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3-Nitrobenzaldehyde 99% is an organic compound with the molecular formula C7H5NO3, CAS 99-61-6, and a molecular weight of 151.13. Usually yellow or brown crystalline or solid powder. Its color may vary depending on purity, batch, or storage conditions. It is soluble in water, but soluble in hot water. In organic solvents such as ether and chloroform, it also has good solubility. It is a weakly acidic compound with a pKa value of around 7. This means that it can exist stably under acidic and alkaline conditions, but tends to exhibit better stability under acidic conditions. It is a multifunctional organic intermediate that can react with many other compounds to synthesize other organic compounds. For example, it can react with alcohols to form ester compounds; React with aldehydes to form ketone compounds; React with amines to generate amide compounds, etc. These compounds have extensive application value in fields such as chemical engineering, medicine, and pesticides.
|
C.F |
C7H5NO3 |
|
E.M |
151 |
|
M.W |
151 |
|
m/z |
(100.0%), 152 (7.6%) |
|
E.A |
C, 55.64; H, 3.34; N, 9.27; O, 31.76 |
|
M.P |
56 ° C |
|
B.P |
285-290 ° C |
|
Density |
1.2792 |
|
V.D |
5.21 (vs air) |
|
R.I |
1.5800 (estimated) |
|
|
|
3-Nitrobenzaldehyde 99% (chemical formula: C ₇ H ₅ NO ∝, CAS number: 99-61-6) is an aromatic aldehyde compound with dual functional groups of nitro (- NO ₂) and aldehyde (- CHO). Its physical properties are manifested as light yellow or off white crystals, with a melting point of 58-59 ℃, a boiling point of 164 ℃ (3.06kPa), a relative density of 1.2792 (20/4 ℃), soluble in organic solvents such as alcohols, ethers, chloroform, benzene, and acetone, almost insoluble in water, and capable of steam distillation. As an important organic synthesis intermediate, m-nitrobenzaldehyde has a wide range of applications in pharmaceuticals, dyes, surfactants, and life sciences, and its market demand continues to expand with the upgrading of downstream industries.
It is a key raw material for synthesizing dihydropyridine calcium channel blockers, which reduce vascular smooth muscle tone by inhibiting calcium ion influx and are widely used in the treatment of cardiovascular diseases such as hypertension and angina. In the synthesis of drugs represented by nitrendipine, nifedipine, and nicardipine, the core structure of the dihydropyridine ring is constructed through the condensation response of aldehyde and amino groups, and the nitro group serves as the positioning group for subsequent reduction responses. For example, in the synthesis route of nitrendipine, the substance is condensed with methyl acetoacetate and ammonia under alkaline conditions, and the target product is obtained through steps such as nitro reduction and salt formation, with a total yield of over 75%.
In addition to calcium channel blockers, it is also involved in the synthesis of contrast agents such as calcium iodopusphate and iodopuric acid, as well as vasoactive drugs such as meta hydroxylamine bitartrate. In the production of calcium iodide, its aldehyde group reacts with hydroxylamine to form oxime, which is then iodized and salted to obtain the final product. This contrast agent is widely used in vascular imaging due to its high hydrophilicity. According to statistics, the global market size of calcium channel blockers has exceeded 20 billion US dollars, with China accounting for over 30%, indirectly driving the annual demand for m-nitrobenzaldehyde to thousands of tons.
Its nitro and aldehyde groups can participate in various dye synthesis responses. In the field of dispersed dyes, the Schiff base generated by its condensation with aromatic amines can be oxidized and closed to form anthraquinone dyes. For example, in the synthesis of Disperse Blue 2BLN, the target dye is obtained by condensation with p-nitroaniline and oxidation with chromic acid, which accounts for more than 15% of the dispersed dye market share. In terms of acidic dyes, aromatic amines substituted with aldehyde and sulfonic acid groups can react to generate azo dyes, which are used for dyeing protein fibers such as wool and silk.
In addition, meta aminobenzaldehyde can be prepared through reduction response, which is an important intermediate for the synthesis of cationic dyes and reactive dyes. For example, the reactive yellow X-R generated by the response of meta aminobenzaldehyde with cyanuric chloride is widely used for cotton fiber dyeing due to its high reactivity. With the tightening of environmental regulations, the demand for low toxicity and high fastness dyes has increased, with an average annual growth rate of 8% in the use of functional dyes.
