methoxy-benzylidenamino)-benzoic acid 
• 107692-58-0 4-Amino-benzoic acid 2-oxo-2-phenyl-ethyl ester 
• 97279-81-7 trans-4-amino-3-hydroxy-1,5-cyclohexadiene-1-carboxylic acid 
• 108133-61-5 4-{[1-(3-Chloro-phenyl)-meth-(E)-ylidene]-amino}-benzoic acid 
• 4074-08-2 4-{[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-amino}-benzoic acid 
• 108133-58-0 4-{[1-(4-Formyl-phenyl)-meth-(E)-ylidene]-amino}-benzoic acid 
• 97293-82-8 (3R,4R)-4-Amino-3-(1-carboxy-vinyloxy)-cyclohexa-1,5-dienecarboxylic acid; compound with trifluoro-acetic acid 
• 5351-17-7 4-aminobenzohydrazide 
• 873-74-5 4-Aminobenzonitrile 

Downstream Products

• 117099-20-4 4-[2-(tetra-O-acetyl-β-D-glucopyranosyloxy)-benzylidenamino]-benzoic acid 
• 121623-80-1 9-(3t-carboxy-acryloyloximethyl)-4-[(4-carboxy-phenylimino)-methyl]-3,8-dihydroxy-1,6-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepin-7-carboxylic acid 
• 117821-34-8 4-((2-hydroxyethyl)amino)benzoic acid 
• 6275-82-7 4-((cyanomethyl)amino)benzoic acid 
• 1234-27-1 4,4'-(carbonylbis(azanediyl))dibenzoic acid 
• 4385-62-0 4-(pyridin-2-yl)benzoic acid 
• 5432-04-2 4-(3-carboxy-acryloylamino)-benzoic acid 
• 102451-12-7 4-[(6-methyl-[2]pyridylmethylen)-amino]-benzoic acid 
• 582-80-9 p-benzamidobenzoic acid 
• 109098-54-6 4-(4-oxopentanoylamino)benzoic acid 
• 71937-10-5 4-benzo[1,3]dioxol-5-ylmethyleneamino-benzoic acid 
• 119-24-4 pteroic acid 
• 21315-27-5 4-[(4-oxo-4H-chromen-2-yl)carbonylamino]benzoic acid 
• 93898-79-4 4-[(4-amino-2-methylsulfanyl-pteridin-6-ylmethyl)-amino]-benzoic acid 

Relevant articles and documents

Discovery and recovery of delta p-aminobenzoic acid

We explore the polymorphism of p-aminobenzoic acid (pABA) under high-pressure conditions. We have been able to isolate a new high-pressure form (δ-pABA) at pressures exceeding 0.3 GPa from three different pressure-transmitting media, water, water?:?ethanol and pure ethanol. We explore the compression behaviour of α-pABA in each of these media using neutron powder diffraction and observe that the transition is kinetically hindered using the aqueous ethanol and ethanol solutions compared with the pure aqueous medium. δ-pABA is sufficiently stable to be recovered to ambient pressure to enable its characterisation via X-ray powder diffraction and differential scanning calorimetry. At ambient pressure we have observed that δ-pABA converts into α-pABA on heating beyond 70 °C.

Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.

Switching on prodrugs using radiotherapy

Chemotherapy is a powerful tool in the armoury against cancer, but it is fraught with problems due to its global systemic toxicity. Here we report the proof of concept of a chemistry-based strategy, whereby gamma/X-ray irradiation mediates the activation of a cancer prodrug, thereby enabling simultaneous chemo-radiotherapy with radiotherapy locally activating a prodrug. In an initial demonstration, we show the activation of a fluorescent probe using this approach. Expanding on this, we show how sulfonyl azide- and phenyl azide-caged prodrugs of pazopanib and doxorubicin can be liberated using clinically relevant doses of ionizing radiation. This strategy is different to conventional chemo-radiotherapy radiation, where chemo-sensitization of the cancer takes place so that subsequent radiotherapy is more effective. This approach could enable site-directed chemotherapy, rather than systemic chemotherapy, with ‘real time’ drug decaging at the tumour site. As such, it opens up a new era in targeted and directed chemotherapy. [Figure not available: see fulltext.].

