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530-62-1 - 1,1'-Carbonyldiimidazole, 97% - CDI - A14688 - Alfa Aesar

A14688 1,1'-Carbonyldiimidazole, 97%

Codice CAS
530-62-1
Sinonimi
CDI

Dimensioni Prezzo ($) Quantità Disponibilità
10g 38,70
50g 124,00
250g 402,00
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1,1'-Carbonyldiimidazole, 97%

MDL
MFCD00005286
EINECS
208-488-9

Proprietà chimiche

Formula
C7H6N4O
Peso formula
162.15
Punto di fusione
116-120°
Sensibilità
Moisture Sensitive
Solubilità
Soluble in dimethylformamide.

Applicazioni

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.

Note

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

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H302-H314-H318

Harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage.

Dichiarazioni precauzionali: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

Do not breathe dusts or mists. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Merck
14,1819
Beilstein
6826
Classe di rischio
8
Gruppo di imballaggio
II
Codice tariffe armonizzato
2933.29
TSCA
Yes

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