The aldehyde group of m-nitrobenzaldehyde can undergo condensation response with long-chain alkyl primary amines to form Schiff base surfactants. This type of surfactant has excellent emulsifying and dispersing properties due to its strong polar nitro groups, and is widely used in fields such as petroleum extraction, textile printing and dyeing. For example, in tertiary oil recovery, it can be used as a displacement agent to reduce the interfacial tension between oil and water to below 10 ⁻ mN/m, and increase the recovery rate by 5% -10%.
In addition, 3-Nitrobenzaldehyde 99% can also participate in the synthesis of fluorinated surfactants. Fluorine containing Schiff base surfactants can be prepared by condensation with perfluoroalkyl primary amine and hydrogenation reduction of nitro group. These products are used in electronic grade cleaning agents, fire foam and other fields due to their low surface tension characteristics. According to market research institutions' predictions, the global market size of specialty surfactants will exceed 20 billion US dollars by 2025, with nitroaromatic aldehyde surfactants accounting for 12%.
Life Sciences: Biochemical Reagents and Drug Analysis
It has dual application value in the field of life sciences. As a biochemical reagent, its aldehyde group can undergo Schiff base response with lysine residues in proteins, and is used in biotechnology such as protein immobilization and immunoassay. For example, in enzyme-linked immunosorbent assay (ELISA), the modified carrier protein can enhance antigen antibody binding specificity and reduce background interference.
In the field of pharmaceutical analysis, it is a specialized reagent for trace detection of phenolic compounds. It undergoes condensation response with phenols under alkaline conditions, producing colored products. The content of phenolic impurities in drugs can be quantitatively detected by spectrophotometry. This method has a sensitivity of 0.1 μ g/mL and is included as the standard method for impurity detection of drugs such as aspirin and acetaminophen in the Chinese Pharmacopoeia.
With the deepening of interdisciplinary research, its applications in emerging fields are gradually expanding. In the field of materals science, it participates in the synthesis of conjugated polymers as a monomer, and introduces amino groups through nitro reduction to prepare amino containing conjugated polymers. This material is used in fields such as fluorescence sensors and organic light-emitting diodes (OLEDs) due to its high fluorescence quantum yield.
In the field of environmental engineering, the nitro group of m-nitrobenzaldehyde can be reduced to an amino group, generating m-aminobenzaldehyde. The latter, as a chelating agent for heavy metal ions, can efficiently adsorb heavy metal ions such as Pb ² ⁺ and Cd ² ⁺ in wastewater, with an adsorption capacity of over 150mg/g. In addition, its aldehyde group can react with formaldehyde to form phenolic resin modifiers, which improve the heat resistance and mechanical strength of the resin and meet the needs of high-end composite materals.
3-Nitrobenzaldehyde 99% can be obtained by nitrating benzaldehyde with nitric acid. This is a commonly used synthesis method, with readily available raw materals and relatively mild response conditions.
The chemistry equation for the synthesis of 3-Nitrobenzaldehide through nitration reaction is as follows:
CH3CHO + HNO3 → CH3CHO3 + H2O
In this chemistry equation, CH3CHO represents the oxidation of aldehyde groups in benzaldehyde molecules to carboxylic acid groups; HNO3 represents the combination of hydrogen ions and oxygen ions in nitric acid molecules to form water molecules; CH3CHO3 indicates that the aldehyde groups in the generated 3-Nitrobenzaldehide molecules are oxidized to carboxylic acid groups and nitrated to nitro groups; H2O represents the generated water molecules.
Experimental principle:
Nitrification response is a common organic synthesis method commonly used to prepare organic compounds containing nitro groups. In this experiment, we will use benzaldehyde and nitric acid as raw materals to synthesize 3-Nitrobenzaldehide through nitration response.
Experimental steps:
1. Preparation of raw materals: Prepare an appropriate amount of benzaldehyde and nitric acid according to the experimental requirements. Ensure that the purity of benzaldehyde and nitric acid meets the experimental requirements.
2. Mixed raw materals: Mix benzaldehyde and nitric acid in a certain proportion together. Usually, the amount of nitric acid used is slightly higher than that of benzaldehyde to ensure the progress of the response. During the mixing process, it is necessary to pay attention to stirring evenly to ensure full contact between the two raw materals.
3. Nitrification response: The mixture is subjected to nitrification response under heating conditions. During the response, nitric acid undergoes a nitration response with the aldehyde group in benzaldehyde, producing 3-Nitrobenzaldehide. Nitrification response is an exothermic response, and temperature control is very important. Excessive temperature may lead to side responses, affecting the purity and yield of the product. Therefore, during the experimental process, it is necessary to strictly control the temperature and response time.
