2-Chloro-4-nitrobenzoic acid

• CAS: 99-60-5
• Catalog Number: ACM99605
• Category: Main Products
• Molecular Weight: 201.56
• Molecular Formula: C₇H₄ClNO₄
• Synonyms: EINECS 202-771-0; Benzoic acid,2-chloro-4-nitro; 4-nitro-2-chlorobenzoic acid; 2-Chlor-4-nitro-benzoesaeure; 2-chloro-para-nitrobenzoic acid; Kyselina 2-chloro-4-nitrobenzoova; 2-chloro-4-nitro-benzoic acid
• IUPAC Name: 2-Chloro-4-nitrobenzoic acid
• Boiling Point: 362.2ºC at 760 mmHg
• Melting Point: 139-143ºC
• Flash Point: 172.8ºC
• Density: 1.602 g/cm³
• Appearance: light yellow powder
• Exact Mass: 200.98300
• Hazard Statements: Xi:Irritant
• Safety Description: S26-S36
• Stability: Stable under normal temperatures and pressures.
• WGK Germany: 3

Case Study

Study of polymorphisms in 2-chloro-4-nitrobenzoic acid

Barsky, Inna, et al. New Journal of Chemistry 32.10 (2008): 1747-1753.

The solid-state behavior of 2-chloro-4-nitrobenzoic acid has been re-examined. Infrared spectroscopy, differential scanning calorimetry (DSC), and thermal microscopy studies, as well as X-ray powder patterns of two polymorphs, are described. Modification II is the thermodynamically stable crystal morphology from absolute zero to its transition point, which, according to DSC analysis, occurs at approximately 97°C. Above this temperature, the material transforms into Modification I, with lattice parameters undergoing a dramatic evolution with increasing temperature. Synchrotron radiation powder diffraction measurements confirmed the existence of two polymorphs. Both modifications were structurally characterized by single-crystal X-ray diffraction.
2-Chloro-4-nitrobenzoic acid powder was described as the Type I modified by FT-IR spectroscopy. FT-IR measurements were performed using a spectrometer on a KBr disk. The material was recrystallized at room temperature from various solvents. All crystallization conditions, except for water as a solvent, resulted in the formation of Modification II. Aqueous solutions led to the simultaneous crystallization of both polymorphs.

A novel pathway for the degradation of 2-chloro-4-nitrobenzoic acid

Prakash, Dhan, et al. Applied and environmental microbiology 77.18 (2011): 6606-6613.

Acinetobacter RKJ12 is able to utilize 2-chloro-4-nitrobenzoic acid (2C4NBA) as its sole source of carbon, nitrogen, and energy. During the degradation of 2C4NBA by the RKJ12 strain, multiple metabolites were isolated and identified using a combination of chromatography, spectroscopy, and enzyme activity analysis, revealing a novel assimilation pathway involving both oxidative and reductive decomposition mechanisms. The metabolism of 2C4NBA is initiated by oxidative adjacency dehalogenation to form 2-hydroxy-4-nitrobenzoic acid (2H4NBA), which is then metabolized by monooxygenase to 2,4-dihydroxybenzoic acid (2,4DHBA), releasing chloride and nitrite ions simultaneously.
RKJ12 cells were aerobically cultured in mineral salt medium (MSM) (34) supplemented with a final concentration of 20 mM 2-chloro-4-nitrobenzoic acid (2C4NBA). When necessary, 10 mM sodium succinate (SS) was used to assist microbial growth. Due to the low water solubility of 2C4NBA, 2C4NBA was incubated with MSM (pH 7.2) at 30°C with a shaking speed of 150 rpm for 24 hours. Mineral salt media containing dissolved 2C4NBA (20 mM) was filtered before inoculation to determine the kinetics of 2C4NBA degradation under aeration at 30°C. Bacterial growth was determined by spectrophotometric monitoring of optical density at 600 nm (OD). To investigate the ability of the RKJ12 strain to utilize pathway intermediates, cells were cultured in MSM under the same conditions with a single carbon source containing multiple metabolites (10 to 20 mM).

Characterization and molecular modeling of 2-chloro-4-nitrobenzoic acid

Lemmerer, Andreas, Catharine Esterhuysen, and Joel Bernstein. Journal of pharmaceutical sciences 99.9 (2010): 4054-4071.

