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3-Nitrobenzonitrile, is an organic compound with CAS 619-24-9 and molecular formula C7H4N2O2. It is a colorless to light yellow solid. There is a nitro group (NO2) and a nitrile group (CN) in the molecule, both of which affect its chemical properties. The presence of nitro groups gives it significant acidity, while nitrile groups give it a certain degree of nucleophilicity. Under certain specific conditions, it may appear slightly yellow or light brown. The density is usually slightly greater than 1, and the specific values may vary slightly due to changes in temperature and pressure. However, under normal laboratory conditions, its density can be considered as about 1.2 g/cm ³. It can be soluble in most organic solvents, such as acetone, chloroform, and ethyl acetate. However, its solubility in water is relatively low, which makes it less biologically active in water.
Relevant chemical properties of 3-nitroaniline are as follows
| C.F | C7H4N2O |
| E.M | 148 |
| M.W | 148 |
| E.A | C, 56.76; H, 2.72; N, 18.91; O, 21.60 |
| m/z | 148 (100.0%), 149 (7.6%) |
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EINECS number: 210-587-7, MDL number: MFCD00007194, melting point 114-117 ° C (lit.), boiling point 165 ° C (21 mmHg), density 0.33 g/cm3 (20 ℃), refractive index 1.5300 (estimate), flash point 165 ° C/21mm, storage conditions Store below+30 ° C, Very soluble in Ether, Crystal Powder or Needles in form, Yellow in color, BRN637674, InChIKeyRUSAWEHOUGCWOPG-UHFFFAOYSA-N
The direct nitration method of benzonitrile is a method for synthesizing 3-Nitrobenzonitril. The following are the detailed steps of this method and its reaction between benzonitrile and nitric acid:
CH3C ≡ N + HNO3 → CH3C(NO2)CN + H2O
Reaction between benzonitrile and sodium nitrite:
CH3C(NO2)CN + NaNO2 → C7H4N2O2 + NaCl + H2O
Step 1: Prepare raw materials
Firstly, prepare the required raw materials: benzonitrile and nitric acid. Benzonitrile is the target compound, while nitric acid is the oxidant used to oxidize benzonitrile into 3-Nitrobenzone itrile.
Step 2: Mix the raw materials
Mix benzonitrile and nitric acid in a certain proportion. Normally, the amount of nitric acid used is slightly excessive to ensure complete reaction. After mixing, transfer the mixture to the reaction vessel.
Step 3: Reaction
Heat the mixture to an appropriate temperature in the reaction vessel to initiate the reaction. During the heating process, it is necessary to maintain a stable temperature and continuously stir to ensure a uniform reaction.
Step 4: Purification
After the reaction is completed, cool the reaction solution to room temperature. Then, the reaction solution was purified by methods such as crystallization and filtration to obtain a high-purity 3-Nitrobenzoitrile.
Polymer materials are an indispensable part of modern industry and technology, and they have wide applications in many fields, such as construction, automotive, electronics, medical, etc. With the continuous development of technology, the demand for polymer materials is also increasing. Therefore, finding new synthesis methods to produce polymer materials with excellent performance has become an important research direction.
3-Nitrobenzonitrile is an organic compound with the molecular formula C7H4N2O2. It has two functional groups, nitro and cyano, thus possessing unique chemical properties. Nitro groups can generate positive charges on other functional groups in molecules, while cyanide groups can generate negative charges on other functional groups in molecules. The mutual attraction of positive and negative charges makes 3 Nitrobenzanitrile widely used in organic synthesis.
(1) Synthetic polymer electrolyte
Polymer electrolytes are a type of polymer material with broad application prospects, and they have important applications in many fields, such as batteries, capacitors, sensors, etc. It can be used as an important raw material for synthesizing polymer electrolytes. Through steps such as nitrification and reduction reactions, 3 Nitrobenzoitrile can be converted into certain monomers with specific functions, and then copolymerized with other monomers to obtain polymer electrolytes. These polymer electrolytes have excellent electrochemical performance and stability, and can be used to manufacture high-performance products such as batteries and capacitors.
(2) Synthetic polymer fluorescent materials
Polymer fluorescent materials are a type of polymer material with broad application prospects, which have important applications in many fields, such as displays, lighting, and biological imaging. It can be used as an important raw material for synthesizing polymer fluorescent materials. Through steps such as nitration and reduction reactions, 3 Nitrobenzoitrile can be converted into certain monomers with fluorescent properties, and then copolymerized with other monomers to obtain polymer fluorescent materials. These polymer fluorescent materials have excellent optical properties and stability, and can be used to manufacture high-performance displays and lighting products.
(3) Synthetic polymer functional materials
Polymer functional materials are a type of polymer material with special functions, which have important applications in many fields, such as separation, catalysis, sensing, etc. It can be used as an important raw material for synthesizing polymer functional materials. Through steps such as nitrification and reduction reactions, 3 Nitrobenzoitrile can be converted into certain monomers with specific functions, and then copolymerized with other monomers to obtain polymer functional materials. These polymer functional materials have excellent performance and stability, and can be used to manufacture high-performance separation membranes, catalysts, sensors and other products.
