2,6-Dichloropyrazine, white to light gray crystalline solid, bitter almond flavor, volatile in the air. Harmful substances are harmful to the eyes, respiratory tract and skin due to inhalation, skin contact and accidental swallowing. It is used to synthesize sulfaclopyrazine. Stable under normal temperature and pressure, harmful substances. Inhalation, skin contact and accidental swallowing are harmful and have irritating effects on eyes, respiratory tract and skin. Do not inhale dust. In case of contact with eyes, immediately wash with plenty of water and send to a doctor for treatment, wear appropriate protective clothing, gloves and use protective glasses or masks. It is used to synthesize oxyheterocyclic aromatic hydrocarbons containing nitrogen heterocycles, as intermediates of poultry and livestock health drugs, pharmaceuticals and pesticides, and to prepare sulfaclopyrazine sodium, an anti-inflammatory and antibacterial drug for poultry and livestock.
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Chemical Formula |
C4H2Cl2N2 |
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Exact Mass |
148 |
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Molecular Weight |
149 |
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m/z |
148 (100.0%), 150 (63.9%), 152 (10.2%), 149 (4.3%), 151 (2.8%) |
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Elemental Analysis |
C, 32.25; H, 1.35; Cl, 47.59; N, 18.80 |
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The main uses of 2,6-dichloropyrazine are as follows:
PDE4 (phosphodiesterase 4) is an enzyme that plays a critical role in inflammatory response and immune regulation. By inhibiting the activity of PDE4, inflammation and immune cell activation can be reduced, thereby treating a range of inflammatory diseases. This compound can serve as an intermediate for the synthesis of PDE4 inhibitors, providing important raw materials for the development of novel anti-inflammatory drugs.
Malaria is an infectious disease caused by malaria parasites, posing a serious threat to human health. This compound can serve as an intermediate for the synthesis of anti Plasmodium falciparum drugs, providing important support for the development of new anti malarial drugs. These antimalarial drugs can effectively kill malaria parasites, alleviate patients' symptoms, and reduce the mortality rate of malaria.
INOS (inducible nitric oxide synthase) and nNOS (neuronal nitric oxide synthase) are two enzymes that play important roles in the nervous and immune systems. By inhibiting the activity of iNOS and nNOS, the production of nitric oxide can be reduced, thereby treating a range of neurological and immune system diseases.
This substance can serve as an intermediate for the synthesis of iNOS/nNOS inhibitors, providing important raw materials for the development of novel neural and immunomodulatory drugs.
Protein kinases are a class of enzymes that play a critical role in cellular signaling. By inhibiting the activity of protein kinases, cell signaling pathways can be blocked, thereby treating a range of diseases related to cell proliferation, differentiation, apoptosis, and more.
This substance can serve as an intermediate for the synthesis of protein kinase inhibitors, providing important support for the development of new anti-tumor, anti-inflammatory and other drugs.
In addition to the aforementioned applications, it can also serve as an intermediate in the synthesis of other drugs. For example, it can be used to synthesize compounds with specific pharmacological activities that have potential applications in drug development and treatment.
This compound can be used as a biomaterial or organic compound for research related to life sciences. Its unique chemical structure and properties make it an important reagent in biochemical research, helping scientists to gain a deeper understanding of chemical reactions and biological processes within living organisms. This substance has also been used in vitro to prepare pyrazine and pyridine compounds.
These compounds have wide applications in biochemistry and medicinal chemistry, and can be used as inhibitors of atrial fibrillation kinase, which is of great significance for the treatment and research of cardiovascular diseases. Meanwhile, this compound can also be used for the synthesis of nitrogen-containing heterocyclic oxygen bridged calixarenes. These compounds have special structures and properties in biochemical research, which can be used to construct complex biomolecule models and help scientists gain a deeper understanding of the structure and function of biomolecules.