4. Separation and purification: After the response is completed, the generated 3-Nitrobenzaldehide is separated by distillation, extraction, and other methods. Then, purification was carried out through steps such as recrystallization and drying to obtain high-purity 3-Nitrobenzaldehide. During the separation and purification process, attention should be paid to operational details to avoid introducing impurities and by-products.
Product detection: Structural characterization and purity detection of the generated 3-Nitrobenzaldehide were performed using infrared spectroscopy, nuclear magnetic resonance, and other methods.
Precautions
1. Purity control of raw materals: The purity of benzaldehyde and nitric acid has a significant impact on the response results. Therefore, strict purity checks and quality control of the raw materals are required before the experiment. If the raw material contains impurities or by-products, it may affect the purity and yield of the product.
2. Temperature control: Nitrification response is an exothermic response, and temperature control is very important. Excessive temperature may lead to side responses, affecting the purity and yield of the product. Therefore, strict control of temperature and response time is required during the experimental process.
3. Operational details: During the separation and purification process, attention should be paid to operational details to avoid introducing impurities and by-products. For example, during the distillation process, it is necessary to pay attention to controlling temperature and pressure to avoid phenomena such as boiling or funnel; During the extraction process, attention should be paid to selecting appropriate extractants and extraction conditions to ensure extraction efficiency and product purity.
4. Product preservation: The generated 3-Nitrobenzaldehide needs to be properly preserved to avoid spoilage or oxidation caused by contact with air.
3-Nitrobenzaldehyde 99% is an important organic compound with various unique chemistry properties.
1. Reaction of aldehyde groups
Due to the presence of aldehyde groups (-CHO) in the 3-Nitrobenzaldehide molecule, it can undergo a series of responses related to aldehyde groups. For example, it can react with primary or secondary amines to generate corresponding imines (Schiff bases). This response has important applications in biochemistry and organic synthesis.
R-CHO+R '- NH2 → R-CH=NR'+H2O
2. Reaction of nitro groups
The nitro group (-NO2) in the 3-Nitrobenzaldehide molecule gives it some unique chemistry properties. Nitro groups can be reduced to amino groups (-NH2), which is one of the common responses in nitro compounds. In addition, nitro groups can also participate in nucleophilic substitution reactions, such as reacting with halogens or alcohols to generate corresponding nitro derivatives.
Ar-NO2 + 2[H] → Ar-NH2 + H2O
Ar-NO2 + X2 → Ar-X+ 2NO2 (X=Cl, Br, I)
Ar-NO2 + ROH → Ar-OR + HNO3
3. Reaction of benzene ring
The benzene ring in the 3-Nitrobenzaldehide molecule can undergo a series of aromatic electrophilic substitution responses, such as nitration, sulfonation, halogenation, etc. These responses typically have important applications in the synthesis and modification of aromatic compounds.
Ar-H+NO2+H+→ Ar-NO2+H2O (nitrification)
Ar-H+SO3 → Ar-SO3H (sulfonation)
Ar-H+X2 → Ar-X+HX (halogenated, X=Cl, Br, I)
4. Oxidation reaction
3-Nitrobenzaldehide can be oxidized to the corresponding carboxylic acid. This response is commonly used in organic synthesis to construct carboxylic acid functional groups.
ArCHO + [O] → ArCOOH
5. Reduction reaction
3-Nitrobenzaldehide can be converted into corresponding alcohols or amines through reduction responses. These reduction responses have a wide range of applications in organic synthesis, such as for constructing alcohol or amine functional groups.
Ar CHO+[H] → Ar CH2OH (reduced to alcohol)
Ar-CHO+ NH3 + [H] → Ar-CH2NH2 + H2O (reduced to amine)
6. Reaction with Grignard reagent
3-Nitrobenzaldehide can react with Grignard reagent to generate corresponding ketones. This response is commonly used in organic synthesis to construct carbon carbon bonds.
Ar CHO + RMgX → Ar COR+ MgX2 (X=Cl, Br, I)
7. Reactions with other carbonyl compounds
3-Nitrobenzaldehide can undergo condensation responses with other carbonyl compounds (such as ketones, esters, etc.) to form α,β- Unsaturated carbonyl compounds. These responses are commonly used in organic synthesis to construct carbon carbon double bonds.
Ar CHO + R'COR "→ Ar CH=CHCOR" + R'OH (condensation reaction)
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