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2-Chloronicotinic acid is an organic compound with CAS 2942-59-8 and chemical formula C6H4ClNO2. It is a white crystalline powder. The solubility in water is relatively low, about 0.9 grams per 100 milliliters of water. When burned in the air, toxic nitrogen oxide gases are produced. It has good solubility in common organic solvents such as ethanol, acetone, and dimethyl sulfoxide. It is an organic acid with an acidic aqueous solution and a pH value below 7. It is an asymmetric molecule and therefore has chirality. It can have two chiral isomers, namely left-handed and right-handed.
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Chemical Formula |
C6H4ClNO2 |
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Exact Mass |
157 |
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Molecular Weight |
158 |
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m/z |
157 (100.0%), 159 (32.0%), 158 (6.5%), 160 (2.1%) |
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Elemental Analysis |
C, 45.74; H, 2.56; Cl, 22.50; N, 8.89; O, 20.31 |
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Melting point 42-45 ? C , Boiling point 109.7 ° C , Density 1.25 ( 14 % aq. ) , Refractive index n20 / D 1.378 , Storage Conditions Refrigerator , Acidity coefficient ( pKa ) -4.06 ± 0.40 ( Predicted ) , stable. Incompatible with strong oxidizing agents. , Hazardous mark C, N, T, Xn , Hazard category code 34-43-50-20 / 21 / 22-50 / 53-23 / 24 / 25-42 / 43 , Safety instructions 26-36 / 37 / 39-45-60-61-24-28-36 / 37-23 , Transport of dangerous goods No.UN 1760 8 / PG 2 , WGK Germany 1 , RTECS NX8156850 , HazardClass 8 ,Packing Group III.
2-chloronicotinic acid (chemical name: 2-chloro-3-pyridinecarboxylic acid) is an important fine chemical intermediate, which has a wide range of applications in various fields such as pesticides, pharmaceuticals, dyes, etc. due to its unique chemical structure and physiological activity.
1. Herbicide synthesis
Fipronil: a key intermediate for the synthesis of sulfonylurea herbicide Fipronil. Nicotine sulfometuron is an efficient, low toxicity, and broad-spectrum herbicide widely used in crop fields such as corn and wheat, which can effectively control various annual and perennial weeds.
Pifluoroacetamide: It is also an important intermediate of the amide herbicide Pifluoroacetamide. Pifluoroacetamide has intrinsic absorption conductivity and can be absorbed by the roots and leaves of weeds, interfering with their photosynthesis and achieving weed control effects.
Other herbicides: They can also be used to synthesize other types of herbicides, such as fluazinam, which play an important role in agricultural production.
Synthesis of fungicides
Imidacloprid: can be used to synthesize amide fungicides such as Imidacloprid. Imidacloprid is a broad-spectrum, systemic fungicide that has good control effects on various crop diseases such as gray mold and rot.
Other fungicides: Its derivatives can also be used to synthesize other types of fungicides, providing comprehensive disease protection for crops.
Advantages of pesticide intermediates
Efficiency: Synthetic pesticide products usually have the characteristics of high efficiency, low toxicity, and broad spectrum, which can meet the requirements of modern agriculture for pesticide performance.
Environmental friendliness: With the increasing awareness of environmental protection, the requirements for the environmental friendliness of pesticides are also becoming higher and higher. Synthetic pesticide products typically have minimal environmental impact and meet the requirements of sustainable development.
Market demand growth: With the development of global agriculture, the demand for efficient and environmentally friendly pesticides continues to increase. As a pesticide intermediate, its market demand is also showing a growing trend.
Medical field
1. Anti AIDS drugs
Nevirapine is a key intermediate for the synthesis of HIV reverse transcriptase inhibitor Nevirapine. Nevirapine can delay the progress of AIDS by inhibiting the reverse transcriptase activity of HIV virus and preventing virus replication.
Other anti AIDS drugs: its derivatives can also be used to synthesize other types of anti AIDS drugs, providing more treatment options for AIDS patients.
2. Antidepressant drugs
Mirtazapine: can be used to synthesize the antidepressant drug Mirtazapine. Mirtazapine improves depression symptoms and enhances patients' quality of life by regulating neurotransmitter levels.
Other antidepressants: Its derivatives can also be used to synthesize other types of antidepressants to meet the treatment needs of different patients.
3. Anti-inflammatory and analgesic drugs
Niflufenamic acid: an important intermediate for the synthesis of nonsteroidal anti-inflammatory and analgesic drug Nifluamic acid. Niflufenamic acid exerts anti-inflammatory and analgesic effects by inhibiting prostaglandin synthesis, and is widely used in the treatment of painful diseases such as rheumatoid arthritis and osteoarthritis.
Pralofen: It can also be used to synthesize the anti-inflammatory drug Pralofen. Pralofen has anti-inflammatory, antipyretic, and analgesic effects, and is commonly used to treat inflammation in ophthalmology, otolaryngology, and other fields.
Other anti-inflammatory and analgesic drugs: Their biology can also be used to synthesize other types of anti-inflammatory and analgesic drugs, providing effective treatment methods for pain patients.
4. Other pharmaceutical products
Animal anti-inflammatory drugs, such as flunixin meglumine, can also be used to synthesize animal anti-inflammatory drugs, providing important drug support for animal husbandry.
