What are the chemical properties of 2-bromo-4-trifluoromethoxy-1-iodobenzene?
2-Bromo-4-trifluoromethoxy-1-iodobenzene is a class of organohalogenated aromatic hydrocarbons. It has unique chemical properties and is widely used in the field of organic synthesis.
First of all, its halogen atom activity. This compound contains two halogen atoms of bromine and iodine. The iodine atom is relatively small because of its large atomic radius and C-I bond energy. Therefore, in the nucleophilic substitution reaction, the iodine atom is easily attacked and left by the nucleophilic reagent, showing high reactivity. For example, under suitable conditions with sodium alcohol, the iodine atom is replaced by an alkoxy group to obtain the corresponding aromatic ether compound. Although the reactivity of bromine atom is slightly inferior to that of iodine atom, it can also participate in nucleophilic substitution under specific conditions. For example, when reacting with amines, nitrogen-containing aryl derivatives can be prepared.
The influence of trifluoromethoxy is described below. Trifluoromethoxy has strong electron absorption and can reduce the electron cloud density of the benzene ring. This electronic effect causes the activity of the electrophilic substitution of the benzene ring to decrease, and makes the electrophilic reagents more inclined to attack the position with relatively high electron cloud density on the benzene ring. At the same time, the existence of trifluoromethoxy can significantly change the physical properties of compounds, such as improving their fat solubility. In the field of medicinal chemistry, it helps drug molecules to pass through the biofilm
Furthermore, this compound can be used as a synthetic intermediate to construct complex organic molecular structures through multi-step reactions. Through metal-catalyzed coupling reactions, such as Suzuki coupling, Stille coupling, etc., it can react with substrates containing borate esters, tin reagents, etc., to achieve the construction of carbon-carbon bonds, expand the substituents on the benzene ring, and prepare organic materials or bioactive molecules with specific functions.
In conclusion, the atomic activity of 2-bromo-4-trifluoromethoxy-1-iodobenzene halogen, the electronic effect of trifluoromethoxy and its intermediate properties are of great value in many fields such as organic synthesis, drug development, and materials science. Chemists can skillfully design reaction routes according to their properties to create diverse and useful compounds.
What are the common synthetic methods of 2-bromo-4-trifluoromethoxy-1-iodobenzene?
The common synthesis methods of 2-bromo-4-trifluoromethoxy-1-iodobenzene are covered by the following numbers.
First, the nucleophilic substitution reaction is carried out using halogenated aromatics as the starting material. First, take a halogenated benzene containing an appropriate substituent, such as 2-bromo-4-chlorobenzene, and meet the trifluoromethoxylation reagent. The common use of this reagent is potassium trifluoromethoxy or sodium trifluoromethoxy. In a suitable solvent, such as N, N-dimethylformamide (DMF) or dimethylsulfoxide (DMSO), heat and stir to replace the chlorine atom with trifluoromethoxy to obtain 2-bromo-4-trifluoromethoxylbenzene. Then, this product is used as a substrate and reacted with an iodine-substituted reagent, such as iodine elemental (I ²) and an appropriate oxidant, such as cerium ammonium nitrate (CAN), under suitable conditions to introduce iodine atoms at designated positions on the benzene ring to obtain 2-bromo-4-trifluoromethoxy-1-iodobenzene.
Second, cross-coupling reaction catalyzed by palladium. First, borate esters or boric acid compounds containing trifluoromethoxy are prepared, and 2-bromo-1-iodobenzene is combined in a palladium catalyst, such as tetra (triphenylphosphine) palladium (Pd (PPh)), in an alkaline environment and a suitable solvent. The base can be selected from potassium carbonate, sodium carbonate, etc., and the solvent is usually a mixed system of toluene, dioxane and water. During the reaction, the temperature, reaction time and other conditions are controlled to couple the two to obtain the target product 2-bromo-4-trifluoromethoxy-1-iodobenzene.
Or, starting with the benzene ring, the substituents are gradually introduced. First, the benzene is trifluoromethoxylated, and the trifluoromethoxy group can be introduced into the benzene ring by a suitable trifluoromethoxylation reagent through a Friedel-Crafts reaction or other electrophilic substitution means. After that, the bromination and iodization reactions are carried out in sequence, and the corresponding halogenating reagents, such as bromine (Br ²) and iodine reagents, are introduced into the bromine atom and iodine atom in the desired position under suitable catalyst and reaction conditions to synthesize 2-bromo-4-trifluoromethoxy-1-iodobenzene.
In what areas is 2-bromo-4-trifluoromethoxy-1-iodobenzene applied?
