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(5-bromo-2-chlorophenyl)(4-fluorophenyl)methanone, also known as (2-chloro-5-bromophenyl) (4-fluorophenyl) ketone; 3- (4-fluorophenylketone) -1-bromo-4-chlorophenyl is a chemical substance that is a white powder. High purity products can usually reach over 99%, and are stable at room temperature and pressure, but avoid contact with strong oxidants, strong acids, strong bases, etc. Can participate in various organic chemical reactions. It can be used as an intermediate of anti diabetes drugs such as engegliptin, and can also be used to synthesize other organic compounds.
Additional information of chemical compound:
|
Chemical Formula |
C13H7BrClFO |
|
Exact Mass |
311.94 |
|
Molecular Weight |
313.55 |
|
m/z |
311.94 (100.0%), 313.93 (97.3%), 313.93 (32.0%), 315.93 (31.1%), 312.94 (14.1%), 314.94 (13.7%), 314.94 (4.5%), 316.93 (4.4%) |
|
Elemental Analysis |
C, 49.80; H, 2.25; Br, 25.48; Cl, 11.31; F, 6.06; O, 5.10 |
|
Boiling point |
390.6±37.0 °C(Predicted) |
|
Density |
1.568±0.06 g/cm3(Predicted) |
|
Storage conditions |
2-8℃ |
(5-bromo-2-chlorophenyl)(4-fluorophenyl)methanone, also known as 3- (4-fluorophenyl ketone) yl-1-bromo-4-chlorophenyl or empagliflozin intermediate, is mainly used as a pharmaceutical intermediate, especially playing a key role in the synthesis of empagliflozin. The following is a detailed explanation of its purpose:
1.Pharmaceutical intermediates
The synthesis of empagliflozin
- It is an important intermediate in the synthesis process of empagliflozin. Enggliptin is a drug used to treat type 2 diabetes. It belongs to SGLT2 (sodium glucose cotransporter 2) inhibitor and can help patients reduce blood sugar levels.
- Through specific chemical reaction, the intermediate can be converted to engegliptin, which can be further used in the treatment of diabetes.
Other medicinal uses
In addition to serving as an intermediate in the synthesis of empagliflozin, it may also play important roles in other pharmaceutical synthesis processes, but its specific application areas and drugs have not been widely disclosed.
2.Scientific research
- Chemical synthesis research: Due to its unique chemical structure and properties, it also has certain research value in the field of chemical synthesis. Scientists can use it as a raw material or intermediate for synthesizing other organic compounds, further exploring new chemical reactions and synthetic pathways.
- Drug development: In the field of drug development, this intermediate may serve as a starting point or one of the key steps in the development of new drugs. By chemically modifying or optimizing its structure, scientists can develop new drugs with better efficacy and lower side effects.
3.Industrial applications
Chemical production
In chemical production, it can be used as a raw material or additive for the production of other chemicals. These chemicals may be widely used in industrial fields such as coatings, plastics, rubber, etc.
Environmental Protection and Water Treatment
Although the direct application of this intermediate in environmental protection and water treatment has not been widely reported, given its chemical properties and structural characteristics, it may play an important role in this field in the future. For example, it can serve as an adsorbent or catalyst for a specific pollutant.
► Agrochemical Synthesis
1) Herbicides
Sulfonylurea Herbicides: Derivatives of (5-bromo-2-chlorophenyl)(4-fluorophenyl)methanone inhibit acetolactate synthase (ALS), a key enzyme in branched-chain amino acid synthesis in plants.
Example: Chlorsulfuron analogs, where the ketone is functionalized with a sulfonylurea group.
2) Fungicides
Strobilurin Analogues: Mimic natural strobilurins to disrupt mitochondrial respiration in fungi. The halogenated phenyl groups enhance membrane permeability and stability.
► Materials Science
1) Organic Electronics
Hole-Transport Materials (HTMs): Used in organic light-emitting diodes (OLEDs) and perovskite solar cells, the compound's electron-deficient aromatic rings facilitate hole injection and transport.
Liquid Crystals: Halogenated ketones improve the mesogenic properties (e.g., nematic phase stability) of liquid crystal displays (LCDs).
2) Coordination Chemistry
Ligand Design: The ketone oxygen and halogen atoms can coordinate to transition metals (e.g., Pd, Pt), forming complexes with catalytic or luminescent properties.
What are the side effects?
As a synthetic intermediate of Empagliflozin, its side effects are mainly related to Empagliflozin and its SGLT2 inhibitor drugs,Its side effects include:
- Fungal infections in the reproductive system: SGLT2 inhibitors increase the risk of reproductive tract infections in patients, especially fungal genital infections.
 |
Urinary system infection: Because SGLT2 inhibitors lead to significant diabetes, especially in patients with type 2 diabetes, the risk of urinary tract infection increases. |
- Insufficient capacity: SGLT2 inhibitors may cause patients to experience insufficient capacity.
- Ketoacidosis: The causal relationship between SGLT2 inhibitors and ketoacidosis is not yet clear, and the incidence is also very low.
- Risk of lower limb amputation: Some studies have found that the use of SGLT2 inhibitors may increase the risk of lower limb amputation, although this has not been confirmed in other studies.
| Hypoglycemia: Although SGLT2 inhibitors are not associated with an increase in hypoglycemic events when used alone, hypoglycemia may occur when used in combination with sulfonylureas or insulin. |  |
What are the safety and danger?
