Products
Dicyclohexylcarbodiimide
Synonyms:DCCD;Dicyclohexylcarbodiimide
Chemical Property of Dicyclohexylcarbodiimide
● Appearance/Colour:colorless solid
● Vapor Pressure:1.044-1.15Pa at 20-25℃
● Melting Point:34-35 °C(lit.)
● Refractive Index:n20/D 1.48
● Boiling Point:277 °C at 760 mmHg
● Flash Point:113.1 °C
● PSA：24.72000
● Density:1.06 g/cm3
● LogP:3.82570
● Storage Temp.:Store at RT.
● Sensitive.:Moisture Sensitive
● Solubility.:methylene chloride: 0.1 g/mL, clear, colorless
● Water Solubility.:Reaction
● XLogP3:4.7
● Hydrogen Bond Donor Count:0
● Hydrogen Bond Acceptor Count:2
● Rotatable Bond Count:2
● Exact Mass:206.178298710
● Heavy Atom Count:15
● Complexity:201
● Transport DOT Label:Poison
Safty Information
● Pictogram(s):
T, 
Xn
● Hazard Codes:T,Xn,T+
● Statements:23/24/25-34-40-43-41-36/38-21-24-22-62-37/38-10-61-26-38-20/22
● Safety Statements:26-36/37/39-45-41-24-37/39-24/25-36-16-53-28
Useful
Chemical Classes:Nitrogen Compounds -> Other Nitrogen Compounds
Canonical SMILES:C1CCC(CC1)N=C=NC2CCCCC2
Description:Dicydohexyl carbodiimide is used in peptide chemistry as a coupling reagent. It is both an irritant and a sensitizer, and caused contact dermatitis in pharmacists and chemists.
Uses:In the synthesis of peptides. This product is mainly used in amikacin, glutathione dehydrants, as well as in synthesis of acid anhydride, aldehyde, ketone, isocyanate; when it is used as dehydrating condensing agent, it reacts to dicyclohexylurea through short-time reaction under normal temperature. This product can also be used in synthesis of peptide and nucleic acid. It is easy to use this product to react with compound of free carboxy and amino-group into peptide. This product is widely used in medical, health, make-up and biological products, and other synthetic fields. N,N'-Dicyclohexylcarbodiimide is a carbodiimide used to couple amino acids during peptide synthesis. N,N'-Dicyclohexylcarbodiimide is used as a dehydrating agent for the preparation of amides, ketones , nitriles as well as in the inversion and esterification of secondary alcohols. dicyclohexylcarbodiimide is used as a dehydrating agent at room temperature after a short reaction time, after the reaction product is dicyclohexylurea. the product is very small solubility in an organic solvent, so that easy separation of the reaction product.
Detailed Introduction
Dicyclohexylcarbodiimide (DCC) is a commonly used reagent in organic synthesis. It is a white solid that is insoluble in water and soluble in organic solvents such as ethyl acetate and dichloromethane.
DCC is primarily used as a coupling agent in peptide synthesis and other reactions involving the formation of amide bonds. It promotes the condensation of carboxylic acids with amines, leading to the formation of amides. It accomplishes this by activating the carboxylic acid group and facilitating the nucleophilic attack of the amine on the activated carbonyl carbon.
In addition to peptide synthesis, DCC is also used in various other organic reactions, such as esterification and amidation reactions. It can be employed to form esters from carboxylic acids and alcohols, and to convert carboxylic acid derivatives (such as acid chlorides, acid anhydrides, and activated esters) into amides.
DCC is known for its high efficiency in promoting amide bond formation and for its compatibility with a wide range of functional groups. However, it is also considered to be relatively moisture-sensitive and can easily decompose upon exposure to water or high humidity. Therefore, it is typically handled and stored under anhydrous conditions.
It is important to take necessary precautions when working with DCC, as it can be irritating to the skin, eyes, and respiratory system. Proper ventilation and personal protective equipment should be used during its handling.
Application
Dicyclohexylcarbodiimide (DCC) finds various applications in organic synthesis, particularly in the field of peptide chemistry. Here are a few notable applications of DCC:
Peptide synthesis: DCC is commonly used as a coupling agent in peptide synthesis to join amino acids together and form amide bonds. It promotes the condensation reaction between the carboxyl group of one amino acid and the amino group of another, leading to the formation of peptide bonds.
Esterification reactions: DCC can be used to convert carboxylic acids into esters by reacting them with alcohols. In the presence of DCC, the carboxylic acid is activated, allowing nucleophilic attack by the alcohol to form the ester. This reaction is useful in the synthesis of esters for various applications.
Amidation reactions: DCC can facilitate the amidation of carboxylic acids, acid chlorides, acid anhydrides, and activated esters. It allows the reaction between a carboxylic acid derivative and an amine to form an amide bond. This application finds utility in the synthesis of amides, which are important in various biological and chemical systems.
Ugi reaction: DCC can be utilized in the Ugi reaction, a multicomponent reaction that involves the condensation of an amine, an isocyanide, a carbonyl compound, and an acid. DCC helps in activating the carboxyl group of the acid, allowing it to react with the amine and form an amide bond.
Drug synthesis: DCC is often employed in the pharmaceutical industry for the synthesis of drug candidates and active pharmaceutical ingredients (APIs). Its use in peptide synthesis, amidations, and other important transformations make it an essential reagent in drug discovery and development processes.
It's worth noting that DCC has several other applications in organic synthesis, including the formation of ureas, carbamates, and hydrazides. Its versatility and compatibility with various functional groups make it a valuable tool in the toolbox of synthetic chemists.
