| Identification | More | [Name]
Dicyclohexylcarbodiimide | [CAS]
538-75-0 | [Synonyms]
1,3-DICYCLOHEXYLCARBODIIMIDE
Bis(cyclohexyl)carbodiimide
CYCLOHEXANAMINE, N,N'-METHANETETRAYLBIS-
DCC
DCCD
DCCI
DICYCLOHEXYLCARBODIIMIDE
DICYCLOHEXYLCARBOXIMIDE(1,3-)
N,N-DICYCHOHEXYLCARBODIIMIDE
N,N-DICYCLOHEXYL CARBODIIMIDE
N,N'-DICYCLOHEXYLCARBODIIMIDE
N,N'-DICYLOHEXYLCARBODIIMIDE
Carbodicyclohexylimide
Carbodiimide, dicyclohexyl-
Dicyclimide
dicyclohexyl-carbodiimid
n,n’-dicyclohexylcarbodiimide,1msol.inn-methylpyrrolidone,peptidesynthesisgrade
n,n’-methanetetraylbis-cyclohexaamin
n,n’-methanetetraylbis-cyclohexanamin
N,N’-methanetetraylbis-Cyclohexanamine | [EINECS(EC#)]
208-704-1 | [Molecular Formula]
C13H22N2 | [MDL Number]
MFCD00011659 | [Molecular Weight]
206.33 | [MOL File]
538-75-0.mol |
| Chemical Properties | Back Directory | [Appearance]
N,N0
-Dicyclohexylcarbodiimide (DCC) is
a white crystalline solid. Odor is sweet and heavy. | [Melting point ]
34-35 °C(lit.)
| [Boiling point ]
122-124 °C6 mm Hg(lit.)
| [density ]
1.247 g/mL at 25 °C
| [vapor pressure ]
1.044-1.15Pa at 20-25℃ | [refractive index ]
n20/D 1.48
| [Fp ]
190 °F
| [storage temp. ]
Store at RT. | [solubility ]
methylene chloride: 0.1 g/mL, clear, colorless
| [form ]
Waxy Solid or Crystalline Mass | [color ]
White to pale yellow | [Specific Gravity]
1.247 | [Stability:]
Stable, but moisture sensitive. Combustible. Incompatible with strong oxidizing agents. Avoid exposure to air or moisture. | [Water Solubility ]
Reaction | [Sensitive ]
Moisture Sensitive | [Detection Methods]
GC,NMR | [Merck ]
14,3096 | [BRN ]
610662 | [Contact allergens]
Used in peptide chemistry as a coupling reagent. It is
both an irritant and a sensitizer and has caused contact
dermatitis in pharmacists and chemists. | [InChIKey]
QOSSAOTZNIDXMA-UHFFFAOYSA-N | [LogP]
5.567-6.83 at 25℃ | [CAS DataBase Reference]
538-75-0(CAS DataBase Reference) | [NIST Chemistry Reference]
Methanediimine, n,n'-dicyclohexyl-(538-75-0) | [Storage Precautions]
Moisture sensitive | [EPA Substance Registry System]
538-75-0(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless solid | [Uses]
dicyclohexylcarbodiimide is used as a dehydrating agent at room temperature after a short reaction time, after the reaction product is dicyclohexylurea. the product is very small solubility in an organic solvent, so that easy separation of the reaction product. | [Uses]
N,N'-Dicyclohexylcarbodiimide is a carbodiimide used to couple amino acids during peptide synthesis. N,N'-Dicyclohexylcarbodiimide is used as a dehydrating agent for the preparation of amides, ketones
, nitriles as well as in the inversion and esterification of secondary alcohols. | [Uses]
This product is mainly used in amikacin, glutathione dehydrants, as well as in synthesis of acid anhydride, aldehyde, ketone, isocyanate; when it is used as dehydrating condensing agent, it reacts to dicyclohexylurea through short-time reaction under normal temperature.
This product can also be used in synthesis of peptide and nucleic acid. It is easy to use this product to react with compound of free carboxy and amino-group into peptide.
This product is widely used in medical, health, make-up and biological products, and other synthetic fields.
| [Definition]
ChEBI: A carbodiimide compound having a cyclohexyl substituent on both nitrogen atoms. | [Uses]
In the synthesis of peptides. | [General Description]
White crystalline solid with a heavy sweet odor. | [Reactivity Profile]
N,N'-DICYCLOHEXYLCARBODIIMIDE(538-75-0) 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 (NOx). This compound is incompatible with acids and oxidizing agents. N,N'-DICYCLOHEXYLCARBODIIMIDE(538-75-0) reacts with water. | [Air & Water Reactions]
Sensitive to moisture. | [Hazard]
A poison by skin contact. Moderately toxic
by ingestion and inhalation. | [Potential Exposure]
Laboratory reagent | [Fire Hazard]
This chemical is probably combustible. | [First aid]
Move victim to fresh air. Call 911 or emergency
medical service. Give artificial respiration if victim is not
breathing. Do not use mouth-to-mouth method if victimingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way
valve or other proper respiratory medical device.
