N-(N-cyclohexylcarboximidoyl)cyclohexanamine

• ChemBase ID: 102408
• Molecular Formular: C13H22N2
• Molecular Mass: 206.32718
• Monoisotopic Mass: 206.17829871
• SMILES: C1CCC(CC1)N=C=NC1CCCCC1
• Canonical SMILES: C1CCC(CC1)N=C=NC1CCCCC1
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(N-cyclohexylcarboximidoyl)cyclohexanamine
• IUPAC Traditional name: dicyclohexylcarbodiimide
• Synonyms: DCC; N,N'-DICYCLOHEXYL CARBODIIMIDE; DCC solution; N,N′-Dicyclohexylcarbodiimide solution; N,N′-Dicyclohexylcarbodiimide; N,N'-Dicyclohexylcarbodiimide; N,N′-Methanetetraylbis[cyclohexanamine]; NSC 30022; NSC 53373; NSC 57182; Dicyclohexylcarbodiimide solution; DCC 溶液; N,N′-二环己基碳二亚胺 溶液; N,N′-二环己基碳二亚胺; N,N'-二环己基碳二亚胺; 二环己基碳二亚胺 溶液

Database IDs

• CAS Number: 538-75-0
• EC Number: 208-704-1
• MDL Number: MFCD00011659
• Beilstein Number: 610662
• Merck Index: 143096
• PubChem SID: 24894174; 162089073; 24863614; 22435037; 24862661
• PubChem CID: 10868

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.7913857
• LogD (pH = 7.4): 3.792248
• Log P: 3.7922592
• Molar Refractivity: 62.3204 cm^3
• Polarizability: 24.36774 Å^3
• Polar Surface Area: 24.72 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: methylene chloride: soluble0.1 g/mL at 20 °C, clear, colorless; methylene chloride: soluble0.1 g/mL, clear, colorless
• Melting Point: 33-35 °C; 33-36°C; 34.5-37.0 °C; 34-35 °C(lit.); 34-35°C
• Boiling Point: 122-124 °C/6 mmHg(lit.); 154-156°C @ 11 mm; 122-124°C @ 6 mm; 154-156°C/11mm
• Flash Point: 110°C; 113 °C; 138°C(280°F); 190.4 °F; 203 °F; 235.4 °F; 30 °C; 86 °F; 88 °C; 95 °C
• Density: 0.898 g/mL at 25 °C; 1.247 g/mL at 25 °C
• Refractive Index: n20/D 1.480; n20/D 1.503

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Moisture Sensitive
• RTECS: FF2160000
• European Hazard Symbols: Corrosive (C); Toxic (T); Harmful (Xn)
• UN Number: 2810; 2811; 2922; 2929; UN2811
• German water hazard class: 1; 2; 3
• Hazard Class: 6.1; 8
• Packing Group: 2; III
• Australian Hazchem: 2X
• Risk Statements: 10-20/22-24-38-41-43; 21-41-43; 22-24-40-41-43; 22-24-41-43; R:22-24-34-41-43
• Safety Statements: 24-26-37/39-45; 26-36/37/39; 26-36/37/39-45; S:24-26-45-37/39
• EU Classification: CT1
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H312-H315-H317-H318; H302-H311-H317-H318; H311-H302-H317-H318; H317-H318; H317-H318-H351
• GHS Precautionary statements: P261-P305+P351+P338-P361-P302+P352-P405-P501A; P280-P305 + P351 + P338; P280-P305 + P351 + P338-P312
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2810 6.1/PG 2; UN 2811 6.1/PG 2; UN 2922 8/PG 2; UN 2929 6.1/PG 2

Pharmacology Properties

• Gene Information: human ... EPHX2(2053)mouse ... Ephx2(13850)

Product Information

• Purity: ≥99.0% (GC); 99%
• Concentration: ~1 M in NMP; 1.0 M in methylene chloride; 60 wt. % in xylenes
• Grade: puriss.; purum
• Linear Formula: C6H11N=C=NC6H11
• Empirical Formula (Hill Notation): C13H22N2

DETAILS

MP Biomedicals - 02101556

Peptide condensing agent.

Sigma Aldrich - 633267

Packaging
100, 800 mL in glass bottle
Application
Catalyst for Mitsunobu reaction to synthesize tetramethylpyrazine derivatives1Coupling agent for generation of graphene and graphene oxide sheets supported on silica2Endophytic bacterium L14 biomass inhibitor3Used to produce:
• Multifunctional aqueous nanocrystals stabilized by hyperbranched polyglycerol4
• MnO2 nanosheets attached to Au nanoparticles on carbon nantubes5
• Functionalized single-walled carbon nantotube arrays6

Sigma Aldrich - 379115

Packaging
100, 800 mL in Sure/Seal™

Sigma Aldrich - D80002

Application
Carboxy group activating reagent for peptide synthesis.1
Packaging
1 kg in poly bottle
25, 100, 500 g in poly bottle
5 kg in poly drum

Sigma Aldrich - 36650

Other Notes
Coupling reagent, reagent for dehydrations etc. Modifies bovine heart mitochondrial transhydrogenase;1,2 Inhibition of F1F0-ATPase and other proton-translocating enzymes3

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: