Dicyclohexylcarbodiimide powder (DCC), CAS 538-75-0, is a bifunctional crosslinking agent. It is a white, odorous crystal or slightly yellow transparent liquid with a low melting point. It is soluble in dichloromethane, tetrahydrofuran, acetonitrile, and dimethylformamide, but insoluble in water. The chemical formula is C13H22N2, and the cn=c=nc part of the molecule is not a planar structure, but an orthogonal arrangement, similar to propylene diene. It is a commonly used dehydrating agent in esterification, amidation and other reactions, and can also be used for the synthesis of anhydrides, aldehydes, ketones and isocyanates. DCC is one of the most commonly used activators, which can promote condensation reactions between amino acids and efficiently synthesize peptide chains. In Fmoc solid-phase synthesis, DCC activates carboxyl groups and promotes the formation of amide bonds between the carboxyl group of an amino acid and the amino group of another amino acid. DCC helps to form activated esters in ester synthesis, improving reaction efficiency and yield. Steglich esterification reaction is one of the most commonly used methods in DCC esterification reaction, usually carried out at room temperature, suitable for substrates with high steric hindrance or acid sensitivity.
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Chemical Formula |
C13H22N2 |
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Exact Mass |
206 |
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Molecular Weight |
206 |
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m/z |
206 (100.0%), 207 (14.1%) |
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Elemental Analysis |
C, 75.68; H, 10.75; N, 13.58 |
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Cyclohexylamine and cyclohexyl isonitrile are coupled to form DCC under the action of palladium acetate, iodine and oxygen, and the yield can reach 67%
Two molecules of cyclohexyl isocyanate were condensed to form DCC under the catalysis of op (mench2ch2) 3N, with a yield of 92%
Dicyclohexylurea reacts with arylsulfonyl chloride, potassium carbonate and benzyltrimethylammonium chloride (phase transfer catalyst) to produce DCC.
Dicyclohexyl thiourea method is produced by the reaction of cyclohexylamine and carbon disulfide to produce n, n'- dicyclohexyl thiourea, which is obtained by dehydrogenation.
Dicyclohexylamine urea method can also be obtained by reacting n, n'- dicyclohexylurea with phosphorus pentoxide in pyridine.
Make n, n 'one two ring base pulse
240 g (2.42 mol) of cyclohexylamine was refluxed with 60 g (1.00 mol) of urea in 480 ml of isoamyl alcohol for 20 hours. After cooling, filter out the crystal, wash it with ether, and dry it to obtain 200 grams of N, n 'dicyclohexyl dolphin, with a yield of 89%.
Preparation of dicyclohexyl carbodiimide
200 g (0.891 mol) of dicyclohexyl chloride and 300 g (1.574 mol) of toluene sulfonyl chloride were stirred in 600 ml of anhydrous pyridine at 70 ℃ for 1 hour. Pour the reactant into 1.5 kg crushed ice and extract with ether. Wash and dry the ether solution with water. Evaporate the ether, and evaporate the residue under reduced pressure. 152 grams (82%) of dicyclohexyl carbodiimide were obtained
Dicyclohexylcarbodiimide powder (DCC) is an important organic compound with a wide range of applications.
Organic synthesis
DCC is mainly used as a dehydrating agent in organic synthesis, especially in esterification and amidation reactions.
Esterification and amidation reactions:
DCC can efficiently promote dehydration condensation between carboxylic acids and alcohols or amines, forming ester or amide bonds. The reaction conditions are mild, and the synthesis yield is usually high.
In peptide synthesis, DCC is commonly used in the condensation reaction of amino acids to help form peptide bonds.
Other reactions:
DCC can also be used for the synthesis of anhydrides, aldehydes, ketones, and isocyanates. DCC is the simplest, gentlest reaction condition, and highest yield coupling reagent in the synthesis of acid anhydrides.
DCC can also catalyze reactions such as the conversion of thiourea to cyanoguanidine, demonstrating its versatility in organic synthesis.
