1,1'-Carbonyldiimidazole, 97%, Thermo Scientific Chemicals

Name: 1,1'-Carbonyldiimidazole, 97%, Thermo Scientific Chemicals
SKU: ALFA14688.18

CAS: 530-62-1 | C7H6N4O | 162.15 g/mol

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10 g

Catalog number ALFA14688.18

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Chemical Identifiers

CAS3483-12-3

IUPAC Name(2R,3R)-1,4-disulfanylbutane-2,3-diol

Molecular FormulaC4H10O2S2

InChI KeyVHJLVAABSRFDPM-IMJSIDKUSA-N

SMILESO[C@@H](CS)[C@@H](O)CS

Specifications

Specification Sheet

Appearance (Color)White

Melting point38°C to 43°C

Infrared spectrumConforms

Appearance (Form)Powder or beads

Titration Iodimetric97.5 to 102.5 %

Peptide coupling reagent1,1'-Carbonyldiimidazole acts as a coupling reagent and utilized for coupling of amino acids in order to prepare peptide in organic synthesis. It is also used in the preparation of beta-keto sulfones, sulfoxides and beta-enamino acid derivatives. It is used to convert alcohols and amines into carbamates, esters, and ureas. It is involved in the preparation of formylized imidazole by reaction with formic acid. Further, it is used in the synthesis of dipolar polyamides compounds. In addition to this, it is considered as an equivalent of phosgene and used to prepare asymmetric bis alkyl carbonate.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Peptide coupling reagent1,1′-Carbonyldiimidazole acts as a coupling reagent and utilized for coupling of amino acids in order to prepare peptide in organic synthesis. It is also used in the preparation of beta-keto sulfones, sulfoxides and beta-enamino acid derivatives. It is used to convert alcohols and amines into carbamates, esters, and ureas. It is involved in the preparation of formylized imidazole by reaction with formic acid. Further, it is used in the synthesis of dipolar polyamides compounds. In addition to this, it is considered as an equivalent of phosgene and used to prepare asymmetric bis alkyl carbonate.

Solubility
Soluble in dimethylformamide.

Notes
Store in a cool place. Incompatible with water, strong acids, strong oxidizing agents, strong bases and amines.

RUO – Research Use Only

General 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):
ß-Hydroxy amino acids are dehydrated to dehydroamino acids: Synthesis, 968 (1982).
ɑß-Dihydroxyketones are converted toɑ-diketones: Synth. Commun., 23, 2219 (1993).
Lanzillotto, M.; Konnert, L.; Lamaty, F.; Martinez, J.; Colacino, E. Mechanochemical 1,1'-Carbonyldiimidazole-Mediated Synthesis of Carbamates. ACS Sustainable Chem. Eng. 2015, 3 (11), 2882-2889.
Rodrigues, M. T.; Santos, M. S.; Santos, H.; Coelho, F. 1, 1'-Carbonyldiimidazole mediates the synthesis of N-substituted imidazole derivatives from Morita-Baylis-Hillman adducts. Tetrahedron Lett. 2014, 55 (1), 180-183.
Lafrance, D.; Bowles, P.; Leeman, K.; Rafka, R. Mild Decarboxylative Activation of Malonic Acid Derivatives by 1, 1'-Carbonyldiimidazole. Org. Lett. 2011, 13 (9), 2322-2325.