1.Safety
- As a pharmaceutical intermediate, the safety of this compound mainly focuses on its potential risks during synthesis and use. Although it is not directly used for human treatment, it may produce certain harmful substances or reactions when synthesizing drugs. Therefore, in the synthesis and use process, chemical safety and environmental regulations should be strictly followed to ensure the safety and environmental protection of the production process.
2.Storage conditions
To ensure the quality and stability of (5-bromo-2-chlorophenyl)(4-fluorophenyl)methanone, specific storage conditions need to be followed:
- Temperature: It should be stored in a low temperature environment of 2-8 ° C to maintain its chemical stability.
- Moisture proof: This compound is sensitive to moisture, so it should be stored in a dry environment to avoid dampness.
- Avoid light: Long term exposure to sunlight may cause compounds to decompose or deteriorate, so they should be stored in a dark environment.
- Sealing: Store in a sealed container to prevent air and moisture from entering, while also helping to maintain the purity of the compound.
What is an intermediate of empagliflozin
Empagliflozin intermediate refers to a compound that participates in chemical reactions as a raw material or reactant in the synthesis of Empagliflozin, and is ultimately converted into empagliflozin or its active form. It is a SGLT2 inhibitor for the treatment of type 2 diabetes. The following is a detailed explanation of the intermediate of engegliptin:
1.Definition and Classification
Definition
The intermediate of empagliflozin is a key raw material for the synthesis of empagliflozin, which plays a bridging role in chemical reactions and gradually transforms into empagliflozin through a series of chemical reactions.
Classification
According to the different chemical structures and synthesis pathways, there can be various types of intermediates of empagliflozin, such as (5-bromo-2-chlorophenyl)(4-fluorophenyl)methanone, etc.
2.Function and Importance
- Function: The intermediate of empagliflozin plays a role in constructing the drug skeleton, introducing active or functional groups, and adjusting the physicochemical properties of the drug during the synthesis process.
- Importance: High quality intermediates are the foundation for synthesizing efficient, safe, and stable drugs. The purity and structural stability of intermediates directly affect the efficacy and safety of the final drug.
3.Storage and transportation
Storage conditions
The intermediate of empagliflozin usually needs to be stored under specific temperature and humidity conditions to ensure its chemical stability and prevent degradation.
Transportation requirements
During transportation, corresponding measures need to be taken to maintain the quality and stability of the intermediate, such as avoiding light, moisture, heat, etc.
4.Safety and Environmental Protection
- Safety: The intermediate of empagliflozin may have certain toxicity and danger, so it is necessary to strictly follow relevant safety operating procedures and protective measures during synthesis and use.
- Environmental friendliness: In the process of synthesizing empagliflozin, efforts should be made to minimize the emission and waste of harmful substances, improve resource utilization, and properly dispose of waste to protect the environment and ecology.
5.Market and Application
- Market: With the widespread application of empagliflozin in the global market, the demand for empagliflozin intermediates is also constantly increasing. Therefore, many professional intermediate manufacturers and suppliers have emerged in the market.
- Application: The intermediate of empagliflozin is mainly used in the field of pharmaceutical synthesis and is a key raw material for the synthesis of empagliflozin, a new type of hypoglycemic drug.
Using brown glass bottles
Brown glass bottles have a strong ability to absorb light, which can effectively reduce the impact of light on chemical reagents.
Wrap with black paper for external use
Wrap a layer of black paper around the brown glass bottle to further enhance the light shielding effect and ensure that the reagent is not affected by light during storage.
Store in a dark room or a light shielded reagent cabinet
Placing brown glass bottles containing reagents in a dark room or a specially designed light shielded reagent cabinet can prevent external light from directly shining on the reagents.
Avoid direct sunlight
During storage and transportation, it should be ensured that the reagents are not exposed to direct sunlight to prevent chemical reactions caused by light, which can lead to deterioration of the reagents.
Recent Advances and Future Trends
► Green Chemistry Innovations
Solvent-Free Synthesis: Ball milling enables Friedel-Crafts acylation without DCM, reducing waste.
Biocatalysis: Lipase-catalyzed acylation in water/ionic liquid mixtures offers milder conditions.
► High-Value Derivatives
Trifluoromethyl Ketones: Demand for CF₃-substituted analogs is rising in antifungal drug development.
Chiral Ketones: Enantioselective synthesis via asymmetric hydrogenation enables stereospecific drugs.
► Market Dynamics
Regional Growth: Asia-Pacific dominates production (55% market share), driven by agrochemical demand in China and India.
Price Trends: Raw material costs (e.g., bromine, fluorine) and regulatory pressures on halogenated compounds influence pricing.
(5-Bromo-2-chlorophenyl)(4-fluorophenyl)methanone is a cornerstone of modern organic synthesis, bridging pharmaceuticals, agrochemicals, and advanced materials. Its reactivity, derived from the strategic placement of halogen atoms, enables the construction of complex molecules with tailored properties. While traditional synthesis methods remain dominant, the shift toward sustainable practices-such as biocatalysis and flow chemistry-promises to reduce environmental impact. As the global demand for innovative therapeutics and eco-friendly agrochemicals grows, this compound will continue to play a pivotal role in driving chemical innovation.
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