Shaanxi BLOOM Tech Co., Ltd. is one of the most experienced manufacturers and suppliers of (5-bromo-2-chlorophenyl)(4-fluorophenyl)methanone cas 915095-85-1 in China. Welcome to wholesale bulk high quality (5-bromo-2-chlorophenyl)(4-fluorophenyl)methanone cas 915095-85-1 for sale here from our factory. Good service and reasonable price are available.
(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 medicines 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.
Core Pharmaceutical Intermediates and Pharmacological Research Tools
In the pharmaceutical industry, this substance serves as a core intermediate for the R&D of central nervous system (CNS) medicines, anti-infective agents and kinase inhibitors. Sustained growth in global pharmaceutical R&D investment (exceeding 238 billion US dollars in 2023) has further driven the expansion of its market demand.
Synthesis of Central Nervous System medicines
The halogenated benzophenone skeleton exhibits high affinity for multiple neurotransmitter receptors such as serotonin and dopamine receptors. As a building block, this substance can be used to synthesize antidepressant, anxiolytic and antipsychotic medicines. Its bromine atom enables the introduction of heterocycles (e.g., pyridine, imidazole) via Suzuki-Miyaura coupling; the chlorine atom allows linkage with amino or hydroxyl groups through nucleophilic substitution; the fluorine atom enhances molecular lipophilicity and blood-brain barrier permeability, thereby improving the central targeting efficiency of medicines.
For instance, in the synthesis of selective serotonin reuptake inhibitors (SSRIs), this intermediate can be structurally modified in multiple steps to construct pharmacophores with high receptor matching, significantly boosting medicine potency and selectivity.
R&D of Anti-Infective medicines
The halogenated aromatic ring structure of the substance interferes with bacterial/fungal cell wall synthesis and nucleic acid replication, making it a vital precursor for the development of broad-spectrum antibiotics and antifungal agents.
Its ketone carbonyl group can be reduced to hydroxyl groups or converted into derivatives such as oximes and hydrazones to enhance inhibitory activity against medicine-resistant bacteria including MRSA. Bromine and chlorine substituents bind to the active sites of microbial enzymes through halogen bonding, strengthening antibacterial efficacy. In the synthesis of antifungalmedicines, cyclization of this intermediate constructs the core skeleton of azole antifungals, exerting potent inhibitory effects on fungi such as Candida and Aspergillus.
Research on Kinase Inhibitors and Antitumor medicines
As a key building block for synthesizing multi-target kinase inhibitors, the substance is applicable to the preparation of antitumor medicines targeting epidermal growth factor receptor (EGFR) and vascular endothelial growth factor receptor (VEGFR). Its dihalogen substitution pattern mimics hydrogen bonding and hydrophobic interactions in the ATP-binding domain of kinases. Structural modification optimizes the selective killing effect on tumor cells and reduces toxic and side effects. In antitumor medicine R&D, coupling reactions of this intermediate introduce chemotherapeutic molecules or targeted carriers to construct targeted antitumor prodrugs, increasing medicine enrichment in tumor tissues.
Research on medicine Metabolism and Pharmacological Mechanisms
This substance can be used as a probe molecule to investigate medicine metabolic pathways and action mechanisms. Its isotopically labeled derivatives (e.g., bromine-77Br, fluorine-18F) can trace the absorption, distribution, metabolism and excretion (ADME) processes of medicines in vivo. The halogenated aromatic ring simulates interactions between medicines and metabolic enzymes such as CYP450, providing a basis for optimizing medicine metabolic stability.
Optoelectronic Materials and Polymer Additives
In the field of organic functional materials, benefiting from its conjugated benzophenone structure and polyhalogen substitution characteristics, the substance holds important application value in optoelectronic materials, polymer additives and liquid crystal materials.
Organic Optoelectronic Materials
It is a key building block for synthesizing organic light-emitting diode (OLED) and organic photovoltaic (OPV) materials. Its conjugated structure enables electron delocalization and favorable charge transport performance. The strong electron-withdrawing effect of fluorine atoms modulates material energy level structure, improving electron transport efficiency and photostability.In OLED materials, polymerization or coupling of this intermediate constructs blue/green light-emitting layer materials featuring high luminous efficiency, excellent color purity and long service life.
In OPV materials, it serves as a synthetic precursor for electron acceptor materials to enhance the energy conversion efficiency of photovoltaic devices.
Polymer Material Additives
The substance acts as a light stabilizer, flame retardant and antioxidant for polymer materials, improving weather resistance, flame retardancy and thermal stability. Its halogenated aromatic ring absorbs ultraviolet rays to suppress photodegradation of polymers.
bromine and chlorine substituents exert a synergistic flame-retardant effect by releasing halogen radicals during combustion, interrupting chain combustion reactions and reducing burning rate and smoke density. Incorporation of this substance into plastics, rubber, coatings and other polymers significantly extends service life and improves application safety.
