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

A14688 1,1'-Carbonyldiimidazole, 97%

Número CAS
530-62-1
Nombre Alternativo
CDI

Tamaño Precio ($) Cantidad Disponibilidad
10g 38,52
50g 124,31
250g 369,78
Añadir al carrito Añadir al presupuesto al por mayor Ver artículo

1,1'-Carbonyldiimidazole, 97%

MDL
MFCD00005286
EINECS
208-488-9

Propiedades químicas

Fórmula
C7H6N4O
Peso molecular
162.15
Punto de fusión
116-120°
Sensibilidad
Moisture Sensitive
Solubilidad
Soluble in dimethylformamide.

Aplicaciones

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.

Notas

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

Referencias documentales

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.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H314-H318-H302

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

Indicaciones de precaución: P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P301+P312-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. 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. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Merck
14,1819
Beilstein
6826
Clase de peligro
8
Grupo de embalaje
II
Código de tarifa arancelaria unificado
2933.29
TSCA
Yes

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