Rhodium nanoparticles supported on 2-(aminomethyl)phenols-modified Fe3O4 spheres as a magnetically recoverable catalyst for reduction of nitroarenes and the degradation of dyes in water

A magnetic nanostructured catalyst (Fe3O4@SiO2-Amp-Rh) modified with 2-(aminomethyl)phenols (Amp) was designed and prepared, which is used to catalyze the reduction of aromatic nitro compounds into corresponding amines and the degradation of dyes. The 2-aminomethylphenol motif plays a vital role in the immobilization of rhodium nanoparticles to offer extraordinary stability, which has been characterized by using various techniques, including transmission electron microscopy (TEM), thermal gravimetric analyzer (TGA), X-Ray Diffraction (XRD), and X-ray photoelectron spectroscopy (XPS). A variety of nitroaromatic derivatives have been reduced to the corresponding anilines in water with up to yields of 99% within 1?h at room temperature. In addition, the catalyst system is effective in catalyzing the reduction of toxic pollutant 4-nitrophenol and the degradation of MO, MB and RhB dyes. Importantly, this catalyst Fe3O4@SiO2-Amp-Rh can be easily recovered by an external magnetic field because of the presence of magnetic core of Fe3O4, and the activity of Fe3O4@SiO2-Amp-Rh does not decrease significantly after 7 times’ recycling, which indicates that the catalyst performed high reactivity as well as stability. Graphical abstract: [Figure not available: see fulltext.]

UiO-66/btb/Pd as a stable catalyst reduction of 4-nitrophenol into 4-aminophenol

In order to synthesize highly sparse nanoparticles, UiO-66-NH2 can be utilized as an appropriate support. It has great surface area, which is functionalized by 1,3-bis(dimethylthiocarbamoyloxy)benzene compounds that can act as the powerful performers, hence, the Pd (II) is a complex without aggregate over the UiO-66-NH2 microspheres structures (UiO-66/btb/Pd). Nitro-aromatic pollution in industrial waste streams threat wellbeing of water resources. The produced UiO-66/btb/Pd nanocatalyst showed appropriate catalytic activity for reduce nitro-aromatic compounds in aqueous solution. XRD, EDS, SEM, FT-IR, and TEM were utilized for characterizing the nanostructures UiO-66/btb/Pd.

Magnetically‐recoverable Schiff base complex of Pd(II) immobilized on Fe3O4@SiO2 nanoparticles: an efficient catalyst for the reduction of aromatic nitro compounds to aniline derivatives

Fe3O4@SiO2/Schiff base/Pd(II) is reported as a magnetically recoverable heterogeneous catalyst for the chemoselective reduction of aromatic nitro compounds to the corresponding amines through catalytic transfer hydrogenation (CTH). In this regard, a small amount of the nanocatalyst (0.52?mol% Pd) and hydrazine hydrate, showing safe characteristics and perfect ability as the hydrogen donor, were added to the nitro substrates. The experiments described the successful reduction of aromatic nitro compounds with good to excellent yields and short reaction times. The catalyst, due to its magnetic property, could be simply separated from the reaction mixture by a permanent magnet and reused in seven consecutive reactions without considerable loss in its activity. Moreover, the leaching of Pd was only 3.6% after the seventh run. Thus, the most striking feature of this method is to use a small amount of the magnetic nanocatalyst along with a cheap and safe hydrogen source to produce the important amine substances selectively, which makes the method economical, cheap, environmentally friendly, and simple. Graphic abstract: [Figure not available: see fulltext.]

