8.02954

N,N′-Dicyclohexylcarbodiimide

for peptide synthesis

• Sinônimo(s): N,N′-Dicyclohexylcarbodiimide, DCC
• Fórmula linear: C(NC₆H₁₁)₂
• Número CAS: 538-75-0
• Peso molecular: 206.33
• Número MDL: MFCD00011659
• Código UNSPSC: 12352111
• Número do índice EC: 208-704-1
• NACRES: NA.22

Propriedades

• Nome do produto: N,N′-Dicyclohexylcarbodiimide, for synthesis
• Nível de qualidade: 200
• Formulário: solid
• potência: 1110 mg/kg LD₅₀, oral (Rat); 71 mg/kg LD₅₀, skin (Rat)
• adequação da reação: reaction type: Coupling Reactions
• p.e.: 148-152 °C/15 hPa
• pf: 35-36 °C
• temperatura de transição: flash point 113 °C
• densidade: 0.95 g/cm³ at 40 °C
• densidade volumétrica: 920 kg/m³
• aplicação(ões): peptide synthesis
• temperatura de armazenamento: 2-30°C
• cadeia de caracteres 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
• chave InChI: QOSSAOTZNIDXMA-UHFFFAOYSA-N

Descrição

Descrição geral

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.

Aplicação

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]

Informações de segurança

• Pictogramas: GHS05,GHS06
• Palavra indicadora: Danger
• Frases de perigo: H302 - H311 - H317 - H318
• Declarações de precaução: P261 - P264 - P280 - P301 + P312 - P302 + P352 + P312 - P305 + P351 + P338
• Classificações de perigo: Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Sens. 1
• Código de classe de armazenamento: 6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): 235.4 °F - closed cup
• Ponto de fulgor (°C): 113 °C - closed cup