2-Bromo-4-trifluoromethoxy-1-iodobenzene is an organic compound that has applications in various fields.
In the field of medicinal chemistry, this compound can be used as an important intermediate. In the process of covering organic synthesis, its unique chemical structure can participate in a variety of key reactions through the reactivity of halogenated groups and trifluoromethoxy groups. Such as nucleophilic substitution reactions, which can replace bromine or iodine atoms with suitable nucleophiles to form new carbon-heteroatomic bonds to generate compounds with potential biological activities or to synthesize complex drug molecules.
In the field of materials science, 2-bromo-4-trifluoromethoxy-1-iodobenzene is also possible. Due to the introduction of trifluoromethoxy, the molecule is endowed with special physical and chemical properties, such as improving the solubility, thermal stability and hydrophobicity of the molecule. Therefore, it may be applied to the preparation of new functional materials, such as in organic optoelectronic materials, by participating in the reaction, the electron transport properties and optical properties of the material can be optimized, and then the efficiency and stability of organic Light Emitting Diode (OLED) or organic solar cells can be improved.
Furthermore, this compound also has potential value in pesticide chemistry. Its special structure or imparts certain biological activity, which can be optimized as a lead compound. By modifying its structure and exploring its interaction with biological targets, it is expected to develop new pesticides with high efficiency, low toxicity and environmental friendliness to meet the needs of crop disease and insect control.
In summary, 2-bromo-4-trifluoromethoxy-1-iodobenzene has shown broad application prospects in many fields such as medicine, materials and pesticides with its unique structure, providing an important material basis for innovation and development in various fields.
What are the physical properties of 2-bromo-4-trifluoromethoxy-1-iodobenzene?
2-Bromo-4-trifluoromethoxy-1-iodobenzene is a very important compound in the field of organic synthesis. Its physical properties are unique and have a great impact on the reaction process and product characteristics of organic synthesis.
Looking at its properties, under normal temperature and pressure, this compound is mostly colorless to light yellow liquid, with a clear appearance and a certain fluidity. This morphology is determined by the intermolecular force. The intermolecular force is moderate, and the molecules are not tightly packed into a solid state, nor are they vaporized due to too weak force.
When it comes to melting point and boiling point, the melting point is usually in a relatively low range, about - [X] ° C. The characteristic of this low melting point is due to the spatial arrangement and electronic effect of bromine, iodine and trifluoromethoxy groups in the molecular structure, which hinders the orderly arrangement of molecules to form a tight lattice, resulting in a decrease in lattice energy and melting point. The boiling point is relatively high, about [X] ° C. Because the molecule contains halogen atoms and polar trifluoromethoxy groups, there is a strong dipole-dipole force between molecules, and more energy is required to gasify it, so the boiling point rises.
Its density is greater than that of water, about [X] g/cm ³. This is because the relative atomic weight of bromine and iodine atoms in the molecule is larger, resulting in an increase in the mass of the substance per unit volume. The compound is insoluble in water, but easily soluble in common organic solvents such as dichloromethane, chloroform, and ether. This difference in solubility is due to the fact that water is a strong polar solvent, while 2-bromo-4-trifluoromethoxy-1-iodobenzene contains polar groups, but the overall molecular polarity is not enough to form a strong interaction with water, and it is similar to the polarity of organic solvents. According to the principle of "similar miscibility", it is easily soluble in organic solvents.
In addition, this compound has a certain volatility, which can be slowly volatilized in air, and has a certain pungent odor because it contains halogen atoms. When operating, it is necessary to pay attention to a well-ventilated environment to prevent damage to the human body.
What is the market price of 2-bromo-4-trifluoromethoxy-1-iodobenzene?
I don't know what the market situation is for 2-bromo-4-trifluoromethoxy-1-iodobenzene. This compound is not an ordinary thing, and its market situation is very common due to many reasons.
First, its cost is easy to do. If you need complex work and rare raw materials, the cost will be high, and the market will be self-sufficient. This compound contains special bases, such as trifluoromethoxy, and the synthesis of it requires special materials, and the cost will rise as a result.
Second, the supply and demand of the market also affects its cost. If a certain field, such as research and material science, has strong demand and limited supply, the price will be high. On the contrary, if there is little demand, the supply will be full, and the price will drop.
Third, the difference in suppliers also makes the price different. Different suppliers have different levels depending on the cost of production, technology level, and strategy.
If you want to know the market, you can go to the supply platform, such as Alfa Aesar (Alfa Aesar), Tixi (TCI), etc., or the transformation of the supplier, you can get the price.