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The chemical compound 3,5-dibromo-2(1H)-pyridinone is an important intermediate in the synthesis of a variety of chemicals and pharmaceuticals.
It is also known as 3,5-DBP or pyridino-2,3-dibromide.
Synthesis of 3,5-dibromo-2(1H)-pyridinone
3,5-dibromo-2(1H)-pyridinone can be synthesized through several methods.
One common method involves the reaction of 2-bromopyridine with 3-bromopropionyl chloride in the presence of a base such as sodium hydroxide.
The reaction proceeds through an SN2 mechanism, with the pyridine ring being the substrate.
Another method involves the reaction of 2-chloropyridine with 3-bromopropionyl chloride in the presence of a base such as triethylamine.
This method is also an SN2 reaction, with the pyridine ring again acting as the substrate.
Uses of 3,5-dibromo-2(1H)-pyridinone
3,5-dibromo-2(1H)-pyridinone is an important intermediate in the synthesis of several chemicals and pharmaceuticals.
One common use is in the production of the antibiotic erythromycin.
The compound is also used in the production of pyridine derivatives, such as pyrimidine nucleotides and fluorescent brighteners.
3,5-dibromo-2(1H)-pyridinone can also be used as an insecticide and nematicide, as it interferes with the ability of nematodes to excrete chitin, a key component of nematode cuticles.
This results in weakened nematodes that are unable to cause damage to crops.
Safety and handling
3,5-dibromo-2(1H)-pyridinone is generally considered to be a hazardous chemical.
It is highly toxic to aquatic organisms and can cause respiratory, dermal, and eye irritation in humans.
It is also a suspected carcinogen.
The handling of 3,5-dibromo-2(1H)-pyridinone should be done with caution and in accordance with the appropriate safety protocols.
This includes wearing appropriate personal protective equipment, such as gloves and protective eyewear, and working in a well-ventilated area.
Storage of 3,5-dibromo-2(1H)-pyridinone
3,5-dibromo-2(1H)-pyridinone should be stored in a cool, dry place and protected from moisture and sunlight.
It should be stored away from sources of ignition and from incompatible materials such as oxidizing agents.
Regulations and legal considerations
3,5-dibromo-2(1H)-pyridinone is considered a hazardous chemical and is subject to various regulations and legal considerations.
It is classified as a Category 2 carcinogen under the Canadian Environmental Protection Act, and is also regulated by the United States Environmental Protection Agency (EPA) and the European Chemicals Agency (ECHA).
Conclusion
3,5-dibromo-2(1H)-pyridinone is an important intermediate in the synthesis of a variety of chemicals and pharmaceuticals.
It is also used as an insecticide and nematicide.
The compound is generally considered to be hazardous and appropriate safety protocols should be followed during its handling and storage.
It is also subject to various regulations and legal considerations.