(4) Drug intermediates
Synthesis of antibacterial drugs
Nitrobenzonitrile can be introduced into the core skeleton of quinolone antibiotics (such as ciprofloxacin side chains) through reduction and cyclization reactions.
Reaction example: Condensation with piperazine ring to generate cyanide containing side chain intermediate, further modified to obtain antibacterial active ingredient.
Development of anti-tumor drugs
Introducing aromatic heterocycles through Suzuki coupling reaction to construct tyrosine kinase inhibitors (such as imatinib analogs).
Mechanism of action: The cyanide group acts as an electrophilic group, enhancing the binding affinity between the drug and the target protein.
Research on antiviral compounds
Participate in the synthesis of HIV protease inhibitors containing nitrobenzonitrile structures, utilizing the electron withdrawing effect of nitro groups to enhance drug efficacy.
(5) Construction of bioactive molecules
Enzyme inhibitory activity
3-Nitrobenzonitrile derivatives exhibit nanomolar inhibitory activity against acetylcholinesterase (AChE) and can be used in Alzheimer's disease drug research.
Synthesis of Fluorescent Probes
Cyan groups participate in the formation of strong electron withdrawing conjugated systems, constructing fluorescent probes for detecting metal ions (such as Cu²⁺).
Application in the field of pesticides
Insecticides
Intermediate of neonicotinoid insecticides
M-nitrobenzonitrile reacts with tetrahydropyrrolidine to form heterocyclic compounds containing cyanomethyl groups, which exhibit insect nicotinic acetylcholine receptor agonist activity.
Pyrethroid synergist
Introducing nitrobenzene nitrile structure to enhance the photostability of pyrethroid insecticides and prolong their field efficacy.
Fungicide
Succinate dehydrogenase inhibitor (SDHI)
The synthesis of SDHI fungicides containing triazole structures through multi-step reactions of m-nitrobenzonitrile has shown significant efficacy in controlling powdery mildew and rust.
Benzimidazole precursor
Cyan groups participate in the formation of benzimidazole rings, and the resulting compounds exhibit contact killing activity against gray mold.
ALS enzyme inhibitor
Nitrobenzonitrile derivatives can be developed as highly efficient herbicides for wheat fields as inhibitors of acetyl lactate synthase.
Organic synthesis applications
Construction of heterocyclic compounds
Synthesis of Pyridine/Quinoline
Condensation with diethyl malonate, followed by cyclization dehydrogenation to generate 2-cyanopyridine; Synthesis of Quinoline-4-carbonitrile via Friedl ä nder Reaction.
Indole skeleton construction
Under palladium catalysis, Sonogashira coupling occurs with terminal alkynes, followed by cyclization to obtain 3-cyanoindole derivatives.
Nitrogen-containing compound modification
Synthesis of amidine compounds
Cyan groups are hydrolyzed into amides, which are then condensed with amines to form amidine compounds used as peptide coupling reagents.
Synthesis of Tetrazole Ring
Under the action of sodium azide, the cyanide group undergoes [2+3] cycloaddition to generate 5-substituted tetrazoles, which are used in high-energy material research.
Dye and Fragrance Industry
Dye synthesis
Disperse dye
The condensation of m-nitrobenzonitrile with aniline derivatives produces azo dyes containing cyanide groups, which are used for dyeing polyester fibers.
reactive dye
Preparation of dyes containing triazine active groups through sulfonation and diazotization reactions for cotton fabric printing and dyeing.
Spice synthesis
Nitromusk precursor
Participate in the synthesis of macrocyclic musk compounds, endowing the fragrance with a long-lasting woody aroma.
Fruity essence
3-Nitrobenzonitrile derivatives undergo reduction and esterification reactions to produce ester flavors with peach and apricot aromas.
Safety and Handling
● Toxicity Profile
Acute Toxicity: Classified as Harmful (H302, H312, H332) by GHS standards. Oral LD₅₀ in rats exceeds 2000 mg/kg, but dermal and inhalation exposure may cause irritation.
Chronic Effects: No evidence of carcinogenicity (IARC/NTP not listed), but prolonged exposure may affect the liver or kidneys.
● Storage and Transportation
Storage: In cool, dry, well-ventilated areas away from oxidizers and acids.
Transport: Not regulated under Dangerous Goods Regulations (UN number not assigned), but packaged in tight containers to prevent dust inhalation.
● Personal Protective Equipment (PPE)
Gloves: Nitrile or butyl rubber.
Eye Protection: Goggles with side shields.
Respiratory Protection: N95 masks for dust control; supplied-air systems for large-scale handling.
3-Nitrobenzonitrile exemplifies the synergy between chemical structure and industrial application. Its dual functionality as a nitro and cyano compound enables diverse reactions, making it indispensable in pharmaceuticals, agrochemicals, and advanced materials. While challenges remain in safety and environmental impact, ongoing research in green chemistry and nanotechnology promises sustainable innovations. As industries prioritize efficiency and eco-friendliness, 3-nitrobenzonitrile will continue to play a pivotal role in shaping the future of synthetic chemistry.
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