8.02954

N,N′-Dicyclohexylcarbodiimide

for peptide synthesis

• Sinónimos: N,N′-Dicyclohexylcarbodiimide, DCC
• Fórmula lineal: C(NC₆H₁₁)₂
• Número de CAS: 538-75-0
• Peso molecular: 206.33
• Número MDL: MFCD00011659
• Código UNSPSC: 12352111
• Número índice de la CE: 208-704-1
• NACRES: NA.22

Propiedades

• Nombre del producto: N,N′-Dicyclohexylcarbodiimide, for synthesis
• Nivel de calidad: 200
• Formulario: solid
• potencia: 1110 mg/kg LD₅₀, oral (Rat); 71 mg/kg LD₅₀, skin (Rat)
• idoneidad de la reacción: reaction type: Coupling Reactions
• bp: 148-152 °C/15 hPa
• mp: 35-36 °C
• temperatura de transición: flash point 113 °C
• densidad: 0.95 g/cm³ at 40 °C
• densidad aparente: 920 kg/m³
• aplicaciones: peptide synthesis
• temp. de almacenamiento: 2-30°C
• cadena 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
• Clave InChI: QOSSAOTZNIDXMA-UHFFFAOYSA-N

Descripción

Descripción general

N,N′-Dicyclohexylcarbodiimide (DCC) is a highly versatile dehydrating reagent with varied applications in organic chemistry. 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.

Aplicación

Recent applications of N,N′-Dicyclohexylcarbodiimide include:

• The synthesis of optically pure N-acyl-N,N′-dicyclohexylureas.
• 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.
• The synthesis of poly (vinyl alcohol-co-vinyl levulinate) copolymers for use in biomedical applications.

Información de seguridad

• Pictogramas: GHS05,GHS06
• Palabra de señalización: Danger
• Frases de peligro: H302 - H311 - H317 - H318
• Consejos de prudencia: P261 - P264 - P280 - P301 + P312 - P302 + P352 + P312 - P305 + P351 + P338
• Clasificaciones de peligro: Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Sens. 1
• Código de clase de almacenamiento: 6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): 235.4 °F - closed cup
• Punto de inflamabilidad (°C): 113 °C - closed cup