1-(1H-imidazole-1-carbonyl)-1H-imidazole

• ChemBase ID: 8903
• Molecular Formular: C7H6N4O
• Molecular Mass: 162.14874
• Monoisotopic Mass: 162.05416083
• SMILES: C(=O)(n1ccnc1)n1ccnc1
• Canonical SMILES: O=C(n1cncc1)n1cncc1
• InChI: InChI=1S/C7H6N4O/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H
• InChIKey: PFKFTWBEEFSNDU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(1H-imidazole-1-carbonyl)-1H-imidazole
• IUPAC Traditional name: carbonyldiimidazole; 1-(imidazole-1-carbonyl)imidazole
• Synonyms: 1,1′-Carbonyldiimidazole solution; N,N'-Carbonyldiimidazole; Di-1H-imidazol-1-yl-methanone; 1,1'-Carbonylbisimidazole; Bis(imidazol-1-yl) Ketone; Bis(imidazol-1-yl)methanone; Diimidazol-1-yl Ketone; N,N-Carbonyldiimidazole; N,N'-Carbonylbis(imidazole); NSC 67203; 1,1'-Carbonyldiimidazole, >90%; 1,1'-Carbonyldiimidazole; Di(1H-imidazol-1-yl)methanone; 1,1'-Carbonyldiimidazole; 1,1'-carbonylbis-1h-imidazole; 1,1'-Carbonyldiimidazole; CDI; N,N'-carbonyldiimidazole; Carbonyldiimidazole; 1,1′-Carbonyldiimidazole; Di(1H-imidazol-1-yl)methanone; 1,1'-Carbonyldi(1H-imidazole) 98%; 1,1′-羰基二咪唑 溶液; 1,1'-羰基二咪唑; 1,1′-羰基二咪唑

Database IDs

• CAS Number: 530-62-1
• EC Number: 208-488-9
• MDL Number: MFCD00005286
• Beilstein Number: 6826
• Merck Index: 141819
• PubChem SID: 24853073; 24847221; 160972210
• PubChem CID: 68263
• Chemspider ID: 61561
• Wikipedia Title: Carbonyldiimidazole

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.95516545
• LogD (pH = 7.4): -0.95410097
• Log P: -0.9540874
• Molar Refractivity: 40.777 cm^3
• Polarizability: 15.467636 Å^3
• Polar Surface Area: 52.71 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Reacts with water
• Apperance: White fine powder
• Melting Point: 110-119°C; 115-122 °C; 116-120°C; 117-122 °C(lit.); 117-122°C; 119°C
• Density: 1.303 g/mL at 25 °C
• Refractive Index: n20/D 1.434

Safety Information

• Storage Condition: 0°C; Refrigerator
• Storage Warning: Corrosive/Harmful/Moisture Sensitive/Store under Argon/Keep Cold; Moisture Sensitive; MOISTURE SENSITIVE, KEEP COLD, CORROSIVE, STORED UNDER ARGON
• European Hazard Symbols: Corrosive (C); X; Harmful (Xn)
• UN Number: 1759; 2922; 3263; UN3263
• German water hazard class: 2; 3
• Hazard Class: 8
• Packing Group: 2; 3; II
• Australian Hazchem: 2X
• Risk Statements: 22-34; 36/38-40; R:34
• Safety Statements: 26-36/37; 26-36/37/39-45; S:26-27/28-36/37/39-46-64
• EU Classification: C10
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: true; 是
• GHS Pictograms: GHS05; GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• Main Hazard: Corrosive
• GHS Hazard statements: H301-H314-H318; H302-H314; H314-H351
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2922 8/PG 3; UN 3263 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (T); 97%; 98%; 98+%
• Concentration: 0.4 M in methylene chloride
• Grade: reagent grade
• Binding Capacity: 10-20 μmol/mL coupling capacity (diaminohexane)
• Extent of Labeling: ≥50 μmol per mL
• Quality Level: PREMIUM
• Matrix: cross-linked 4% beaded agarose
• Matrix Active Group: carbonylimidazole
• Matrix Spacer: 1 atom (when ligands are coupled to the carbonyl group by displacement of imidazole)
• Empirical Formula (Hill Notation): C7H6N4O

DETAILS

MP Biomedicals - 02150558

Purified
Reagent for synthesis of peptides, cyclic carbonates and nucleoside triphosphates.

Sigma Aldrich - 115533

Packaging
1 kg in glass bottle
25 kg in fiber drum
5, 10, 25, 100, 500 g in glass bottle
Application
Coupling agent in the synthesis of dipolar polyamides for nonlinear optical applications1 and polypeptides.2 Also used to make β-keto sulfones and sulfoxides,3 lead sequestering agents,4 and β-enamino acid derivatives.5

Sigma Aldrich - 21860

Other Notes
Reactive reagent for the activation of acids as imidazolides: synthesis of esters, amides, ketones etc. Reagent for immobilizing enzymes and affinity ligands1,2; Carbonyl-transfer reagent for the synthesis of various heterocycles, some recent applications3,4
Packaging
5, 25, 100 g in glass bottle

Sigma Aldrich - 705284

Packaging
100 mL in glass bottle

Toronto Research Chemicals - C177005

Used in the synthesis of peptides. Contains up to 10% imidazole.

REFERENCES

• Anderson, G.W. and Paul, R.J., J. Am. Chem. Soc. , 80 : 4423 (1958).
• Hoard, D.E. and Ott, D.G., Ibid. , 87 : 1785 (1965).
• Pierschbacher, M., et al.: Nature, 309, 30 (1984)
• 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).