Substance

ID:717222

1,1'-Carbonyldiimidazole

Names and Identifiers
IUPAC name
1-(1H-imidazole-1-carbonyl)-1H-imidazole
IUPAC Traditional name
carbonyldiimidazole
Synonyms
CDI1,1'-Carbonyldiimidazole1,1'-羰基二咪唑
Registration numbers
CAS Number
Beilstein Number
MDL Number
EC Number
Merck Index
Properties
Safety Information
Risk Statements
22-34
Packing Group
II
GHS Hazard statements
H301-H314-H318
GHS Precautionary statements
P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A
Safety Statements
26-36/37/39-45
Storage Warning
Moisture Sensitive
Hazard Class
8
GHS Pictograms
GHS06
Acute toxicity (oral, dermal, inhalation), categories 1,2,3
GHS05
Corrosive to metals, category 1
Skin corrosion, categories 1A,1B,1C
Serious eye damage, category 1
UN Number
UN3263
European Hazard Symbols
Harmful Harmful (X)
Corrosive Corrosive (C)
TSCA Listed
Product Information
Purity
97%
Physical Property
Melting Point
116-120°C
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• ?-Hydroxy amino acids are dehydrated to dehydroamino acids: Synthesis, 968 (1982).
• 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):
• 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).
• ɑ?-Dihydroxyketones are converted toɑ-diketones: Synth. Commun., 23, 2219 (1993).
• 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.
• 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).