8.02954

N,N′-Dicyclohexylcarbodiimide

for peptide synthesis

• Synonyme(s) : N,N′-Dicyclohexylcarbodiimide, DCC
• Formule linéaire : C(NC₆H₁₁)₂
• Numéro CAS: 538-75-0
• Poids moléculaire : 206.33
• Numéro MDL: MFCD00011659
• Code UNSPSC : 12352111
• Numéro de classement CE : 208-704-1
• Nomenclature NACRES : NA.22

Propriétés

• Nom du produit: N,N′-Dicyclohexylcarbodiimide, for synthesis
• Niveau de qualité: 200
• Forme: solid
• Puissance: 1110 mg/kg LD₅₀, oral (Rat); 71 mg/kg LD₅₀, skin (Rat)
• Capacité de réaction: reaction type: Coupling Reactions
• pb: 148-152 °C/15 hPa
• Pf: 35-36 °C
• Température de transition: flash point 113 °C
• Densité: 0.95 g/cm³ at 40 °C
• Masse volumique apparente: 920 kg/m³
• Application(s): peptide synthesis
• Température de stockage: 2-30°C
• Chaîne SMILES: N(=C=NC2CCCCC2)C1CCCCC1
• InChI: 1S/C13H22N2/c1-3-7-12(8-4-1)14-11-15-13-9-5-2-6-10-13/h12-13H,1-10H2
• Clé InChI: QOSSAOTZNIDXMA-UHFFFAOYSA-N

Description

Description générale

N,N′-Dicyclohexylcarbodiimide (DCC) is a highly versatile dehydrating reagent with varied applications in organic chemistry.^[1] It is most frequently used as a coupling agent for the synthesis of amides, esters and thioesters from carboxylic acids and amines, alcohol and thiols, respectively. In peptide synthesis applications, DCC is used in conjunction with auxiliary nucleophiles such as Oxyma Pure and HOBt, to minimize side reactions such as racemization, N-acylurea or oxazolone formation. It is used as a dehydration reagent in the Moffatt oxidation of primary alcohols to aldehydes and in the conversion of amides to nitriles. The by-product of the dehydration reaction, dicyclohexylurea, is sparingly soluble in most reaction solvents and can be removed by filtration.

Application

Recent applications of N,N′-Dicyclohexylcarbodiimide include:

• The synthesis of optically pure N-acyl-N,N′-dicyclohexylureas.[2]
• The activation of the carboxylic acid groups in aromatic carboxylic acids to facilitates their reaction with (N-isocyanimino)trifluoroacetamide to form the corresponding 1,3,4-oxadiazole derivatives.[3]
• The synthesis of poly (vinyl alcohol-co-vinyl levulinate) copolymers for use in biomedical applications.[4]

Informations sur la sécurité

• Pictogrammes: GHS05,GHS06
• Mention d'avertissement: Danger
• Mentions de danger: H302 - H311 - H317 - H318
• Conseils de prudence: P261 - P264 - P280 - P301 + P312 - P302 + P352 + P312 - P305 + P351 + P338
• Classification des risques: Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Sens. 1
• Code de la classe de stockage: 6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): 235.4 °F - closed cup
• Point d'éclair (°C): 113 °C - closed cup