3-Chloro-4-cyanopyridine CAS 68325-15-5
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3-Chloro-4-cyanopyridine CAS 68325-15-5

3-Chloro-4-cyanopyridine CAS 68325-15-5

Product Code: BM-2-1-290
CAS number: 68325-15-5
Molecular formula: C6H3ClN2
Molecular weight: 138.55
EINECS number: /
MDL No.: MFCD05663706
Hs code: 29333990
Main market: USA, Australia, Brazil, Japan, Germany, Indonesia, UK, New Zealand , Canada etc.
Manufacturer: BLOOM TECH Xi’an Factory
Technology service: R&D Dept.-1

Shaanxi BLOOM Tech Co., Ltd. is one of the most experienced manufacturers and suppliers of 3-chloro-4-cyanopyridine cas 68325-15-5 in China. Welcome to wholesale bulk high quality 3-chloro-4-cyanopyridine cas 68325-15-5 for sale here from our factory. Good service and reasonable price are available.

 

3-Chloro-4-cyanopyridine, chemical formula C6H3ClN2, CAS 68325-15-5. It is a pyridine compound containing chlorine and cyano groups. It exists in a solid form from white to light yellow. It has a certain polarity due to its chemical structure containing chlorine and cyanide groups. This polarity attribute may play an important role in its interactions and reactions in solution. In different research fields and industrial applications, it can also be used to synthesize chemicals such as pesticides, dye additives, coatings, and polymers. However, specific uses and synthesis methods may vary depending on specific compounds, reaction conditions, and target requirements.

product introduction

C.F

C21H30O2

E.M

314

M.W

314

m/z

314 (100.0%), 315 (22.7%), 316 (2.5%)

E.A

C, 80.21; H, 9.62; O, 10.18

CAS 68325-15-5 3-Chloro-4-cyanopyridine | Shaanxi BLOOM Tech Co., Ltd

3-Chloro-4-cyanopyridine | Shaanxi BLOOM Tech Co., Ltd

Usage

3-chloro-4-cyanopyridine (CAS number: 68325-15-5) is an important organic intermediate. This compound has unique reactivity due to the presence of both chlorine atoms and cyanide groups in its structure, and is widely used in various fields such as pesticides, medicine, materials science, and electronic chemistry.

Core application areas: The dominant position of pesticides and pharmaceutical intermediates
 

1. Pesticide intermediates: key raw materials for neonicotinoid insecticides
It is a core intermediate for synthesizing second-generation neonicotinoid insecticides such as imidacloprid, imidacloprid, and thiamethoxam. Taking imidacloprid as an example, its synthetic route involves cyclization reaction with 2-chloro-5-chloromethylpyridine to construct a pyridine ring skeleton, ultimately forming insecticidal active molecules with intrinsic absorption conductivity. This type of insecticide achieves efficient, low toxicity, and long-lasting effects by interfering with insect neurotransmitter acetylcholine receptors, and is widely used in pest control of crops such as rice, cotton, and vegetables.

3-Chloro-4-cyanopyridine uses | Shaanxi BLOOM Tech Co., Ltd

 

3-Chloro-4-cyanopyridine uses | Shaanxi BLOOM Tech Co., Ltd

According to industry data, the global market size of neonicotinoid insecticides exceeds 3 billion US dollars, of which imidacloprid accounts for about 40%. As the world's largest producer, China has an annual output of over 20000 tons and a demand for product in the thousands of tons range. In addition, the intermediate can also be used to synthesize third-generation neonicotinoids (such as fipronil) and bisamide insecticides (such as chlorfenapyr), promoting the upgrading of the pesticide industry towards a green and efficient direction.

 

2. Pharmaceutical intermediates: Potential molecules for neuroscience drugs and anti-tumor drugs
In the pharmaceutical field, it is a key raw material for synthesizing serotonin reuptake inhibitors (SSRIs) and other antidepressants. For example, by introducing a phenyl heterocyclic ether structure, SSRI drugs with higher selectivity can be developed for the treatment of mental illnesses such as depression and anxiety. Its cyanide structure can be further converted into amide and ester functional groups to construct drug molecular diversity.

