CAS 530-62-1 | Coupling Reagents | C7H6N4O | MW 162.15
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What Is CDI (1,1'-Carbonyldiimidazole)? A Direct Answer
CDI (1,1'-Carbonyldiimidazole) (1,1'-Carbonyldiimidazole) is a white to off-white crystalline powder with molecular weight 162.15 g/mol [001]. It serves as CDI's primary advantage over carbodiimides (DCC, EDC) is that it generates only CO2 and imidazole as byproducts, both easily removed, making it the reagent of choice for pharmaceutical API synthesis where residual coupling reagent contamination is a critical quality concern. [002][003].
CDI (1,1'-Carbonyldiimidazole) is commercially available from major chemical suppliers including Sigma-Aldrich (catalog #21860) [002], and is used extensively in activation of carboxylic acids to acyl imidazolides for amide/ester formation and pharmaceutical research.
Key Physical and Chemical Properties
| Property | Value |
|---|---|
| CAS Number | 530-62-1 |
| Molecular Formula | C7H6N4O |
| Molecular Weight | 162.15 g/mol |
| IUPAC Name | di(imidazol-1-yl)methanone |
| InChI Key | PFKFTWBEEZDUMM-UHFFFAOYSA-N |
| Appearance | White to off-white crystalline powder |
| Melting Point | 117-122 °C |
| Solubility | Soluble in THF, DMF, DMSO; reacts with water and alcohols |
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*All property data independently verified against PubChem [001] and Sigma-Aldrich product specifications [002].*
How Is CDI (1,1'-Carbonyldiimidazole) Used in Organic Synthesis?
CDI (1,1'-Carbonyldiimidazole) is CDI's primary advantage over carbodiimides (DCC, EDC) is that it generates only CO2 and imidazole as byproducts, both easily removed, making it the reagent of choice for pharmaceutical API synthesis where residual coupling reagent contamination is a critical quality concern. This makes it the reagent of choice for activation of carboxylic acids to acyl imidazolides for amide/ester formation [003].
The growing demand for CDI (1,1'-Carbonyldiimidazole) in these applications is reflected in market data. The global peptide coupling reagents market (of which CDI is a key player) was valued at approximately USD 2 [003].
In addition to its primary use in activation of carboxylic acids to acyl imidazolides for amide/ester formation, CDI (1,1'-Carbonyldiimidazole) finds widespread application in synthesis of ureas and carbamates from amines [002].
- Conversion of carboxylic acids to aldehydes via reduction
- Preparation of Weinreb amides for ketone synthesis
- Peptide coupling with minimal racemization
What Are the Safety and Handling Requirements for CDI (1,1'-Carbonyldiimidazole)?
Safety is paramount when working with CDI (1,1'-Carbonyldiimidazole). Always consult the Safety Data Sheet (SDS) from your supplier before use. Key handling considerations include:
- Storage: Store in a cool, dry, well-ventilated area. Keep container tightly closed.
- Personal Protection: Wear appropriate PPE including safety glasses, gloves, and lab coat.
- Engineering Controls: Use in a fume hood with adequate ventilation.
- Incompatibilities: Consult the specific SDS for your grade and supplier.
*Note: This is general guidance only. The SDS from your specific supplier is the authoritative safety reference.*
What Does Market Data Tell Us About CDI (1,1'-Carbonyldiimidazole) Supply and Demand?
The global peptide coupling reagents market (of which CDI is a key player) was valued at approximately USD 2.1 billion in 2024, growing at CAGR 4.8% (MarketsandMarkets, 2024). [003].
The global market for chemicals in the coupling reagents category continues to grow, driven by pharmaceutical R&D investment, increasing demand for complex small-molecule drugs, and the expansion of CRO/CDMO services across Asia and North America. Supply chain resilience has become a key consideration for procurement teams, with multi-source strategies increasingly adopted for critical reagents [002].
Frequently Asked Questions About CDI (1,1'-Carbonyldiimidazole)
Q1: What is the shelf life of CDI (1,1'-Carbonyldiimidazole)?
When stored properly under the conditions recommended by the manufacturer, CDI (1,1'-Carbonyldiimidazole) typically maintains its specified purity for 2-3 years from the date of manufacture. Always refer to the Certificate of Analysis (COA) for batch-specific retest dates [002].
Q2: How should I determine the correct grade of CDI (1,1'-Carbonyldiimidazole) for my application?
The appropriate grade depends on your specific application: anhydrous grades for moisture-sensitive reactions; reagent grade (>=98%) for general synthesis; and higher purity grades (>=99%) for analytical or pharmaceutical applications where trace impurities matter [002].
Q3: Can CDI (1,1'-Carbonyldiimidazole) be used as a replacement for similar reagents in established protocols?
While CDI (1,1'-Carbonyldiimidazole) shares functional similarities with related compounds in its class, reaction conditions (solvent, temperature, stoichiometry) often require optimization. Start with literature protocols specific to CDI (1,1'-Carbonyldiimidazole) and adjust as needed [002].
Q4: What are the common impurities found in CDI (1,1'-Carbonyldiimidazole), and how can they affect reactions?
Common impurities vary by manufacturing route. Typical concerns include related structural analogs, residual solvents, or degradation products. Key impurities should be listed on the COA. For catalytic applications where ppm-level impurities matter, consider additional purification if needed [002].
Q5: How does CDI (1,1'-Carbonyldiimidazole) compare to alternative reagents in terms of cost-effectiveness for large-scale production?
CDI (1,1'-Carbonyldiimidazole) often provides a favorable balance of reactivity, selectivity, and commercial availability. For large-scale applications, bulk pricing from major suppliers reduces the cost significantly compared to research-scale quantities. Contact suppliers directly for bulk quotation [002][003].
Q6: What are the recommended solvent systems for reactions involving CDI (1,1'-Carbonyldiimidazole)?
The optimal solvent system depends on the specific reaction type. Common solvents include THF, DMF, DCM, toluene, and acetonitrile [002]. Always ensure anhydrous conditions when specified in the protocol, as CDI (1,1'-Carbonyldiimidazole) may be moisture-sensitive.
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References & Sources
https://www.sigmaaldrich.com/catalog/product/sial/21860