Advantages of pharmaceutical intermediates:
Diversity: There are a wide range of synthetic medical products, covering many fields such as anti AIDS, antidepressant, anti-inflammatory and analgesic, meeting the treatment needs of different diseases.
Innovation: With the continuous development of pharmaceutical technology, the demand for new drugs is constantly increasing. As a pharmaceutical intermediate, it provides an important material basis for the development of new drugs.
Market potential: With the growth of the global population and the intensification of aging trends, the demand for pharmaceutical products continues to increase. As a pharmaceutical intermediate, its market potential is enormous.
Dye field
Dye intermediates: can also be used as dye intermediates for synthesizing specific types of dyes. These dyes have a wide range of applications in the textile, printing and dyeing industries, providing rich color choices for products.
Advantages of dye intermediates:
Color richness: Synthetic dye products have bright and diverse colors, which can meet the color needs of different industries.
Stability: These dyes usually have good stability and can maintain vivid colors in different environments, extending the product's service life.
Metal ligands: their derivatives such as 2,2 '- diselenino nicotinic acid can be used as metal ligands and have important applications in the fields of metal organic chemistry and coordination chemistry.
Research and teaching: 2-chloronicotinic acid, as an important chemical intermediate, can also be used in research and teaching fields, providing an important material basis for chemical research.
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It can be synthesized from 3-cyanopyridine (2) through oxidation, chlorination, and hydrolysis reactions.
C6H4N2 (2)+H2O2+NaOH+CuCl2+5HCl → C6H4ClNO2+CuCl+2H2O+NH4Cl+Na
Firstly, react 3-cyanopyridine (2) with sodium hydroxide (NaOH) and hydrogen peroxide (H2O2) in an appropriate solvent for oxidation reaction. In this step, sodium hydroxide acts as a catalyst and provides alkaline conditions.
C6H4N2 (2)+H2O2+NaOH → 3-Cyanopyridine (2)-N-oxide+H2O+Na
Next, the oxidation product is reacted with cuprous chloride (CuCl2) and hydrochloric acid (HCl) in an appropriate solvent for chlorination reaction. In this step, cuprous chloride acts as a catalyst, promoting the chlorination reaction.
C6H4N2 (2)-N oxide+CuCl2+4HCl → 3-cyanopyridine (2)-N chloride+CuCl+2H2O
Finally, the chlorinated product is hydrolyzed with water (H2O) under appropriate conditions to produce the final product. In this step, acidic conditions promote the hydrolysis reaction.
C6H4N2 (2)-N chloride+H2O → C6H4ClNO2+NH4Cl
A mixture of 2-Chloronicotinic acid and 2-chloro-5-methylpyridine can be prepared by the following steps:
1. React 3-methylpyridine with hydrogen peroxide to produce n-oxo-3-methylpyridine. This reaction is an oxidation reaction, in which hydrogen peroxide serves as an oxidant to oxidize 3-methylpyridine to n-oxo-3-methylpyridine. This step can use different reaction conditions and oxidants to achieve the best yield and purity.
C6H7N+H2O2 → C6H7NO
2. Cyclically chlorinate n-oxo-3-methylpyridine with phosphorus oxychloride to obtain a mixture of 2-chloro-5-methylpyridine and 2-chloro-3-methylpyridine. This reaction is a chlorination reaction, in which phosphorus oxychloride serves as a chlorinating agent, replacing the hydroxyl group in n-oxo-3-methylpyridine with a chlorine atom to produce a mixture of 2-chloro-5-methylpyridine and 2-chloro-3-methylpyridine. This step requires controlling the reaction conditions, such as temperature, reaction time, and concentration, to achieve the best yield and purity.
C6H7NO+PCl3 → C6H6ClN+C6H6ClN
3. In the presence of acid binding agent diisopropylamine, a mixture of 2-chloro-5-methylpyridine and 2-chloro-3-methylpyridine is used as a chlorinating agent for crystallization and distillation. The purpose of this step is to separate 2-chloro-5-methylpyridine and 2-chloro-3-methylpyridine through crystallization and distillation. The conditions for crystallization and distillation can be adjusted according to specific circumstances to improve yield and purity.
4. Convert 2-chloro-3-methylpyridine to 2-chloro-3-trichloromethylpyridine through side chain chlorination. This reaction is a side chain chlorination reaction, in which chlorine gas acts as a chlorinating agent, replacing the side chain of 2-chloro-3-methylpyridine with a chlorine atom to generate 2-chloro-3-trichloromethylpyridine. This step requires controlling reaction conditions such as temperature, pressure, and concentration to achieve the best yield and purity.
C6H6ClN+Cl2 → C6H5Cl3N
5. Hydrolyze 2-chloro-3-trichloromethylpyridine to obtain 2-chloro-3-pyridinecarbonyl chloride or 2-chloro-3-pyridinecarboxylic acid. This reaction is a hydrolysis reaction, in which water serves as the reaction reagent, replacing three chlorine atoms in 2-chloro-3-trichloromethylpyridine with hydroxyl groups to produce 2-chloro-3-pyridinecarbonyl chloride or 2-chloro-3-pyridinecarboxylic acid. This step requires controlling reaction conditions such as temperature, pH, and concentration to achieve the best yield and purity.
C6H5Cl3N+H2O → C6H4ClNOCl/C6H4ClNO2
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