Shaanxi BLOOM Tech Co., Ltd. is one of the most experienced manufacturers and suppliers of 2-nitrobenzoic acid cas 552-16-9 in China. Welcome to wholesale bulk high quality 2-nitrobenzoic acid cas 552-16-9 for sale here from our factory. Good service and reasonable price are available.
2-Nitrobenzoic acid, CAS552-16-9, Molecular formula C7H5NO4. Yellow white crystal. Slightly soluble in water, soluble in ethanol and ether. Organic solvents. Flammable when exposed to open flames or high temperatures. High thermal decomposition releases toxic nitrogen oxides. During the reduction process, ortho aminobenzoic acid is generated. This product is flammable and irritating. Flammable when exposed to open flames or high temperatures. Under high thermal decomposition, toxic nitrogen oxides are produced. Its chemical properties are flammable, and when exposed to high heat, it decomposes to produce toxic nitrogen oxides, which are produced through the oxidation of ortho nitrotoluene in industrial production. Mainly used in the fields of dye intermediates and organic synthesis. This substance is mutagenic to microorganisms and DNA repair systems, can pollute water bodies and the atmosphere, and may disrupt ecosystem balance after acidification. Wear protective equipment during operation, keep away from oxidants and alkaline substances during storage, and equip emergency facilities for leaks. Used for dye intermediates and organic synthesis. It is obtained through the oxidation of ortho nitrotoluene.
|
Chemical Formula |
C7H5NO4 |
|
Exact Mass |
167 |
|
Molecular Weight |
167 |
|
m/z |
167 (100.0%), 168 (7.6%) |
|
Elemental Analysis |
C, 50.31; H, 3.02; N, 8.38; O, 38.29 |
|
|
|
It is an organic compound whose reaction properties are as follows:
Carry out acid-base neutralization reaction to generate corresponding salts.
It can be reduced to 2-aminobenzoic acid by reducing agents (such as sodium bisulfite, zinc, etc.).
It can undergo amidation reaction with amines to generate corresponding amides.
It can react with diethyl carbonate and dehydrating agent (such as diethyl malonate) to produce diethyl 2-oxobenzoate.
Coupling reaction with aromatic aldehydes or aromatic amines to generate new diaryl urea compounds.
It can be nitrated by nitrating agent to generate 2,4-dinitrobenzoic acid.
Oxidation reaction with cuprous bromide, ozone, etc., to generate corresponding oxidation products.
In general, the reaction properties of there are relatively diverse, and it can participate in many organic chemical reactions.
2-Nitro-benzoica, also known as 2-nitrobenzoic acid, is a yellow white crystal with a melting point of 146-148 ℃. It is slightly soluble in water but easily soluble in organic solvents such as ethanol, ether, and acetone. Its molecular structure contains both nitro (- NO ₂) and carboxyl (- COOH) groups, endowing it with unique chemical properties: the strong electron withdrawing effect of nitro groups enhances the acidity of carboxyl groups (pKa value 2.16), making it excellent in pH sensitive reactions; The activity of carboxyl groups makes them important intermediates in organic synthesis.
1. Intermediate of antibiotics and anti-inflammatory drugs
2-Nitro-benzoica is a key intermediate for the synthesis of β - lactam antibiotics, such as cephalosporins. Its carboxyl group can undergo condensation reaction with the penicillin core to form stable amide bonds, while the nitro group can be converted into an amino group through reduction reaction, further participating in the construction of drug molecules. For example, in the synthesis of third-generation cephalosporin cefotaxime sodium, intermediates derived from 2-nitro-benzoica can protect the β - lactam ring from hydrolysis, significantly improving drug stability.
2. Raw materials for antipsychotic drugs
Ortho 2-nitro-benzoica is an important precursor of 5-hydroxytryptamine 2 (5HT2) and dopamine D2 receptor antagonists. Taking Xiweilai Si Na (the world's first drug for treating acute lung injury) as an example, in its synthetic pathway, 2-nitro-benzoica first reacts with dichlorosulfoxide to form o-nitrobenzoyl chloride, which is then condensed with glycine benzyl ester p-toluenesulfonic acid salt.
Finally, the target product is obtained through reduction, sulfonylation and other steps. This drug effectively reduces the mortality rate of patients with acute respiratory distress syndrome (ARDS) by inhibiting neutrophil elastase.
3. Research and development of anti-tumor drugs
The nitro group of 2-nitro-benzoica can be reduced to an amino group, forming ortho aminobenzoic acid, which is a key intermediate for the synthesis of folate antagonists such as methotrexate. In addition, its carboxyl group can form complexes with platinum compounds such as cisplatin, enhancing the drug's targeting of tumor cells. Research has shown that platinum complexes modified with 2-nitro-benzoica exhibit a 30% higher inhibition rate on lung cancer cell line A549 compared to traditional cisplatin in vitro experiments.
1. Azo dye intermediates
2-Nitro-benzoica is the core raw material for synthesizing azo dyes such as Acid Orange II and Direct Black 38. Its nitro group can be reduced to an amino group, which reacts with diazonium reagents (such as sodium nitrite) to form diazonium salts, which are then coupled with aromatic amines or phenols to form azo dyes with bright colors and excellent fastness. For example, in the synthesis of Acid Orange II, ortho nitrobenzoic acid undergoes a three-step reaction of reduction, diazotization, and coupling to obtain orange red dye, which is widely used in the dyeing of wool and silk.