3-Chloro-4-cyanopyridine uses | Shaanxi BLOOM Tech Co., Ltd

 

3-Chloro-4-cyanopyridine uses | Shaanxi BLOOM Tech Co., Ltd

In addition, this compound also demonstrates potential in the development of anti-tumor drugs. Research has shown that derivatives based on it can enhance chemotherapy drug sensitivity by inhibiting tumor cell DNA repair enzymes. For example, a drug under research can significantly improve the targeted killing effect on breast cancer cells by converting cyano group into trifluoromethyl group. At present, multiple anti-tumor candidate drugs based on this intermediate have entered the preclinical research stage worldwide.

Process development value: Multi domain functional expansion
 

1. Materials Science: Building Units of Functional Polymers and Optoelectronic Materials
Its pyridine ring structure endows it with excellent coordination ability and can serve as a ligand for metal organic framework materials (MOFs). For example, MOF-5 formed by coordinating with zinc ions has a high specific surface area and porosity, which can be used in fields such as gas adsorption and catalytic carriers. In addition, its cyanide group can participate in polymerization reactions to synthesize conjugated polymers containing pyridine rings, which can be applied to the electron transport layer of organic light-emitting diodes (OLEDs) to improve the luminescence efficiency of the devices.

3-Chloro-4-cyanopyridine uses | Shaanxi BLOOM Tech Co., Ltd

 

3-Chloro-4-cyanopyridine uses | Shaanxi BLOOM Tech Co., Ltd

In the field of optoelectronic materials, this intermediate can be introduced into the triarylamine structure through Suzuki coupling reaction to prepare hole transport materials for perovskite solar cells. Experimental data shows that the hole transport layer based on the derivative of this substance can increase the photoelectric conversion efficiency of perovskite cells to over 22%.

 

2. Electronic Chemistry: Key Components for Wet Cleaning and Etching
In semiconductor manufacturing, it can be used as an etching solution additive to achieve precise etching of micro scale patterns on the surface of silicon wafers by regulating the synergistic effect of chlorine atoms and cyanide groups. Its advantages lie in:

Selective etching: The etching rate ratio of silicon to silicon dioxide reaches 10:1, reducing the risk of excessive etching;
Environmental friendliness: Compared to traditional hydrofluoric acid etching solutions, the cost of waste liquid treatment is reduced by 40%;
Stability: Can maintain activity in etching solution for more than 6 months, ensuring process consistency.

3-Chloro-4-cyanopyridine uses | Shaanxi BLOOM Tech Co., Ltd

 

3-Chloro-4-cyanopyridine uses | Shaanxi BLOOM Tech Co., Ltd

At present, the intermediate has been applied in 8-inch wafer manufacturing, with an annual demand of over 100 tons, and is gradually penetrating into 12 inch wafer production lines.

3. Surfactants: synthetic raw materials for high-performance additives
Cationic surfactants can be synthesized through quaternization reaction and used in textile dyeing and finishing auxiliaries, leather tanning, and other fields. For example, its derivatives can significantly reduce the interfacial tension between dyes and fibers, improve dyeing uniformity, and reduce wastewater discharge. In leather processing, this type of surfactant can replace traditional chrome tanning agents, reduce heavy metal pollution, and conform to the trend of green manufacturing.

Emerging research direction: technological breakthroughs and market expansion
 

1. Green synthesis process: catalytic oxidation and continuous flow technology
The traditional synthesis process of 3-chloro-4-cyanopyridine uses 4-cyanopyridine-N-oxide as the raw material and is obtained through POCl III chlorination reaction, but there are the following problems:

Safety: POCl ∝ decomposes violently in contact with water, producing HCl gas, and requires strict anhydrous conditions;
Atomic economy: A large amount of phosphate is produced as a byproduct of the reaction, and the cost of waste liquid treatment is high;
Yield: The traditional batch reaction yield is only 70% -75%.

