8.02954

N,N′-Dicyclohexylcarbodiimide

for peptide synthesis

• Synonym(e): DCC
• Lineare Formel: C(NC₆H₁₁)₂
• CAS-Nummer: 538-75-0
• Molekulargewicht: 206.33
• MDL-Nummer: MFCD00011659
• UNSPSC-Code: 12352111
• EG-Index-Nummer: 208-704-1
• NACRES: NA.22

Eigenschaften

• Produktbezeichnung: N,N′-Dicyclohexylcarbodiimide, for synthesis
• Qualitätsniveau: 200
• Form: solid
• Wirksamkeit: 1110 mg/kg LD₅₀, oral (Rat); 71 mg/kg LD₅₀, skin (Rat)
• Eignung der Reaktion: reaction type: Coupling Reactions
• bp: 148-152 °C/15 hPa
• mp (Schmelzpunkt): 35-36 °C
• Übergangstemp.: flash point 113 °C
• Dichte: 0.95 g/cm³ at 40 °C
• Schüttdichte: 920 kg/m³
• Anwendung(en): peptide synthesis
• Lagertemp.: 2-30°C
• SMILES String: 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
• InChIKey: QOSSAOTZNIDXMA-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

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.

Anwendung

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]

Sicherheitshinweise

• Piktogramme: GHS05,GHS06
• Signalwort: Danger
• H-Sätze: H302 - H311 - H317 - H318
• P-Sätze: P261 - P264 - P280 - P301 + P312 - P302 + P352 + P312 - P305 + P351 + P338
• Gefahreneinstufungen: Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Sens. 1
• Lagerklassenschlüssel: 6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
• WGK: WGK 3
• Flammpunkt (°F): 235.4 °F - closed cup
• Flammpunkt (°C): 113 °C - closed cup