2. Fluorescent dyes and markers
The carboxyl group of ortho nitrobenzoic acid can be linked to fluorescent groups such as rhodamine B and fluorescein through esterification or amidation reactions, forming fluorescent markers with specific wavelengths.
For example, by reacting o-nitrobenzoic acid with isothiocyanate of Rhodamine B, a red fluorescent probe for cell imaging can be prepared with a quantum yield of 0.85, significantly higher than traditional dyes.
3. Metal indicators and complexing agents
The carboxyl and nitro groups of ortho 2-nitrobenzoic acid can form stable complexes with metal ions such as Cu ² ⁺ and Fe ³ ⁺, which are used for colorimetric determination of metal content. For example, in a pH 5 buffer solution, 2-nitro-benzoica forms a 1:1 complex with Cu ² ⁺, with a maximum absorption wavelength of 520nm and a detection limit as low as 0.01 μ g/mL. It is widely used for rapid detection of heavy metals in environmental water samples.
1. Polymer material modifier
2-Nitro-benzoica can be used as a chain extender or crosslinking agent for polymer materials such as polyester and polyamide. Its carboxyl group can react with the terminal hydroxyl group of polyester, extending the molecular chain and improving the material strength. For example, when synthesizing polyethylene terephthalate (PET), adding 0.5% ortho nitrobenzoic acid can increase the tensile strength of PET from 50MPa to 65MPa, while reducing melt viscosity and improving processing performance.
2. Rare earth complex luminescent materials
The carboxyl group of 2-nitro-benzoica can form stable complexes with rare earth ions (such as Nd ³ ⁺, Eu ³ ⁺), exhibiting unique photoluminescence properties.
For example, by reacting 2-nitro-benzoica with neodymium nitrate in an ethanol water mixed solvent, light purple crystals [Nd (o-NO ₂ - C ₆ H ₄ COO) ∝ (DMF) ₂] ₂ can be prepared. The complex emits strong red fluorescence (λ max=612nm) under UV excitation, with a quantum yield of 12%, and can be used to prepare OLED display materials.
3. Preservatives and antioxidants
The nitro group of ortho 2-nitro-benzoica has strong oxidizing properties and can inhibit microbial growth, while its carboxyl group can chelate with metal ions to prevent oxidation reactions. For example, adding 0.1% 2-nitro-benzoica to lubricating oil can reduce the corrosion rate of copper sheets by 80%, while extending the oxidation induction period of the oil from 120 minutes to 240 minutes, significantly improving the stability of the lubricating oil.
1. Environmental pollutant indicator
2-Nitro-benzoica can serve as an indicator for nitrogen oxides (NOs) in the atmosphere. Its nitro group can be oxidized by NO ₓ to form a nitroquinone structure, causing the solution color to change from yellow to dark red. The concentration of NO ₓ can be quantitatively determined by colorimetric method. For example, filling the air sampling tube with ortho 2-nitro-benzoica silica gel composite material can monitor the concentration of NO ₓ in industrial areas in real time, with a detection range of 0.1-10ppm and a response time of less than 5 minutes.
2. Adsorbents for wastewater treatment
Activated carbon (AC) modified with ortho 2-nitro-benzoica has high selective adsorption capacity for heavy metal ions such as Pb ² ⁺ and Cd ² ⁺.
For example, by reacting 2-nitro-benzoica with chloroacetic acid to produce carboxymethylation products, which are then loaded onto the surface of activated carbon, the modified AC prepared has an adsorption capacity of 120mg/g for Pb ² ⁺, which is three times that of unmodified AC. It can stably adsorb within the pH range of 2-10 and is suitable for the treatment of acidic mine wastewater.
3. Acid rain formation simulator
2-Nitro-benzoica, as a representative organic acid, can be used to simulate the impact of acid rain on ecosystems. Research has shown that when pH<4.5, ortho 2-nitro-benzoica can dissolve aluminum ions (Al ³ ⁺) in soil, causing an increase in Al ³ ⁺ concentration in water to 0.5mg/L, which is toxic to fish gill tissue and leads to respiratory failure. This model provides an important theoretical basis for acid rain control.
1. Organic synthesis raw materials
2-Nitrobenzoic acid is a common organic synthesis raw material that can be used to synthesize o-nitrobenzaldehyde. O-nitrobenzaldehyde is an important intermediate in the synthesis of the anti angina drug nitropyridine. After reducing the nitro group to an amino group, it becomes o-aminobenzaldehyde, which is an intermediate in the synthesis of quinoline ring drugs. Using 2-nitro-benzoica as the raw material, o-nitrobenzaldehyde is obtained through imidazoline reduction hydrolysis. The process is simple and the conditions are mild. The synthesis route is shown in the following figure.
