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Dicyclohexylchlorophosphine is an organophosphorus compound with the chemical formula (C₆H₁₁)₂PCl, appearing as a colorless to pale yellow liquid or low-melting solid with a pungent odor, sensitive to moisture and air, requiring storage under inert conditions such as nitrogen or argon. It serves as a versatile reagent in synthetic chemistry, particularly in the preparation of phosphine ligands for transition metal catalysis due to its ability to coordinate with metals, forming stable complexes used in cross-coupling reactions, hydrogenation, and polymerization processes. The compound's chlorophosphine group is highly reactive, enabling nucleophilic substitutions to generate tertiary phosphines or phosphonium salts, which are valuable in asymmetric synthesis and material science.
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Its sterically bulky cyclohexyl groups enhance stability and influence the electronic properties of resulting metal complexes, making it useful in designing catalysts with tailored reactivity. Due to its moisture sensitivity, handling must occur in anhydrous environments, typically using Schlenk-line or glovebox techniques to prevent hydrolysis. Dicyclohexylchlorophosphine is also employed in the synthesis of flame retardants, agrochemicals, and specialty polymers, though its primary significance lies in organometallic and coordination chemistry, where it facilitates the development of efficient catalytic systems for industrial and research applications. Proper disposal and safety measures are essential due to its corrosive and toxic nature.Dicyclohexylchlorophosphine (DCP) is an organophosphorus compound with various applications.
1. Catalytic reaction
DCP is an important catalyst and catalyst precursor in catalytic reactions, especially showing excellent performance in hydrogen oxidation reactions. As a high-efficiency hydrogen oxidation reaction catalyst, it can effectively promote the hydrogen oxidation process of oxygen-containing organic compounds such as alcohols, ketones, and aldehydes, accelerating the conversion of reactants to target products with high selectivity and yield. For example, in the hydrogen oxidation reaction of acetophenone, DCP can specifically activate the carbonyl group in acetophenone molecules, promote the addition of hydrogen atoms, and efficiently convert acetophenone into phenylethyl alcohol-a key intermediate widely used in the fields of spices, pharmaceuticals, and fine chemicals.
In addition, DCP also serves as an efficient catalyst for the cracking reaction of α-alkylamides; it can break the amide bond in alkylamide molecules under mild reaction conditions, generating two kinds of alkyl compounds with high purity, which provides a simple and efficient synthetic route for the preparation of alkyl compounds. Furthermore, DCP can catalyze the alkylation reaction of benzyl alcohol and benzoic acid, promoting the substitution reaction between the hydroxyl group of benzyl alcohol and the carboxyl group of benzoic acid, and preparing benzyl benzoate with high yield, which is widely used in plasticizers, solvents, and other fields.
2. Organic synthesis
DCP occupies an important position in organic synthesis due to its strong reactivity and good regioselectivity, and it is widely used as a key reagent and intermediate in the synthesis of various organic compounds. It can act as an acylating agent and phosphorylating agent to participate in multiple types of organic reactions, efficiently synthesizing important organic compounds such as acid chlorides, esters, and amides. For instance, in the synthesis of acid chlorides, DCP can react with carboxylic acids under mild conditions, replacing the hydroxyl group in carboxylic acid molecules with chlorine atoms to generate corresponding acid chlorides, which are important intermediates for the synthesis of esters, amides, and other compounds.
In addition, DCP is prone to nucleophilic substitution reactions with other molecules due to the high electrophilicity of the phosphorus atom and the good leaving ability of the chlorine atom. When reacting with nucleophiles such as ammonia or thiourea, the chlorine atom in DCP is substituted by amino or thiourea groups, generating corresponding phosphorus-containing nucleophiles. These nucleophiles can further participate in subsequent organic synthesis reactions, providing diverse synthetic pathways for the preparation of complex organic molecules.
3. Medicine
The application of DCP in the medical field is mainly focused on the synthesis of biologically active compounds and pharmaceutical intermediates, providing important support for the research and development of new drugs. It can be used as a key reagent to synthesize a series of biologically active compounds with pharmacological effects, such as polyphenols. Polyphenols have significant antioxidant, anti-inflammatory, and anti-tumor activities, and are important active ingredients in many natural drugs and synthetic drugs. DCP can regulate the reaction selectivity in the synthesis process of polyphenols, ensuring the structural integrity and biological activity of the products.