Medical field
DCC has a wide range of applications in the pharmaceutical field and is an indispensable part of many drug synthesis processes.
Drug synthesis:
DCC is a good low-temperature biochemical dehydrating agent used for the synthesis and dehydration of amikacin and amino acids.
It is also used for the synthesis of peptides and nucleic acids, as well as the production of drugs such as vasopressin and cyclic adenosine monophosphate. In these reactions, DCC can effectively promote the condensation of carboxylic acids and amines, forming stable amide bonds.
Drug carrier:
DCC can be used to couple drug molecules with carrier proteins, improving drug targeting and stability. This coupling reaction helps to achieve precise drug release in the body and improve therapeutic efficacy.
Pesticide field
DCC also has certain applications in the field of pesticides, mainly used for synthesizing certain pesticide intermediates.
These intermediates can be further reacted to prepare pesticide products such as insecticides and herbicides. The efficient dehydration performance of DCC enables it to play an important role in these synthetic reactions.
Dye field
DCC can be used for the synthesis of dyes, helping to improve their color and fastness.
Through the dehydration of DCC, dye molecules with specific structures and properties can be synthesized to meet the demand for high-quality dyes in the dye industry.
Other fields
In addition to the aforementioned fields, DCC has a wide range of applications in health products, cosmetics, printing and dyeing, biologics, and other areas.
Health products and cosmetics:
DCC can be used to synthesize certain compounds with health benefits, as well as active ingredients in cosmetics.
Printing and dyeing, biological agents:
In the printing and dyeing industry, DCC can be used for dye fixation treatment to improve the wash and light resistance of dyes.
In the field of biologics, DCC can be used to synthesize certain biomolecules, such as proteins, nucleic acids, etc.
In addition, it is worth mentioning that DCC also has potential application prospects in lithium battery electrolyte additives. Although the application in this field has not yet been industrialized, once successful, it will greatly expand the market space of DCC.
Dicyclohexylcarbodiimide powder (DCC), as an important organic compound, has a wide range of applications in organic synthesis, pharmaceuticals, pesticides, dyes, and other fields. There are two main methods for its preparation: the reaction of cyclohexylamine with carbon disulfide and the reaction of dicyclohexylurea with trichloromethyl carbonate. The following is a detailed description of these two preparation methods:
Reaction of cyclohexylamine with carbon disulfide
1. Reaction conditions
Under specific conditions, cyclohexylamine reacts with carbon disulfide to form dicyclohexylthioperoxide, which is then dehydrogenated to obtain DCC. During this process, catalysts such as triethylbenzyl ammonium chloride (TEBA) or polyethylene glycol play a crucial role.
2. Reaction mechanism
Step 1: Cyclohexylamine reacts with carbon disulfide to form cyclohexyl thiourea and sodium sulfide.
Step 2: Under the oxidation of sodium hypochlorite, cyclohexyl thiourea undergoes secondary oxidation to remove hydrogen sulfide and generate DCC.
Step 3: Add sodium sulfide to the separated organic phase and react with sulfur to remove sulfur.
3. Advantages and disadvantages
advantage:
The product has high purity and yield.
Less by-products and strong operational reliability.
Sulfur will not remain in the product and does not need to be removed by sodium sulfide.
Solvent recycling and reuse have high recycling rates and good economic benefits.
Disadvantages:
Wastewater may be generated during the production process, causing certain pressure on the environment. However, by optimizing the process, such as using desulfurizers, the generation of wastewater can be effectively reduced.
Reaction of Dicyclohexylurea with Trichloromethyl Carbonate
1. Reaction conditions
Dicyclohexylurea reacts with trichloromethyl carbonate under the action of a catalyst to produce DCC. Catalysts are usually anhydrous ferric chloride, zinc chloride, etc. loaded on molecular sieves.
2. Reaction mechanism
Dicyclohexylurea reacts with trichloromethyl carbonate under the action of a catalyst to produce DCC.
This reaction completes the dehydration process through carbonyl alcoholization.