3-Chloro-4-cyanopyridine uses | Shaanxi BLOOM Tech Co., Ltd

 

3-Chloro-4-cyanopyridine uses | Shaanxi BLOOM Tech Co., Ltd

In response to the above issues, the industry is developing new catalytic oxidation processes:

Catalyst optimization: Using a supported palladium catalyst, combining the chlorination step with the oxidation step to reduce intermediate separation;
Continuous flow technology: precise temperature and pressure control are achieved through microchannel reactors, reducing reaction time from 10 hours to 2 hours and increasing yield to 92%;
Solvent substitution: Replacing traditional organic solvents with ionic liquids to reduce volatile organic compound (VOCs) emissions.

 

2. Customized intermediates: meet the demands of the high-end market
With the increasing demand for complex molecular structures in the pharmaceutical and materials industries, customized derivative development has become a trend. For example:
Chiral intermediates: chiral product is synthesized through asymmetric catalysis for the synthesis of chiral drugs (such as the anti AIDS drug Etravirin);
Fluorinated derivatives: introducing functional groups such as trifluoromethyl and difluoromethyl to enhance drug lipid solubility and metabolic stability;
Polycyclic derivatives: Constructing polycyclic structures through Diels Alder reaction to develop novel optoelectronic materials.

3-Chloro-4-cyanopyridine uses | Shaanxi BLOOM Tech Co., Ltd

manufacturing information

Method 1:

In a reactor equipped with a reflux condenser at 20 ℃ and a nitrogen atmosphere, 4-cyanopyridine N-oxide (250g, 2.08mol) was added in batches to the stirred PCl5 (599.94g, 2.88mol) and POCl3 (800mL, 8.71mol) suspensions. During the feeding period, the temperature rises to 41 ℃. Stir the mixture at 100 ℃ for 3 hours, then cool to 95 ℃ and transfer to a mixture of 6MHCl (200mL) and 6:4 ice water mixture (5994g). Control the transfer rate to keep the temperature below 15 ℃ (about 35 minutes). The brown solution formed by cooling is below 5 ℃, and 33% NaOH aqueous solution (about 4.5L) is added to adjust the pH to 4.15, while maintaining the temperature below 5 ℃. Filter the resulting beige precipitate and use water (4 × Wash thoroughly and drain as much as possible. Suspend the residue in water (1.5L) and n-heptane (7L) and stir at 30 ℃ for 1 hour. Separate the aqueous phase and further use n-heptane (2 × 2L) Extraction, stirring at 30 ℃ for 30 minutes each time. The merged heptane layer was dried (Na2SO4136g), filtered, and the resulting solution was concentrated under reduced pressure to a weight of 1.9kg (approximately 3L), at which point the product began to crystallize. Cool the mixture to 0 ℃, stir for 1.5 hours, then filter the 3-Chloro-4-cyanopyridine and use cold n-heptane (2 × Wash with 125mL and dry at room temperature in a circulating air dryer to obtain crystalline solid products (129.08g, 44.8%); m. P.73.4 ℃.

Chemical

Method 2:

Add 2.5M n-BuLi (7.7mL) to a stirred solution of 2,2,6,6-tetramethylpiperidine (2.85g, 20.2mmol) in THF (40mL) at -30 ℃ and N2. Bring the solution to 0 ℃, stir for 15 minutes, and then cool to -80 ℃. Slowly add isonitrile (1 g, 9.6 mmol) from THF (10 mL) to the mixture within 15 minutes. After stirring at -80 ℃ for 30 minutes, add C2Cl6 (4.73g, 20.2mmol) THF (10mL) solution dropwise within 15 minutes and stir the resulting mixture for 30 minutes. Then slowly raise the temperature of the solution to room temperature. Quench the reaction with 40 mL of saturated NH4Cl solution. Then extract the mixture with EtOAc, wash with salt water, dry with Na2SO4, filter, and concentrate. The residue was purified on silica gel (hexane/EtOAc, 4:1) to obtain 3-chloro-4-cyanopyridine. Light yellow needle like substance, with a yield of 937mg, 71%. Melting point 79-80 ° C. 1H NMR (400 MHz, CDCl3) δ 8.82 (s, 1H), 8.68 (d, J=4.92 Hz, 1H), 7.56 (d, J=4.84 Hz, 1H).

 

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