1,1'-Carbonyldiimidazole

Base Information

• Chemical Name: 1,1'-Carbonyldiimidazole
• CAS No.: 530-62-1
• Deprecated CAS: 128456-94-0
• Molecular Formula: C7H6N4O
• Molecular Weight: 162.151
• Hs Code.: 29332990
• European Community (EC) Number: 208-488-9
• NSC Number: 67203
• UNII: 63A10X1FSP
• DSSTox Substance ID: DTXSID9038761
• Nikkaji Number: J182.298E
• Wikipedia: Carbonyldiimidazole
• Wikidata: Q418617
• ChEMBL ID: CHEMBL3903881
• Mol file: 530-62-1.mol

Synonyms:1,1'-carbonyldiimidazole;N,N'-carbonyldiimidazole;N,N-carbonyldiimidazole

Chemical Property of 1,1'-Carbonyldiimidazole

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.006-0.012Pa at 20-25℃
• Melting Point: 117-122 °C(lit.)
• Refractive Index: n20/D1.434
• Boiling Point: 394.6 °C at 760 mmHg
• PKA: 2.90±0.10(Predicted)
• Flash Point: 192.5 °C
• PSA: 52.71000
• Density: 1.39 g/cm³
• LogP: 0.59600
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Soluble in dimethylformamide.
• Water Solubility.: Insoluble in water
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 162.05416083
• Heavy Atom Count: 12
• Complexity: 166

Purity/Quality:

99%min ^*data from raw suppliers

1,1''-Carbonyldiimidazole,>90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi,Xn
• Statements: 22-34-36/37/38-40-36/38
• Safety Statements: 26-36/37/39-45-37/39-27-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Imidazoles
• Canonical SMILES: C1=CN(C=N1)C(=O)N2C=CN=C2
• Mechanochemistry and Solvent-Free Reactions: Mechanochemistry involves applying mechanical forces to enable chemical reactions and is gaining renewed interest in organic synthesis. 1,1'-Carbonyldiimidazole (CDI) facilitates solvent-free reactions, providing an efficient, fast, and environmentally friendly method for synthesizing a wide range of organic compounds.
• Formation of 3,4-Disubstituted 1,2,5-Oxadiazoles: 1,1'-Carbonyldiimidazole (CDI) induces the formation of 3,4-disubstituted 1,2,5-oxadiazoles (furazans) from corresponding bisoximes at ambient temperature. This method allows the synthesis of energetic compounds at temperatures below their decomposition points with improved functional group compatibility.
• Eco-Friendly Acylation Agent: 1,1'-Carbonyldiimidazole (CDI) is utilized as an eco-friendly acylation agent for the mechanochemical preparation of carbamates. It enables the synthesis of various carbamates under mild conditions without the need for additional activation typically required in solution synthesis.
• Polyurethane Synthesis: 1,1'-Carbonyldiimidazole (CDI) serves as a platform for generating high molecular weight polyurethanes from diols and diamines, eliminating the need for isocyanates.; Functionalization of diols with CDI produces electrophilic bis carbamate suitable for further step-growth polymerization with amines, leading to the formation of thermoplastic polyurethanes.; The resulting polyurethanes exhibit high thermal stability, tunable glass transition temperatures, and mechanical ductility, making them suitable for various applications.
• Versatile Applications: CDI's versatility extends to diverse applications, including amidation, functionalization reactions, and the synthesis of various organic compounds such as amides, carboxylic acids, esters, and ureas. Its compatibility with a wide range of substrates and its ability to promote efficient reactions under mild conditions make it a valuable reagent in organic synthesis.

Technology Process of 1,1'-Carbonyldiimidazole

There total 19 articles about 1,1'-Carbonyldiimidazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.8%

1-imidazolylcarbonyl chloride (74731-19-4) + 1-(Trimethylsilyl)imidazole (18156-74-6) → 1,1'-carbonyldiimidazole (530-62-1)

Guidance literature:

at 20 - 35 ℃;

Reference yield: 96.0%

1H-imidazole (288-32-4) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 1,1'-carbonyldiimidazole (530-62-1)

Guidance literature:

With bromobenzene; copper(II) oxide; potassium hydroxide; at 110 ℃; for 5h; Reagent/catalyst; Temperature;

DOI:10.1166/jnn.2018.14582

Reference yield: 90.5%

bis(trichloromethyl) carbonate (32315-10-9) + 1-(Trimethylsilyl)imidazole (18156-74-6) → 1,1'-carbonyldiimidazole (530-62-1)

Guidance literature:

In dichloromethane; at 26 ℃; for 0.5h; Temperature; Inert atmosphere;

upstream raw materials:

1H-imidazole

phosgene

1-(Trimethylsilyl)imidazole

1-imidazolylcarbonyl chloride

Downstream raw materials:

1,3-dihydro-2H-benzimidazol-2-one

Z-Gly-(L)-Phe

meso-N,N'-carbonyl-bis-phenylalanine

ethyl (N-tert-butoxycarbonyl-L-phenylalanyl)glycinate

Refernces

• 1、 -. "Preparation method of carbonyl diimidazole". Paragraph 0015; 0017; 0019; 0021; 0023; 0025; 0027-0032. . Retrieved 2019/02/03.
• 2、 Iannone, Francesco,Casiello, Michele,Monopoli, Antonio,Cotugno, Pietro,Sportelli, Maria Chiara,Picca, Rosaria Anna,Cioffi, Nicola,Dell'Anna, Maria M.,Nacci, Angelo. "Ionic liquids/ZnO nanoparticles as recyclable catalyst for polycarbonate depolymerization". . p. 107 - 116. Retrieved 2016/12/09.