The active pharmaceutical ingredient, 2-chloro-4-nitrobenzoic acid (2C4N), is a potential novel therapy as an antiviral and anticancer drug, existing in a solid state. The possibility of preparing a cocrystal with the GRAS compound nicotinamide (nic) was investigated using a thermal contact method. A 1:1 cocrystal was prepared via liquid-assisted milling and solution crystallization experiments. The determination of the crystal structure revealed that the two molecules are linked by carboxylic acid-pyridine hydrogen bonds. The melting point of the cocrystal was higher than that of either pure ingredient, indicating that the drug cocrystal exhibits superior thermal stability compared to the pure drug compound. Molecular modeling calculations further support the relative stability of the interactions in the cocrystal compared to the pure compound.
0.100 g of nicotine (0.819 mmol) and 0.165 g of 2-chloro-4-nitrobenzoic acid (0.819 mmol) were dissolved in 6 mL of hot methanol and stirred for 1 h until completely dissolved. After filtration, the solution was left uncapped and allowed to evaporate slowly at room temperature. This yielded pale yellow bicrystalline compounds with a thick, plate-like morphology. 0.100 g of nicotine (0.819 mmol) and 0.165 g of 2-chloro-4-nitrobenzoic acid (0.819 mmol) were ground together in a solvent-free pestle and mortar for 20 minutes. A similar formulation was also ground, with a few drops of methanol added, and soaked for 20 minutes. The eutectic was prepared by first melting the higher-melting-point 2-chloro-4-nitrobenzoic acid on a thermal microscope slide, covering it with a glass slide, and cooling to form a thin crystalline film. The lower layer of molten nicotine was then melted on the same slide, and through capillary action, the liquid was drawn into the solid 2-chloro-4-nitrobenzoic acid and slid over it, while the microscope slide was rapidly cooled. A thin eutectic film was prepared at the interface between the two compounds.

A study the polycrystalline phase transformation of 2-chloro-4-nitrobenzoic acid

Aitipamula, Srinivasulu, Pui Shan Chow, and Reginald BH Tan. CrystEngComm 13.3 (2011): 1037-1045.

Using a variety of analytical techniques, including powder X-ray diffraction, single-crystal X-ray diffraction, differential scanning calorimetry, and thermogravimetric analysis, a previously unknown monohydrate and five anti-HIV solvents-2-chloro-4-nitrobenzoic acid (CNBA)-were discovered. The solvents are readily available from 1,4-dioxane, dimethylsulfite, acetylbenzophenone, p-xylene, and acetylenes. In the crystal structures of three solvents (1,4-dioxane, p-xylene, and acetylenes), CNBA molecules form acid-acid dimer motifs, which are stabilized by p/p stacking interactions. Slurry experiments confirmed the thermodynamic stability of Form I at room temperature. Milling experiments using various solvents with catalytic amounts showed that, in most cases, Form II transforms into Form I, and both forms convert to hydrates upon milling with water. During grinding with 1,4-dioxane and meta-yne, a solvent was generated. After a prolonged grinding period of 60 minutes, the solvent transformed into the more stable type I.
200 mg of 2-chloro-4-nitrobenzoic acid was used in the experiment. Liquid-assisted grinding or solvent drop grinding experiments were conducted by adding approximately 0.05 mL of a selected solvent to the reactants before grinding. A total of 12 solvents were selected, including water, acetone, ethyl acetate, ethanol, diethyl ether, n-hexane, chloroform, 1,4-dioxane, DMSO, acetylbenzophenone, p-xylene, and methylyne. The resulting powder samples were analyzed by PXRD. The external temperature of the grinding jar did not exceed approximately 30 degrees Celsius after the experiment.

Custom Q&A

What is the molecular formula of 2-Chloro-4-nitrobenzoic acid?

The molecular formula is C7H4ClNO4.

What is the molecular weight of 2-Chloro-4-nitrobenzoic acid?

The molecular weight is 201.56 g/mol.

What is the IUPAC name of 2-Chloro-4-nitrobenzoic acid?

The IUPAC name is 2-chloro-4-nitrobenzoic acid.

What is the InChI of 2-Chloro-4-nitrobenzoic acid?

The InChI is InChI=1S/C7H4ClNO4/c8-6-3-4(9(12)13)1-2-5(6)7(10)11/h1-3H,(H,10,11).

What is the InChIKey of 2-Chloro-4-nitrobenzoic acid?

The InChIKey is QAYNSPOKTRVZRC-UHFFFAOYSA-N.

What is the Canonical SMILES of 2-Chloro-4-nitrobenzoic acid?

The Canonical SMILES is C1=CC(=C(C=C1[N+](=O)[O-])Cl)C(=O)O.

What is the CAS number of 2-Chloro-4-nitrobenzoic acid?

The CAS number is 99-60-5.

What is the European Community (EC) number of 2-Chloro-4-nitrobenzoic acid?

The European Community (EC) number is 202-771-0.

How many hydrogen bond acceptor counts are there in 2-Chloro-4-nitrobenzoic acid?

There are 4 hydrogen bond acceptor counts in 2-Chloro-4-nitrobenzoic acid.

Is 2-Chloro-4-nitrobenzoic acid a canonicalized compound?

Yes, 2-Chloro-4-nitrobenzoic acid is a canonicalized compound.