In addition, DCP is an important intermediate for the preparation of many bioactive molecules such as nucleotides and phosphorylcholine. Nucleotides are the basic components of nucleic acids and play a key role in cell metabolism, genetic information transmission, and other processes; phosphorylcholine is an important component of cell membranes and has important applications in the treatment of cardiovascular diseases and neurological diseases. The use of DCP to prepare these intermediates has the advantages of mild reaction conditions, high yield, and low impurity content, which can effectively reduce the cost of drug research and development and production.
4. Electronic materials
With the rapid development of the electronic information industry, DCP has been widely applied in the field of electronic materials due to its excellent electrical and optical properties. It is an important key component in optoelectronic materials and can be used as a photosensitizer in optoelectronic devices or an electrolyte additive in solar cells. As a photosensitizer, DCP can effectively absorb light energy in a specific wavelength range, convert light energy into electrical energy, and improve the photoelectric conversion efficiency of optoelectronic devices such as organic light-emitting diodes (OLEDs) and photodetectors.
When used as an electrolyte additive in solar cells, DCP can improve the ionic conductivity of the electrolyte, enhance the stability of the electrode-electrolyte interface, and thus improve the photoelectric conversion efficiency and service life of solar cells. In addition, similar to its performance in organic synthesis, DCP can undergo nucleophilic substitution reactions with other molecules in the preparation process of electronic materials, generating nucleophiles such as ammonia or thiourea. These nucleophiles can be used to modify the surface of electronic materials, improve the compatibility and stability of materials, and further optimize the performance of electronic devices.
5. Preparation of Ionic Liquids
DCP is an important raw material for the preparation of ionic liquids, which are a new type of green, non-volatile, and high-stability fluid materials with broad application prospects in chemical synthesis, separation engineering, electrochemistry, and other fields. The process of preparing ionic liquids using DCP is simple and efficient, and the prepared ionic liquids have adjustable properties and high purity. Usually, in the preparation process, DCP will react with some organic anions (such as imidazole anions, pyridine anions, etc.) and combine with different cations (such as alkyl imidazolium cations, quaternary ammonium cations, etc.) to form stable ionic complexes, thereby preparing ionic liquids with different properties.
The ionic liquids prepared by DCP have the advantages of low melting point, high thermal stability, and good solubility, and can be customized according to specific application needs, which greatly expands the application range of ionic liquids in various fields.
In conclusion, DCP is a multifunctional organophosphorus compound with a wide range of applications. It can be used as a catalyst for catalytic reactions and participate in reactions such as hydrogen oxidation, cracking reactions, and alkylation reactions. In addition, DCP can also be used in organic synthesis, medicine, electronic materials and other fields, and can be used to prepare ionic liquids.
Dicyclohexylchlorophosphine ( DCP ) is an organophosphorus compound with a variety of applications. In this paper, various synthesis methods of DCP are introduced in detail from the aspects of epoxidation reaction, alkylation reaction, dehydrochlorination reaction and pyrophosphate esterification reaction.
Epoxidation reaction is one of the most commonly used methods for preparing DCP. Firstly, ethylene oxide was reacted with triacontrone to obtain the epoxidation product. Then, the epoxidation product was alkylated with tricyclohexyl ketone to obtain DCP.
The alkylation reaction method is also one of the important methods for preparing DCP. This method usually uses phosphorus tetrachloride and tricyclohexyl methanol as raw materials, and tricyclohexyl methanol is excessively added. In the reaction, phosphorus tetrachloride reacts with tricyclohexyl methanol first, and then reacts with tricyclohexyl methanol in the presence of the intermediate of tricyclohexyl methyl phosphite, and finally DCP product is obtained.
Dehydrochlorination reaction is also one of the important methods for preparing DCP. The method uses tricyclohexyl ketone as raw material and phosphorus trichloride as dehydrogenation agent. In the reaction, tricyclohexyl ketone and phosphorus trichloride were subjected to dehydrochlorination to form an intermediate of tricyclohexyl methyl phosphite, which was then reacted with excess tricyclohexyl methanol to form a DCP product.
Pyrophosphate esterification reaction is also one of the important methods for preparing DCP. In this method, alkyl phosphorus trioxide was used as raw material, and it was reacted with tricyclohexyl methanol, and then DCP was finally obtained by heating, dehydration and other steps.
