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CDI

(Carbonyldiimidazole)


Other Names:

1,1'-carbonyldiimidazole

N,N'-carbonyldiimidazole





General Information:


Structure:



CAS Number: 530-62-1

Molecular Weight: 162.15 g/mol

Appearance: White cystalline solid

Melting Point: 116-118 C


Carbonyl diimidazole (CDI) is a useful alternative to highly toxic phosgene. CDI is similar to phosgene in its synthetic utility but is easier to handle since it exists as a solid. CDI is moisture sensitive and reacts readily with H2O to evolve CO2. CDI can be used for the activation of carboxylic acids. These activated carboxylic acids can be reacted with nucleophiles to make product that such as amides, esters, ureas, and carbamates. CDI reactions often don’t require a base because the liberated imidazole anion acts a base.




Common Uses:


Reagent for amide formation





Reagent for urea formation





Safety:


Carbonyldiimidazole (CDI) is moisture sensitive and reacts readily with H2O to give off CO2.




References:


1) WO2015144799, page 287

2) WO2015089337, page 98

3) Wikipedia: Carbonyldiimidazole (link)

4) www.sigmaaldrich.com: CDI (link)

5) Pearson, A. J.; Roush, W. R.; Handbook of Reagents for Organic Synthesis, Activating Agents and Protecting Groups

6) Smith, M. B.; March's Advanced Organic Chemistry, 7th Edition




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