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What is the use of 6 - morpholin - 4 - yl - pyridineboronic acid
6 - (4 - morpholinyl) pyridine-boronic acid, which has a wide range of uses. In the field of medicinal chemistry, it can be used as a key organic synthesis intermediate for the creation of many new drugs. Due to its unique structure, it can precisely bind to specific targets in organisms, helping to develop anti-cancer, anti-infection and neurological disease therapeutics.
In the field of materials science, it has shown important value in the preparation of functional materials. For example, the preparation of materials with special optical and electrical properties, or the preparation of sensor materials with high sensitivity to specific substances, through which it interacts specifically with the target substance to achieve sensing detection.
In organic synthetic chemistry, 6- (4-morpholino) pyridine-boronic acid is a key building block for the construction of complex pyridine compounds. Through various coupling reactions, such as the Suzuki-Miyaura reaction, it can react efficiently with halogenated aromatics and other substrates to synthesize organic compounds with diverse structures and special properties, providing organic synthesis chemists with rich structural modification methods to create organic molecules with novel structures and properties.
What are the synthesis methods of 6 - morpholin - 4 - yl - pyridineboronic acid
To prepare 6- (morpholine-4-yl) pyridyl boronic acid, the common synthesis methods are as follows:
6-halopyridine can be selected as the starting material, such as 6-bromopyridine or 6-chloropyridine. Taking 6-bromopyridine as an example, a boric acid group can be introduced by a metal-mediated reaction.
First, at a low temperature (e.g. -78 ° C) and in an anhydrous and oxygen-free environment, 6-bromopyridine is reacted with n-butyl lithium to generate a corresponding lithium reagent. This reaction needs to be carried out under the protection of an inert gas (such as nitrogen or argon). n-butyl lithium will capture the hydrogen atom of the bromine atom ortho-position in 6-bromopyridine to form a more active carbon negative ion intermediate.
Subsequently, a borate ester, such as trimethyl borate or triisopropyl borate, is added to the system. The lithium reagent will undergo a nucleophilic substitution reaction with the borate ester to form a 6- (morpholine-4-yl) pyridine borate intermediate.
After the reaction is completed, the target product 6- (morpholine-4-yl) pyridyl boronic acid can be obtained by treating the borate ester intermediate under acidic conditions (such as dilute hydrochloric acid) through a hydrolysis step.
Another method can utilize a palladium-catalyzed coupling reaction. The reaction is carried out in the presence of a palladium catalyst (such as tetra (triphenylphosphine) palladium), a ligand (such as tri-tert-butyl phosphine), and a base (such as potassium carbonate) using 6-halopyridine, morpholine, and borate pinacol esters as raw materials. Palladium catalyst can activate the carbon-halogen bond of halogenated pyridine to couple with boronate pinacol ester, and morpholine also participates in the reaction, and finally produces 6- (morpholine-4-yl) pyridineboronate pinacol ester, and then hydrolyzes to obtain the target product.
In this synthesis process, the reaction conditions need to be strictly controlled, and the anhydrous and anaerobic environment is particularly critical for the reaction involving lithium reagents or palladium catalysis. And the proportion of materials, reaction temperature and time in each step of the reaction will affect the yield and purity of the product, which needs to be carefully regulated.
What are the physical properties of 6 - morpholin - 4 - yl - pyridineboronic acid
6 + - morpholin + - 4 + - yl + - pyridineboronic acid, that is, 6-morpholine-4-ylpyridineboronic acid, the physical properties of this substance are related to its appearance, melting point, solubility and other characteristics.
Looking at its appearance, under normal temperature and pressure, it is often white to light yellow solid powder with fine texture. This state is easy to store and use, and can provide convenience for subsequent experimental operations.
As for the melting point, it has been determined by many experiments to be between 135-140 ° C. As an important physical constant of a substance, the melting point can help to distinguish its purity. If the sample purity is high, the melting point is close to this range; if it contains impurities, the melting point may decrease and the melting range becomes wider.
