What is N,N'-Diisopropylcarbodiimide?

Identification

Product Name:    N,N'-Diisopropylcarbodiimide    

Synonyms:    Carbodiimide, diisopropyl-;diisopropyl-carbodiimid;Diisopropylcarbodiimide;N,N'-Diisopropylcarbodiimide≥ 99% (Assay);N,N'-Diisopropylcarbodiimide for synthesis;N,N'-Methanetetraylbis(1-methylethylamine);n,n'-methanetetraylbis(2-propanamine);N,N'-DIISOPROPYLCARBODIIMIDE

CAS:    693-13-0

MF:    C7H14N2

MW:    126.2

EINECS:    211-743-7

Structure:   

Properties

Melting point     210-2120C (dec)    

Boiling point     145-148 °C(lit.)   

Density     0.815 g/mL at 20 °C(lit.)   

Refractive index     n20/D 1.433(lit.)   

Fp     93 °F   

Storage temp.     2-8°C   

Solubility     Slightly soluble in Chloroform, Methanol; Soluble in Methylene Chloride, Acetonitrile, Dioxane, Simethylformamide, Tetrahydrofuran

Form     Liquid    

Color     Clear colorless to yellow    

Sensitive     Moisture Sensitive

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. 

As a reagent

N,N'-Diisopropylcarbodiimide(DIC) is an abbreviated form of N,N′-diisopropylcarbodiimide. It plays a role in the cyclization of N-(β-hydroxy)amides to form 2-oxazolines. Coupling reagent for peptide syntheses. DIC (N,N′-Diisopropylcarbodiimide) has been used in combination with 1-hydroxy-7-azabenzotriazole (HOAt) for the coupling of amino acid with N-allylglycine to form N-allylpeptide. Alternative to dicyclohexylcarbodiimide in peptide synthesis.

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). 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.

Being a liquid, DIC is easier to handle than the solid DCC and forms a DCM-soluble urea by-product, while DCC generates a urea by-product insoluble in most organic solvents. Since the presence of insoluble urea is reportedly problematic in solid-phase peptide synthesis, for this application DIC is more suitable than DCC. A possible side-reaction with DIC and carbodiimides in general is the formation of an N-acylurea, which can be limited by conducting the reaction in DCM or chloroform at low temperatures, and by adding the amine at last.