2. Raw materials for drug synthesis
2-Nitro-benzoica can be used to synthesize sivelestat sodium. sivelestat sodium is the first drug in the world to treat acute lung injury with systemic inflammatory response syndrome. It is a Elastin inhibitor, which can selectively inhibit the release of Elastase from neutrophils and treat acute lung injury. The reaction path for the synthesis of siverex sodium from o-nitrobenzoic acid is shown in the following figure.
Using glycine benzyl ester p-toluenesulfonate, p-hydroxybenzenesulfonic acid, tervaloyl chloride, and 2-nitro-benzoica as the main raw materials, o-nitrobenzoyl chloride was first synthesized by reacting 2-nitro-benzoica with dichlorosulfoxide. Then, o-nitrobenzoyl glycine benzyl ester was prepared together with glycine benzyl ester p-toluenesulfonate. After amino reduction, o-aminobenzoamide glycine benzyl ester was obtained, Then, N - [O - (p-tervaloyloxybenzenesulfonamido) benzoyl] glycine benzyl ester is obtained by reacting with p-tervaloyloxybenzenesulfonyl chloride obtained from p-hydroxybenzenesulfonic acid. After reduction and alkalization, Sivelex sodium is obtained.
3. Ligand molecules used as rare earth complexes
The carboxylic acid in orthonitrobenzoic acid can form complexes with rare earth elements, which have many special structures and luminescent properties, and can be used for extraction separation, fungicides, luminescence, and functional materials. Dissolve 2-nitro-benzoica and neodymium nitrate in ethanol water mixed solvent respectively, add ammonia water to adjust pH after mixing to obtain lavender precipitation, add the precipitation into DMF solution, and obtain [Nd (o-NO2-C6H4COO) 3 (DMF) 2] 2 crystal after 3 days. Its molecular structure is shown in the following figure.
The neodymium complex [Nd (o-NO2-C6H4COO) 3 (DMF) 2] 2 crystal belongs to a triclinic system. Each Nd (III) is bridged by four o-nitrobenzoate radicals, with a coordination number of 8. The coordination atoms come from six oxygen atoms of five o-nitrobenzoate carboxylates and two carbonyl oxygen atoms of DMF, respectively. The hydrogen bonding and π - π stacking interactions in the complex make it a three-dimensional structure. The complex also exhibits photoluminescence and excellent fluorescence properties. The luminescence intensity of Nd (III) ions is relatively weak, and strong fluorescence can only be generated when a complex is formed and excited by ultraviolet light. Its luminescent performance mainly comes from the ortho 2-nitro-benzoica ligand in the crystal, which has a rigid structure and contains atoms such as nitrogen and oxygen, making it an ideal luminescent structure.
There are various methods for the synthesis of 2-nitrobenzoic acid, and the most common ones are listed below:
It is prepared by oxidation from ortho nitrotoluene as the starting material. In a high-pressure reactor, methanol solvent, o-nitrotoluene, and catalyst MnO4/RuO4 were added, and oxygen was introduced with sufficient stirring. The reaction was carried out at 100-150 ℃ and 0.1-2MPa for 5-15 hours. After the reaction was completed, it was cooled to room temperature, pressure was released, the catalyst was filtered, extracted with ether water, the organic phase was washed with water, and the solvent was distilled to recover 2-nitro-benzoica. The yield was 89.1%, and the purity was over 96%. The filtered catalyst can be reused. The reaction route is as follows.
Using o-nitrotoluene as the raw material, acetonitrile, DMF, ethanol, or ethanol aqueous solution containing 10% to 95% volume of ethanol as the solvent, a metal porphyrin with the structure shown in equations (I), (II), or (III) of the following figure was selected as the catalyst. In a 0.3-2 mol/L sodium hydroxide solution, oxygen of 0-0.8 MPa was introduced. Under microwave reaction temperature of 60-170 ℃ and microwave synthesis power of 0-85 W, 2-nitro-benzoica was synthesized for 2-60 minutes. Compared with ordinary methods, this method uses microwave synthesis of o-nitrobenzoic acid, which reduces the reaction pressure from the existing 0.8-3MPa to 0-0.8MPa. This not only reduces the energy consumption required for the reaction, but also greatly increases the safety of the reaction. In addition, this method reduces the reaction time from the existing 2-12 hours to 2-60 minutes, greatly shortening the reaction time and significantly reducing the synthesis cost.
Using o-nitrotoluene as the starting material and quaternary ammonium salt A-1 as the phase transfer catalyst, KMnO4 was catalyzed to oxidize o-nitrotoluene to synthesize o-nitrobenzoic acid. The suitable reaction conditions were: reaction temperature 95 ℃, time 3 hours, and the amount of quaternary ammonium salt A-1 was 5% of the reaction substrate ONT. The ratio of KmnO4 to ONT is 2.5:1. When the reaction system is neutral, the optimal oxidation effect is achieved, and the highest product yield reaches 95%.
Hot Tags: 2-nitrobenzoic acid cas 552-16-9, suppliers, manufacturers, factory, wholesale, buy, price, bulk, for sale, 2 5 Dihydroxybenzaldehyde, Synthetic Chemical, 3 methyl 4 piperidone, N N N Trimethylethylenediamine, 3 Phenyltoluene, 2 4 Quinolinediol