In terms of solubility, the substance has a certain solubility in common organic solvents such as dichloromethane, N, N-dimethylformamide (DMF). In dichloromethane, due to the non-polar and molecular structure of dichloromethane, 6-morpholine-4-ylpyridyl boric acid can be moderately dissolved to form a uniform dispersion system; in DMF, its solubility is better due to the strong polarity and good solvation ability of DMF. However, the solubility in water is relatively small, because its molecular structure contains hydrophobic groups, and the interaction between water molecules is weak, only slightly soluble in water.
In addition, the density of the substance is about 1.31 g/cm ³, which is of great significance for operations such as accurate weighing and calculating the proportion of reactive materials. It is relatively stable in air, but it is exposed to humid environments or high temperatures for a long time, or deteriorates due to reactions such as hydrolysis. Therefore, it needs to be stored in a dry and cool place to prevent its physical properties from changing and affecting subsequent use efficiency.
What are the chemical properties of 6 - morpholin - 4 - yl - pyridineboronic acid
6 - (morpholine-4 -yl) pyridyl boronic acid is an important reagent in organic synthesis. Its chemical properties are unique, let me tell you one by one.
This compound has a boric acid group, which has remarkable properties. Boric acid can react with many nucleophiles, such as alcohols, under appropriate conditions, to form borate esters. This reaction is commonly used in organic synthesis to prepare compounds with specific structures. The formation of borate esters can change the polarity and reactivity of molecules, which in turn can help the subsequent reaction to carry out.
And because of the pyridine ring, the pyridine ring is aromatic and basic. The aromaticity makes the compound structurally stable, and the basicity allows the nitrogen atom of the pyridine ring to interact with acids or electrophilic reagents. And the pyridine ring can participate in various cyclization reactions, construct complex cyclic compounds, and expand its application in the synthesis of various organic molecules.
The presence of morpholine groups also affects the properties of compounds. Moroline groups contain nitrogen and oxygen atoms, and have certain nucleophilic and coordination abilities. They can coordinate with metal ions to form metal complexes, which have potential uses in catalytic reactions. At the same time, morpholine groups affect the molecular spatial structure and electron cloud distribution, and have effects on the solubility and reaction selectivity of compounds. The various chemical properties of 6 - (morpholine - 4 - yl) pyridyl boronic acid provide rich possibilities for the research and application in the fields of organic synthesis, medicinal chemistry, etc., and help researchers create more compounds with unique functions.
What is the price range of 6 - morpholin - 4 - yl - pyridineboronic acid in the market?
"6 - (morpholine-4-yl) pyridyl boronic acid" is in the market, and its price range is difficult to determine. This is due to many reasons that cause its price to fluctuate.
First, the method and difficulty of preparing this product are related to its price. If its preparation requires complicated steps, rare raw materials, and exquisite skills, the cost must be high and the price is also high. If the preparation method is simple and the raw materials are widely available, the price may be low.
Second, the trend of supply and demand is also the main reason. If the market needs more of this product, but there are few producers, and the supply exceeds the demand, the price will rise. If the supply exceeds the demand, the producers will sell their products, or reduce the price to promote.
Furthermore, the price of raw materials also affects it. The price of raw materials is high, and the price of raw materials is also high; the price of raw materials falls, and the price of raw materials may fall.
Repeat, the difference in regions, the difference in taxes and fees, the cost of transportation and storage, etc., can cause this thing to be different in different places and at different times.
Today in the market, the price of "6- (morpholine-4-yl) pyridyl boronic acid" ranges from tens of yuan to hundreds of yuan per gram. However, this is only an approximate number, and the actual price depends on the specific quality, purchase quantity, and time of transaction. If you want to know the exact price, you can consult the chemical raw material supplier or explore the quotation of the chemical product trading platform to obtain the accurate number.