The above four reactions are all effective methods for preparing DCP, which have their own advantages and disadvantages. For example, DCP products prepared by epoxidation method have high purity and yield, but need to use high-quality raw materials and catalysts ; pyrophosphorylation reaction requires proper temperature and time control, otherwise it is not easy to obtain high yield products.
In a word, the above methods have their own characteristics, and the appropriate method can be selected according to the actual needs. However, in practical applications, it is also necessary to pay attention to safe operations and follow relevant regulatory standards to ensure the safety and sustainability of the production process.
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Chemical Formula |
C12H22ClP |
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Exact Mass |
232 |
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Molecular Weight |
233 |
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m/z |
232 (100.0%), 234 (32.0%), 233 (13.0%), 235 (4.1%) |
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Elemental Analysis |
C, 61.93; H, 9.53; Cl, 15.23; P, 13.31 |
The molecular structure of DCP consists of three cyclohexyl groups and a chlorine atom and a phosphorus atom. In the DCP molecule, the electron arrangement of the phosphorus atom is sp3 hybridization, which forms a tetrahedral geometry. Because the chlorine atom has a relatively large atomic radius, the area around the three cyclohexyl groups around the phosphorus atom and the corner represented by the chlorine atom is tightly closed, forming a relatively angular shape.
In addition, the bond length between the phosphorus atom in the DCP molecule and the carbon atom in the cyclohexyl group tends to be shorter. This is because the electronegativity of the phosphorus atom is lower than that of the carbon atom, so that the covalent bond between the two atoms is more biased towards the carbon atom. In addition, there are C-H... Cl, P-H... Cl, C-H... P bonds in the molecule of DCP, and the formation of these bonds enhances the stability of the molecule.
Therefore, several main structural features of DCP molecules can be summarized :
Phosphorus (P) atoms are hybridized with sp3 in DCP molecules, forming a tetrahedral configuration. This configuration means that the valence layer electron pairs (including bonding electron pairs and lone pair electrons) of phosphorus atoms are distributed in a tetrahedral shape in space. In this case, the phosphorus atom is connected to three cyclohexyl groups (possibly through oxygen, carbon, or other atoms, depending on the exact structure of DCP) and one chlorine atom, forming four covalent bonds.
The chlorine atom, as a vertex of the tetrahedral configuration, has a larger atomic radius and higher electronegativity, which allows the DCP molecule to occupy a larger space in that direction, potentially resulting in a more angular appearance of the molecule as a whole. This shape not only affects the physical properties of the molecule, such as polarity and solubility, but may also affect its chemical reactivity.
3. Covalent bond between phosphorus atom and carbon atom:
The covalent bond formed between phosphorus atoms and carbon atoms in cyclohexyl groups usually has a shorter bond length, which may be due to the small difference in electronegativity between phosphorus and carbon, as well as the strong bond energy of the covalent bond formed between them. A shorter key length usually means stronger bonding and higher stability.
4. Non covalent interactions within molecules:
The bonds you mentioned, such as CH-Cl, PH-Cl, CH-P, etc., are not actually covalent bonds in the traditional sense, but rather non covalent interactions within the molecule, such as hydrogen bonds (if the hydrogen atom is close enough to electronegative atoms such as chlorine or phosphorus) or van der Waals forces (including dispersion, induction, and orientation forces). These interactions are crucial for maintaining the three-dimensional structure and stability of molecules.
However, it should be noted that not all mentioned combinations can form hydrogen bonds, as the formation of hydrogen bonds requires hydrogen atoms to be in close proximity to highly electronegative atoms such as fluorine, oxygen, and nitrogen.
The stability of DCP molecules is not only determined by the strength of their covalent bonds, but also significantly influenced by non covalent interactions within the molecule. These interactions help to reduce the total energy of molecules, thereby placing them in a more stable state. The structural characteristics of DCP molecules include the tetrahedral configuration of phosphorus atoms, the influence of chlorine atoms on molecular shape, the short covalent bonds between phosphorus and carbon, and the presence of various non covalent interactions within the molecule. These characteristics collectively determine the physical properties and chemical reactivity of DCP molecules. In summary, the structural characteristics of DCP molecules have an important influence on their physicochemical properties and biochemical reactions. Studying and mastering these characteristics will help to better understand the properties and applications of DCP, and also provide a theoretical basis for further research on Dicyclohexylchlorophosphine.
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