Dicyclohexylcarbodiimide

Molecule structure of Dicyclohexylcarbodiimide (CAS NO.538-75-0):

IUPAC Name: N,N'-Dicyclohexylmethanediimine 
Molecular Weight: 206.32718 g/mol
Molecular Formula: C₁₃H₂₂N₂ 
Index of Refraction: 1.567
Molar Refractivity: 63.46 cm³
Molar Volume: 194.2 cm³
Surface Tension: 39.2 dyne/cm
Density: 1.06 g/cm³ 
Melting Point: 34-35 °C(lit.)
Boiling Point: 277 °C at 760 mmHg 
Flash Point: 113.1 °C
Index of Refraction: 1.567
Molar Refractivity: 63.46 cm³
Molar Volume: 194.2 cm³
Surface Tension: 39.2 dyne/cm 
Enthalpy of Vaporization: 49.48 kJ/mol
Vapour Pressure: 0.00783 mmHg at 25 °C 
Storage Temp.: store at RT. 
Methylene chloride Solubility: 0.1 g/mL, clear, colorless
Water Solubility: reaction
Sensitive Moisture: sensitive
XLogP3-AA: 4.7
H-Bond Acceptor: 2
Rotatable Bond Count: 2
Exact Mass: 206.178299
MonoIsotopic Mass: 206.178299
Topological Polar Surface Area: 24.7
Heavy Atom Count: 15
Canonical SMILES: C1CCC(CC1)N=C=NC2CCCCC2
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
EINECS: 208-704-1
Product Categories: Pharmaceutical Intermediates; Amino Acid Derivatives; Starting Raw Materials & Intermediates; Miscellaneous; Organics; Coupling Reagent; Peptide Coupling Reagents; Condensing Agents (DNA / RNA Synthesis); Biochemistry; Condensation & Active Esterification; Coupling Reactions (Peptide Synthesis); Nucleosides, Nucleotides & Related Reagents; Peptide Synthesis; Protecting Agents, Phosphorylating Agents & Condensing Agents; Reagents for Oligosaccharide Synthesis; Synthetic Organic Chemistry; Peptide; Protected Amino Acids; Synthetic Reagents; CarbodiimidesSynthetic Reagents; Carbodiimides; Coupling; Peptide Synthesis

The primary use of Dicyclohexylcarbodiimide (CAS NO.538-75-0) is to couple amino acids during artificial peptide synthesis.

 Dicyclohexylcarbodiimide has several synthesis methods. Pri-Bara et al. use palladium acetate, iodine, and oxygen to couple cyclohexyl amine and cyclohexyl isocyanide. 
C₆H₁₁NC + C₆H₁₁NH₂ + O₂ → (C₆H₁₁N)₂C + H₂O
Tang et al. condense two isocyanates using the catalyst OP(MeNCH₂CH₂)₃N in yields of 92%:

 Dicyclohexylcarbodiimide has also been made from dicyclohexylurea using a phase transfer catalyst by Jaszay et al. The disubstituted urea, arenesulfonyl chloride, and potassium carbonate react in toluene in the presence of benzyl trimethylammonium chloride to give Dicyclohexylcarbodiimide in 50% yield.

Hazard Codes: T,Xn
Risk Statements: 23/24/25-34-40-43-41-36/38-21-24-22-62-37/38-10-61
R23/24/25:  Toxic by inhalation, in contact with skin and if swallowed 
R34:  Causes burns 
R40:  Limited evidence of a carcinogenic effect 
R43:  May cause sensitization by skin contact 
R41:  Risk of serious damage to eyes 
R36/38:  Irritating to eyes and skin 
R21:  Harmful in contact with skin 
R24:  Toxic in contact with skin 
R22:  Harmful if swallowed 
R62:  Possible risk of impaired fertility 
R37/38:  Irritating to respiratory system and skin 
R10:  Flammable 
R61:  May cause harm to the unborn child 
Safety Statements: 26-36/37/39-45-41-24-37/39-24/25-36-16-53
S26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37/39:  Wear suitable protective clothing, gloves and eye/face protection 
S45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
S41:  In case of fire and/or explosion do not breathe fumes
S24:  Avoid contact with skin 
S37/39:  Wear suitable gloves and eye/face protection 
S24/25:  Avoid contact with skin and eyes 
S36:  Wear suitable protective clothing
S16:  Keep away from sources of ignition - No smoking 
S53:  Avoid exposure - obtain special instruction before use 
RIDADR: UN 2922 8/PG 2
WGK Germany: 3
RTECS: FF2160000
F: 3-8-10-21: Hygroscopic. Photosensitive. Keep under argon. Sensitive to humidity.
HazardClass: 6.1
PackingGroup: II

 Dicyclohexylcarbodiimide (CAS NO.538-75-0) is also named as 1,3-Dicyclohexylcarbodiimide ; Bis(cyclohexyl)carbodiimide ; Carbodicyclohexylimide ; DCC ; DCCD ; DCCI ; N,N'-Dicyclohexylcarbodiimide ; N,N'-Methanetetraylbiscyclohexaamine ; NSC 30022 . Dicyclohexylcarbodiimide (CAS NO.538-75-0) is colorless solid with a heavy sweet odor. Dicyclohexylcarbodiimide is an imide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P₂O₅ or SOCl₂ generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NO_x). Dicyclohexylcarbodiimide is incompatible with acids and oxidizing agents. It is probably combustible.