Liquid Crystal Materials
The rod-shaped molecular structure and conjugated system meet the structural requirements of liquid crystal molecules, making it an important intermediate for new liquid crystal material synthesis.
Fluorine atoms adjust the liquid crystal phase temperature range and dielectric anisotropy; bromine and chlorine substituents enhance chemical and thermal stability. In the synthesis of nematic and smectic liquid crystals, etherification and esterification of this intermediate build the core liquid crystal skeleton. The prepared liquid crystal materials feature fast response speed, high contrast ratio and wide operating temperature range, applicable to the manufacture of liquid crystal displays, liquid crystal sensors and other devices.
Reagents, Catalysts and Synthetic Building Blocks
In analytical chemistry and scientific research, the substance functions as a chromatographic derivatization reagent, organic synthesis catalyst ligand and research-grade synthetic building block, widely applied in substance separation, structural analysis and organic synthesis methodology research.
Chromatographic Analytical Reagents
It serves as a derivatization reagent for high-performance liquid chromatography (HPLC) and gas chromatography (GC), derivatizing polar substances such as alcohols, phenols, amines and carboxylic acids to improve chromatographic separation efficiency and detection sensitivity. Its halogenated aromatic ring forms stable derivatives with polar substances, increasing retention on chromatographic columns; fluorine atoms enhance the volatility and thermal stability of derivatives, making it suitable for GC analysis.
In the detection of medicines, environmental pollutants and biological samples, this derivatization reagent enables efficient separation and high-sensitivity detection of trace polar substances.
Ligands for Organic Synthesis Catalysts
The substance acts as a ligand for transition metal catalysts (e.g., palladium, ruthenium, rhodium complexes), catalyzing organic synthesis reactions including Suzuki-Miyaura coupling, Heck reaction and hydrogenation.
Its ketone carbonyl and halogen atoms form stable coordination bonds with transition metal ions, regulating the electronic effect and steric hindrance of catalysts to enhance catalytic activity, selectivity and stability. In the synthesis of complex natural products and medicine molecules, it facilitates efficient and highly selective construction of carbon-carbon and carbon-heteroatom bonds, shortening synthetic routes and reducing production costs.
Research-Grade Synthetic Building Blocks
It is an essential building block for organic synthesis methodology research and substance library construction, widely used in universities, research institutes and CRO companies. Multiple reactive sites (bromine, chlorine, fluorine, ketone carbonyl) participate in diverse organic reactions, enabling rapid construction and diversified modification of molecular skeletons.
Its high purity (≥97%) and commercial availability (supplied by Combi-Blocks, Sigma-Aldrich and other vendors) facilitate scientific research. In combinatorial chemistry and diversity-oriented synthesis, this core building block rapidly constructs structurally diverse substance libraries for medicine screening and bioactivity evaluation, accelerating new medicine discovery.
Other Application Fields
Beyond the above major sectors, the substance also has potential application value in perfume synthesis, dye industry and environmental science. In perfume synthesis, it acts as an intermediate to prepare halogenated aromatic fragrances with unique aroma and long-lasting scent retention. In the dye industry, it synthesizes high-performance disperse dyes and reactive dyes to improve light fastness and wash fastness. In environmental science, it is used as a standard reference material and degradation intermediate for environmental pollutants, supporting pollutant detection and degradation mechanism research and providing technical support for environmental pollution remediation.
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 substances 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 substance will continue to play a pivotal role in driving chemical innovation.
This compound is predominantly synthesized using 5-bromo-2-chlorobenzoic acid as the starting material via two core steps: chlorination of carboxylic acid and Friedel-Crafts acylation. The process features mature technology, high selectivity and easy impurity control, with an overall yield of 75%-85%.
Acid Chlorination Reaction: Dissolve 5-bromo-2-chlorobenzoic acid in dichloromethane, add thionyl chloride dropwise at a controlled temperature of 0-10℃, and conduct reflux reaction for 3-5 hours to produce 5-bromo-2-chlorobenzoyl chloride. After the reaction, concentrate under reduced pressure to remove excess thionyl chloride and solvent, obtaining an acyl chloride concentrate that can be directly used in the next step without further purification.
Friedel-Crafts Acylation Reaction: Mix fluorobenzene with dichloromethane, add anhydrous aluminum trichloride as a catalyst, and slowly dropwise add the above acyl chloride concentrate at 5-15℃. After dropping completion, raise the temperature to 25-35℃ and stir for 6-8 hours. Upon full reaction monitored by TLC, pour the reaction mixture slowly into ice water for quenching.
Separate the layers, extract the aqueous phase with dichloromethane, combine all organic phases, wash sequentially with water and 5% sodium bicarbonate solution, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain the crude product.
Purification: Recrystallize the crude product from isopropanol, followed by cooling crystallization, centrifugal separation and vacuum drying at 40-50℃ to afford the target product as a white solid with purity ≥98%. The content of ortho-isomer is ≤0.38% and unreacted raw material ≤0.04%. With low impurity levels, the product meets the quality standards for pharmaceutical and pesticide intermediates.
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