Highly porous copper-supported magnetic nanocatalysts: made of volcanic pumice textured by cellulose and applied for the reduction of nitrobenzene derivatives

Herein, a novel designed heterogeneous catalytic system constructed of volcanic pumice magnetic particles (VPMPs), cellulose (CLS) as a natural polymeric matrix, and copper nanoparticles (Cu NPs) is presented. Also, to enhance the inherent magnetic property of VPMP, iron oxide (Fe3O4) nanoparticles have been prepared and incorporated in the structureviaanin situprocess. As its first and foremost excellent property, the designed composite is in great accordance with green chemistry principles because it contains natural ingredients. Another brilliant point in the architecture of the designed composite is the noticeable porosity of VPMP as the core of the composite structure (surface area: 84.473 m2g?1). This great porosity leads to the use of a small amount (0.05 g) of the particles for catalytic purposes. However, the main characterization methods, such as Fourier-transform infrared and energy-dispersive X-ray spectroscopy, thermogravimetric analysis, and electron microscopy, revealed that the spherical metallic particles (Fe and Cu oxides) were successfully distributed onto the surface of the VPMP and CLS matrices. Further, vibrating-sample magnetometer analysis confirmed the enhancement of the magnetic property (1.5 emu g?1) of the composite through the addition of Fe3O4nanoparticles. Further, the prepared (Fe3O4@VPMP/CLS-Cu) nanocomposite has been applied to facilitate the reduction reaction of hazardous nitrobenzene derivatives (NBDs) to their aniline analogs, with 98% conversion efficiency in eight minutes under mild conditions. Moreover, the good reusability of the catalytic system has been verified after recycling it ten times without any significant decrease in the performance.

Synthesis of CoFe2O4@Pd/Activated carbon nanocomposite as a recoverable catalyst for the reduction of nitroarenes in water

Efficient reduction of nitro compounds into amines is an important industrial transformation. So, it is a great deal to design new catalysts for efficient reduction of the nitro compounds especially in water. In this work, a new magnetic Pd/activated carbon nanocomposite (CoFe2O4@Pd/AC) was synthesized via metal-impregnation-pyrolysis method. The CoFe2O4@Pd/AC was fully characterized by FT-IR, PXRD, FESEM, TEM, VSM, EDX-mapping and BET techniques. The results showed that CoFe2O4@Pd/AC is a highly reactive and easily recoverable magnetic catalyst for the reduction of the nitro compounds by using NaBH4 in water. For instance, aniline was obtained in high yield (99%) after 75 ?min at 25 ?C by using just 6 ?mg of the catalyst. In addition, CoFe2O4@Pd/AC was recovered by a simple magnetic decantation and it exhibits stable activity and remains intact during the catalytic process with no significant loss in activity (8 cycles).

A highly effective green catalyst Ni/Cu bimetallic nanoparticles supported by dendritic ligand for chemoselective oxidation and reduction reaction

The highly active Ni/Cu bimetallic nanoparticles (NPs) of the different molar ratios of Ni and Cu (1:1, 1:3, 3:1) assisted by dendritic ligand 2,4,6-Tris (di-4-chlorobenzamido)-1,3-diazine were synthesized successfully confirmed by Scanning Electron Microscopy (SEM), Electron Diffraction X-ray (EDX), X-ray fluorescence spectroscopy (XRF), X-ray diffraction (XRD), and Transmission Electron Microscopy (TEM) analysis. These NPs were studied as a heterogeneous catalyst for the chemoselective oxidation of alcohol to the corresponding aldehyde at 30?min and chemoselective reduction of aromatic nitro substituents to the corresponding amino substituents at 20?min, while the Ni/Cu (3:1) NPs were found to be the most effective among other Ni/Cu?(1:1)?and Ni/Cu?(1:3)?NPs at room temperature under mild conditions. The Ni/Cu (3:1) NPs can be recycled for at least five successive runs with no perceptible decrease in catalytic activity. Graphic abstract: [Figure not available: see fulltext.]

Hydrophilic nickel phosphate nanoparticles: An efficient catalyst for the hydrogenation of nitroarenes

A clean and highly efficient chemical method was developed for the synthesis of hydrophilic nickel phosphate nanoparticles and the formation of nanoparticles was confirmed by discrete spectral techniques. The synthesized nanoparticles were found to be an