The compound itself also has certain biological activity. By studying its biological activity, scientists can further understand its mechanism of action and potential application value in living organisms. For example, its impact on biological processes such as cell proliferation, differentiation, and apoptosis can be studied, as well as its potential role in disease treatment and prevention.
In biochemical research, the study of signaling pathways is an important direction. It can serve as a tool for studying signaling pathways, and by observing its impact on signaling pathways in organisms, we can further understand the regulatory mechanisms and functions of signaling pathways.
other purposes
This compound can be used as a monomer or intermediate for the synthesis of certain polymer materials. Polymer materials with specific properties, such as high temperature resistance and chemical corrosion resistance, can be prepared through polymerization reactions. At the same time, the structural characteristics of this substance can be used to prepare materials with special functionalities, such as optoelectronic materials, magnetic materials, etc. These materials have broad application prospects in fields such as electronics, optics, and communication.
This substance can also serve as an intermediate in the synthesis of certain dyes. By introducing different functional groups, dyes with different colors and properties can be prepared to meet the needs of industries such as textiles and printing and dyeing.
A preparation method of 2,6-dichloropyrazine, which comprises the following steps: using glycine, glyoxal, etc. as raw materials, through ammoniation and cyclization, to prepare 2-hydroxypyrazine sodium; 2-hydroxypyrazine sodium reacted with dichlorosulfoxide under the catalysis of N, N-diisopropylethylamine to prepare 2-chloropyrazine; Using pyridine as solvent, 2-chloropyrazine was chlorinated by chlorine gas to produce.
The advantage of this method is that the raw material glycine is cheap and easy to obtain, and phosphorus oxychloride is not used as a chlorination reagent, which greatly reduces the generation of organic phosphorus-containing wastewater, and provides an effective way for the efficient and green industrial production of it.
Method II for producing 2,6-dichloropyrazine:
Feed ratio (mass) pyrazine 1,4-dioxide: phosphorus oxychloride=1: (5.5~6.0)
Put pyrazine 1,4-dioxide and phosphorus oxychloride into the glass-lined chlorination kettle, start the mixing, steam heating and tail gas absorption system, slowly raise the temperature to reflux, and keep the reflux stable for 2h, then conduct vacuum distillation to recover some unreacted phosphorus oxychloride and cool it. Add crushed ice into the neutralization kettle, open the freezing brine cooling system of the neutralization kettle, and drop the reaction liquid and ammonia water under stirring to maintain the feed liquid ph ≈ 7, and control the neutralization temperature to be less than 10 ℃. Then centrifugally filter, add the filter cake to the distillation kettle for vacuum distillation, collect the fraction of 120~122 ℃ at 5.33 kpa, and cool it to obtain white crystals with melting point of 57~58 ℃, and yield ≥ 90%.
Adverse reactions
2,6-dichloropyrazine (CAS number: 4774-14-5) is a white to light gray crystalline solid with a melting point of 53-56 ℃, a boiling point of 187.5 ℃ (760 mmHg), and a flash point greater than 110 ℃. Its chemical structure contains two chlorine atoms replacing the 2nd and 6th positions of the pyrazine ring, endowing it with unique reactivity and toxicity characteristics.
Acute toxicity
Oral LD50 (rat):>500 mg/kg (low acute toxicity, but strong local irritation)
Skin irritation: R36/37/38 (irritates eyes, respiratory system, and skin)
Inhalation hazard: H335 (may cause respiratory irritation)
Chronic toxicity
Long term exposure may lead to skin allergies (such as contact dermatitis) or respiratory allergies (such as asthma like symptoms).
Animal experiments have shown that repeated dose exposure may cause liver and kidney dysfunction (data from studies on similar structural compounds).
Environmental toxicity
Low biodegradability, easy to accumulate in the environment, and moderate toxicity to aquatic organisms such as fish and algae (EC50 1-10 mg/L).
Risk management and protective measures
Engineering Control
Sealed operation
Weighing, transferring, and other operations are carried out in a fume hood or local exhaust equipment.
