N,N'-Dicyclohexylcarbodiimide

• Catalog No.: A10973
• CAS Number: 538-75-0
• M. F.: C13H22N2
• M. W.: 206.32718
• Purity: 99%

SYNONYMS

• Title: N,N'-二环己基碳二亚胺
• IUPAC name: N-(N-cyclohexylcarboximidoyl)cyclohexanamine
• IUPAC Traditional name: dicyclohexylcarbodiimide
• Synonyms: DCC

DATABASE IDS

• CAS Number: 538-75-0
• EC Number: 208-704-1
• MDL Number: MFCD00011659
• Beilstein Number: 610662
• Merck Index: 143096

PROPERTIES

• Purity: 99%
• Boiling Point: 154-156°C/11mm
• Flash Point: 138°C(280°F)
• Melting Point: 33-36°C
• GHS Hazard statements: H311-H302-H317-H318
• European Hazard Symbols: Toxic (T)
• GHS Precautionary statements: P261-P305+P351+P338-P361-P302+P352-P405-P501A
• Risk Statements: 22-24-41-43
• RTECS: FF2160000
• Safety Statements: 24-26-37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN2811
• Packing Group: III

REFERENCES

• In peptide coupling reactions, various auxiliary reagents have been used to suppress racemization. See, e.g., N-Hydroxysuccinimide, A10312, N-Hydroxyphthalimide, A13862, and endo-N-Hydroxy-5-norbornene-2,3-dicarboximide, A13205. For use of CuCl₂, see: Tetrahedron Lett., 25, 771 (1984); J. Chem. Soc., Chem. Commun., 419 (1988).
• For ester or thioester formation from an acid and an alcohol, the rate is greatly increased by addition of 4-(Dimethylamino)pyridine, A13016: Angew. Chem. Int. Ed., 17, 522 (1978). For t-butyl esters, see: Org. Prep. Proced. Int., 20, 180 (1988); Org. Synth. Coll., 7, 93 (1990). The same combination has been found useful in macrolactonization reactions: J. Org. Chem., 50, 2394 (1985); and in formation of propynoic esters under mild conditions: Tetrahedron Lett., 30, 4575 (1989).
• DCC-coupling is frequently used to prepare active esters, e.g. of 4-Nitrophenol, A14376, or Pentafluorophenol, A15574, for peptide coupling; see Appendix 6.
• DCC has also been used in dehydrations, e.g. carboxylic acids to anhydrides: J. Am. Chem. Soc., 85, 1997 (1963); J. Org. Chem., 54, 1922 (1989); primary amides: J. Org. Chem., 26, 3356 (1961), and aldoximes: Synth. Commun., 3, 101 (1973); 12, 25 (1982) to nitriles; dialkylacetic acids to ketenes (where stable): Synthesis, 568 (1989). The combination with Dimethyl sulfoxide, A13280, is used in the Pfitzner-Moffatt oxidation of alcohols to carbonyl compounds under mild conditions: J. Am. Chem. Soc., 85, 3027 (1963); 87, 5661, 5670 (1965); Org. Synth. Coll., 5, 242 (1973); review: Synthesis, 857 (1990).
• In the presence of H₂SO₄ or AlCl₃, Friedel-Crafts cyclohexylation of arenes has been reported: Tetrahedron Lett., 35, 903 (1994).
• For reviews of advances in the chemistry of carbodiimides, see: Chem. Rev., 67, 107 (1967), 81, 589 (1981); Tetrahedron, 37, 233 (1981).
• Promotes a variety of acylation reactions between carboxylic acids and nucleophiles; the dicyclohexylurea by-product is almost insoluble in most solvents: