Products
N,N’-Diisopropylcarbodiimide
Synonyms:1,3-diisopropylcarbodiimide
Chemical Property of N,N'-Diisopropylcarbodiimide
● Appearance/Colour:Colorless to pale yellow liquid
● Vapor Pressure:34.9hPa at 55.46℃
● Melting Point:210-212 °C (dec)
● Refractive Index:n20/D 1.433(lit.)
● Boiling Point:146.5 °C at 760 mmHg
● Flash Point:33.9 °C
● PSA：24.72000
● Density:0.83 g/cm3
● LogP:1.97710
● Storage Temp.:2-8°C
● Sensitive.:Moisture Sensitive
● Solubility.:Soluble in chloroform, methylene chloride, acetonitrile, dioxane
● XLogP3:2.6
● Hydrogen Bond Donor Count:0
● Hydrogen Bond Acceptor Count:2
● Rotatable Bond Count:2
● Exact Mass:126.115698455
● Heavy Atom Count:9
● Complexity:101
Safty Information
● Pictogram(s):T+,
T,
F
● Hazard Codes:T+,T,F,Xn
● Statements:10-26-36/37/38-41-42/43-37/38
● Safety Statements:26-36/37/39-45-38-28A-16-22
Useful
Chemical Classes:Nitrogen Compounds -> Other Nitrogen Compounds
Canonical SMILES:CC(C)N=C=NC(C)C
Recent EU Clinical Trials:Long-term effects of Aldara? 5% cream and
DescriptionDiisopropylcarbodiimide (DIC) is a clear liquid that can be easily dispensed by volume. It slowly reacts with moisture from the air, so for long term storage the bottle should be flushed with dry air or inert gas and sealed tightly. It is used in peptide chemistry as a coupling reagent. It is very toxic and caused contact dermatitis in a laboratory worker.
Uses: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'-Diisopropylcarbodiimide is used as a reagent in synthetic organic chemistry. It serves as a chemical intermediate and as a stabilizer for Sarin (chemical weapon). It is also used in the synthesis of peptide and nucleic acid. Further, it is used as an antineoplastic and involved in the treatment of malignant melanoma and sarcomas. In addition to this, it is used in the synthesis of acid anhydride, aldehyde, ketone and isocyanate.
Detailed Introduction
N,N'-Diisopropylcarbodiimide, commonly abbreviated as DIC, is a chemical compound with the molecular formula C7H14N2. It is a colorless liquid that is soluble in common organic solvents like ethers and alcohols. DIC is widely used as an organic synthesis reagent and plays a crucial role in various chemical reactions.
DIC is primarily used as a coupling agent in peptide synthesis, which is the process of joining amino acids together to form peptides or proteins. It acts as a condensing reagent, facilitating the coupling of amino acids by activating carboxyl groups, typically through formation of an unstable intermediate called an active ester. This intermediate reacts with amino groups before undergoing rearrangement and elimination to produce the peptide bond.
DIC is also employed in other reactions beyond peptide synthesis, such as esterifications, amidations, and urethane synthesis. It acts as a dehydrating agent in these reactions, facilitating the removal of water molecules, thereby driving the desired reactions forward.
Due to its reactivity and strong odour, DIC should be handled with caution. It is typically used in a well-ventilated fume hood and protective gloves should be worn to prevent skin contact. Additionally, as with any chemical, it is important to follow proper safety procedures and consult the material safety data sheet (MSDS) for detailed information.
In summary, N,N'-Diisopropylcarbodiimide is a versatile reagent used in organic synthesis for various reactions, including peptide synthesis, esterifications, amidations, and urethane synthesis. Its role as a coupling agent and dehydrating agent makes it a valuable tool in the field of organic chemistry.
Application
N,N'-Diisopropylcarbodiimide (DIC) has several important applications in organic synthesis and pharmaceutical research. Here are some specific uses of DIC:
Peptide synthesis: DIC is commonly used as a coupling agent in solid-phase peptide synthesis to form peptide bonds between amino acids. It activates carboxyl groups of protected amino acids, allowing them to react with amino groups, resulting in the formation of peptide bonds.
Amidation and esterification reactions: DIC is employed as a dehydrating agent to promote the condensation of carboxylic acids with amines or alcohols in amidation and esterification reactions, respectively. It facilitates the formation of amides and esters by removing water from the reaction mixture.
Urethane synthesis: DIC can be used as a coupling agent in the synthesis of urethane compounds. It enables the reaction between isocyanates and alcohols to form urethanes.
Carbodiimide-mediated coupling reactions: DIC is often used as a coupling reagent in various organic reactions, such as the synthesis of amides, peptides, and other biologically active compounds. It promotes the coupling of carboxylic acids, acid chlorides, or acyl azides with amines, hydroxylamines, and other nucleophiles.
Oxidative transformations: DIC can be utilized in oxidative reactions, such as the oxidative cleavage of olefins and the oxidation of sulfides to sulfoxides or sulfones.
It is important to note that DIC is air- and moisture-sensitive, so it should be handled in a well-ventilated area or under an inert atmosphere. Additionally, safety precautions, such as gloves and goggles, should be taken when working with DIC due to its hazardous nature.