Automation system
Using pipeline transportation or robot operation to reduce manual contact.
Exhaust gas treatment
Install activated carbon adsorption device to ensure that the emission concentration is less than 0.1 mg/m ³.
Personal protection
Respiratory protection
Dust environment: Use N95 mask or half mask (APF ≥ 10).
Steam environment: Choose organic steam filter canister (such as A-type filter cartridge).
Skin protection
Wear nitrile gloves (thickness ≥ 0.3 mm, penetration time>4 hours).
Wear chemical resistant clothing (material: polytetrafluoroethylene/PTFE, resistant to chemical penetration).
Eye protection
Wear sealed goggles (compliant with ANSI Z87.1 standard).
Emergency response
Skin contact
Immediately remove contaminated clothing and rinse with plenty of flowing water for at least 15 minutes.
For severe cases, wet compress with 2% sodium bicarbonate solution and seek medical attention.
Eye contact
Open the eyelids and rinse continuously with physiological saline or clean water for at least 20 minutes.
Disable neutralizing agents (such as acidic solutions) to avoid secondary damage.
Inhalation exposure
Quickly transfer to a well ventilated area and keep the respiratory tract unobstructed.
Oxygen therapy (flow rate 5 L/min), tracheal intubation if necessary.
Leakage disposal
Minor leakage: Absorb with sand or vermiculite and collect in a sealed container.
Massive leakage: Construct a dam and transfer it to a tanker or dedicated collector using an explosion-proof pump.
Frequently Asked Questions
Why does its melting point fluctuate? 54 ° C or 58 ° C?
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Because there are purity illusions and measurement differences. The melting point range reported by different suppliers is between 52-58 ° C, with Sigma indicating 55-58 ° C and TCI indicating 53-56 ° C. This difference is due to slight variations in product purity (98% -99%) and crystal morphology - the melting point of 2,6-dichloropyridine is highly sensitive to impurities and serves as a "barometer" for quickly assessing batch quality.
Is it a twin of 2,3-dichloropyrazine? What are the differences in reactivity?
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No, the relative position of chlorine atoms determines fate. The two chlorine atoms of 2,6-dichloropyrazine are in the para position and are synergistically activated by the two nitrogen atoms in the pyrazine ring, resulting in extremely high nucleophilic substitution reactivity; The chlorine atom of 2,3-dichloropyrazine is located in the adjacent position, resulting in spatial hindrance and differences in electronic effects. Research has shown that in amination reactions containing amantadine, the 2,6-isomer exhibits the best yield.
Why is there two versions of its storage temperature: "room temperature" and "refrigerated"?
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This is a game between "short-term convenience" and "long-term stability". TCI and other suppliers indicate that the room temperature (<15 ° C) should be cool and avoid light; And Chem Impex explicitly requires refrigeration at 0-8 ° C. Compromise suggestion: Store in a refrigerator at 2-8 ° C for long-term use, and seal in a dry and cool place for short-term use. The key is to avoid light and moisture, as it is sensitive to moisture.
Are its two chlorine atoms "equivalent"? Can we replace them one by one?
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It is chemically equivalent, but the reaction can be controlled step by step. Due to molecular symmetry, two chlorine atoms are completely identical in their electronic environment. But in nucleophilic substitution reactions, by controlling the reaction conditions (temperature, feed ratio, nucleophilic reagent equivalent), high selectivity can be achieved for single substitution, generating 2-chloro-6-substituted pyrazine intermediates, and then performing the second step of substitution. This is a key strategy for constructing 2,6-symmetric substitution products.
Apart from being used as a pesticide, what other niche materials can it "cross over" to make?
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Yes! It is the building block of oxacalixarenes. By utilizing its two chlorine atoms as reaction sites and nucleophilic substitution with bisphenol compounds, a macrocyclic supramolecular host containing pyrazine rings can be constructed. This type of material has unique applications in molecular recognition and host guest chemistry, as the pyrazine ring provides additional nitrogen coordination sites.
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