3. Advantages and disadvantages
advantage:
High safety factor and high catalytic efficiency.
Low waste, high purity and yield, suitable for industrial production.
Disadvantages:
The byproduct of DCC reaction, dicyclohexylurea, has low solubility in organic solvents, which poses certain challenges to the purification process. Usually, after distilling off the reaction solvent, solvents such as ether are added to help filter out by-products.
These two preparation methods each have their own advantages and disadvantages, and the choice of method depends on specific production needs, equipment conditions, and environmental requirements. The reaction between cyclohexylamine and carbon disulfide is suitable for situations that require high purity and yield, while the reaction between dicyclohexylurea and trichloromethyl carbonate is more suitable for situations that require large-scale industrial production and focus on safety and environmental protection.
DCC refers to N, N '- dicyclohexylcarbodiimide, a commonly used dehydrating agent, widely used in organic synthesis, especially in esterification or amidation reactions with mild conditions and usually high synthesis yields. Its main function is to convert the hydroxyl groups in carboxylic acids into active acyl intermediates, thereby promoting the formation of amides or esters.
Specific reaction examples:
DCC is commonly used in peptide synthesis and in compounds where amines react with carboxylic acids to form amide bonds, with high reaction yields and fast reaction rates. In addition, DCC is the simplest, gentlest reaction condition, and highest yield coupling reagent for the synthesis of acid anhydrides.
When it comes to esterification reactions, Steglich esterification reaction is one of the most commonly used methods. This reaction was first reported by Wolfgang Steglich in 1978, using DCC as a condensing agent and dehydrating agent, DMAP as a catalyst, to promote esterification reaction under mild conditions. The reaction is usually carried out at room temperature, and dichloromethane is commonly used as a solvent, which is suitable for substrates with high steric hindrance or acid sensitivity, especially for the preparation of tert butyl ester. However, the traditional Fischer esterification method (acid catalyzed esterification) may lead to elimination of the reaction when treating tert butanol. In addition, this reaction can also be used for the synthesis of thioesters. The dehydration byproduct DCC in the reaction is converted into dicyclohexylurea (DCU), which often poses challenges in removing the byproduct. For products with low polarity, DCU can be effectively removed by refining and filtering with ether, methyl tertiary ether, or composite solvents.
The reaction of alcohol oxidation to aldehydes and ketones through DCC and DMSO is also known as Pfitzner Moffatt oxidation. Bronsted acid is often added to catalyze the reaction. It has the advantage of relatively mild reaction conditions, but it produces by-products such as urea that are difficult to remove, and is prone to side reactions such as sulfur etherification, which is also a disadvantage of this reaction.
Under the action of DCC, thiourea can be converted to cyanoguanidine under appropriate reaction conditions.
In addition, Dicyclohexylcarbodiimide powder is often used in dehydration reactions to synthesize compounds with certain special functional groups. In the presence of catalytic CuCl, DCC can serve as an effective dehydrating agent for alcohols, esters, enamines, and nitro compounds.
Frequently Asked Questions
What does DCC do in reaction?
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DCC is a dehydrating agent for the preparation of amides, ketones, and nitriles. In these reactions, DCC hydrates to form dicyclohexylurea (DCU), a compound that is nearly insoluble in most organic solvents and insoluble in water.
What is the use of DCC reagent?
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N,N'-dicyclohexylmethanediimine, commonly known as DCC, is a widely recognized reagent extensively used for protein coupling and various amide bond-forming reactions involving primary and secondary amines with carboxylic acids.
What are the benefits of DCC?
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Some new studies have found that DCC can have a positive effect on both preterm and full-term babies. These benefits include an increase in placental transfusion, a 60% increase of RBCs and a 30% increase in neonatal blood volume. Another advantage of DCC is the decreased risk of iron deficiency anemia.
What does DCC mean medically?
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Disorders of the corpus callosum (DCC) are differences in brain development. They happen when the corpus callosum, the part of the brain that connects the two hemispheres, doesn't form completely (agenesis) or develops differently (dysgenesis).
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