1,1'-Carbonyldiimidazole

• Catalog No.: A14688
• CAS Number: 530-62-1
• M. F.: C7H6N4O
• M. W.: 162.14874
• Purity: 97%

SYNONYMS

• Title: 1,1'-羰基二咪唑
• IUPAC name: 1-(1H-imidazole-1-carbonyl)-1H-imidazole
• IUPAC Traditional name: carbonyldiimidazole
• Synonyms: CDI

DATABASE IDS

• EC Number: 208-488-9
• CAS Number: 530-62-1
• Merck Index: 141819
• MDL Number: MFCD00005286
• Beilstein Number: 6826

PROPERTIES

• Purity: 97%
• Melting Point: 116-120°C
• GHS Hazard statements: H301-H314-H318
• European Hazard Symbols: X
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 22-34
• Safety Statements: 26-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN3263
• Packing Group: II

REFERENCES

• Reagent for peptide coupling via the acylimidazolide: Liebigs Ann. Chem., 609, 75 (1957); J. Am. Chem. Soc., 80, 4423 (1958); 82, 4596 (1960): J. Org. Chem., 27, 2094 (1962). For peptide reagents, see Appendix 6.
• One-pot esterification of a carboxylic acid with t-BuOH occurs in the presence of DBU: Synthesis, 833 (1982). The reactivity of acyl imidazolides can be increased by N-alkylation: Chem. Pharm. Bull., 32, 5044 (1984).
• Acylimidazolides can also be reduced to aldehydes by DIBAL-H. This reaction has been applied to N-protected amino acids: J. Chem. Soc., Chem. Commun., 79 (1979).
• Dehydrates aldoximes, including chiral oximes, to nitriles in high yield: J. Chem. Soc., Chem. Commun., 628 (1973); Synth. Commun., 12, 25 (1982). Ketoximes can be converted to amides by the spontaneous Beckmann rearrangement of imidazolium salts: Chem. Pharm. Bull., 32, 2560 (1984):
  
• ?-Hydroxy amino acids are dehydrated to dehydroamino acids: Synthesis, 968 (1982).
• ɑ?-Dihydroxyketones are converted toɑ-diketones: Synth. Commun., 23, 2219 (1993).