Administer oxygen if breathing is difficult. Remove and
isolate contaminated clothing and shoes. In case of contact
with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact,
avoid spreading material on unaffected skin. Keep victim
warm and quiet. Effects of exposure (inhalation, ingestion,
or skin contact) to substance may be delayed. Ensure that
medical personnel are aware of the material(s) involved
and take precautions to protect themselves. Medical observation is recommended for 24 to 48 hours after breathing
overexposure, as pulmonary edema may be delayed.
As first aid for pulmonary edema, a doctor or authorized
paramedic may consider administering a drug or other
inhalation therapy | [Shipping]
UN2928 Toxic solids, corrosive, organic, n.o.s.,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials, 8-
Corrosive material, Technical Name Required. UN2811
Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-
Poisonous materials, Technical Name Required | [Incompatibilities]
Dust may for explosive mixture
with air. Reacts with steam and water. N,N0
-
Dicyclohexylcarbodiimide is an amine/imide: contact
with strong oxidizers may cause fire and explosions.
Incompatible with acids, strong bases, strong reducing
agents (may form flammable gasses); azo and diazo compounds (may form toxic gases); chlorinated hydrocarbons;
nitro compounds. Contact with mixture of acetic acid 1
dinitrogen trioxide may cause explosion. The combustion
of amide compounds generate nitrogen oxides (NOx).
In the presence of moisture, may attack metals and plastics. | [Description]
Dicydohexyl carbodiimide is used in peptide chemistry
as a coupling reagent. It is both an irritant and a
sensitizer, and caused contact dermatitis in pharmacists
and chemists.
| [Waste Disposal]
Whatever cannot be saved for
recovery or recycling should be managed in an appropriate
and approved waste facility. Although not a listed RCRA
hazardous waste, this material may exhibit one or more
characteristics of a hazardous waste and require appropriate
analysis to determine specific disposal requirements.
Processing, use or contamination of this product may
change the waste management options. State and local
disposal regulations may differ from federal disposal
regulations. Dispose of container and unused contents in
accordance with federal, state and local requirements | [Preparation]
A stirred mixture of N,N′-dicyclohexylurea (19.7 g), phosphorus pentoxide (100 g), sand (175 g), and pyridine (700 mL) was refluxed for 2.25 h. Stirring was no longer possible after about 30 min. The mixture was filtered and the residue was extracted with pyridine (100 mL). Pyridine was removed from the combined solutions on a flash evaporator, and the residual oil was extracted with boiling petroleum ether (bp 60–80 C°) (2 × 100 mL), and then with diethyl ether (100 mL). The combined extracts were washed with iced water (3×80 mL), dried over calcium chloride, and filtered. The solvents were removed from the filtrate under reduced pressure to give 17.4 g of an oil, which on distillation yielded 13.7 g (76%) of a clear liquid; bp 143 C° (3.5 mmHg), which solidified in the receiver; mp 34–35 C°.
Another method for producing DCC from dicyclohexylurea is a two-step process using phosphoryl chloride in dichloromethane at 40 C° for 4 h under non-basic conditions followed by removal of acidic components with aq. sodium hydroxide. This method, which gives an 89% yield of DCC, has been presented in a patent application.
 | [Preparation]
Palladium acetate (22 mg, 0.1 mmol), iodine (50 mg, 0.2 mmol), and anhydrous sodium carbonate (320 mg, 3.0 mmol) were placed in a pressure vessel. Cyclohexylamine (0.11 mL, 1.0 mmol) and cyclohexyl isocyanide (0.1 mL, 0.8 mmol) were dissolved in acetonitrile (10 mL) and this solution was added to the reaction vessel, which was then pressurized with oxygen (40 psi) and heated to 100 C° for 3 h. The initially deep-red reaction mixture turned yellow-orange; no Pd black precipitation was observed. There was no obvious reaction rate dependence on oxygen pressure. The mixture was cooled to ambient temperature, depressurized, filtered, and analyzed by GC. DCC was isolated by evaporating the solvent and residual amine, followed by vacuum distillation.
Palladium(II) complexes with a carbodiimide ligand, in which a nitrogen of the linear NbCbN moiety is bonded to the metal center, and bis(carbodiimido)palladium(II) complexes, both derived from isocyanides, have been described. | [Flammability and Explosibility]
Notclassified | [storage]
Color Code—White: Corrosive or Contact Hazard;Store separately in a corrosion-resistant location. KeepDCC in a tightly closed container in a cool, dry, ventilatedarea away from sources of incompatible materials, heat,direct sunlight, moisture, or ignition; best stored under aninert atmosphere at refrigerated temperatures. Containers ofDCC may be hazardous when empty since they retain product residues (dust, solids); observe all warnings and precautions listed for the product. Shelf life when stored underideal conditions: .4 years. | [Purification Methods]
It is sampled as a liquid after melting in warm H2O. It is sensitive to air, and it is a potent skin irritant. It can be distilled in a vacuum and is best stored in a tightly stoppered flask in a freezer. It is very soluble in CH2Cl2 and pyridine where the reaction product with H2O, after condensation, is dicyclohexyl urea which is insoluble and can be filtered off. Alternatively dissolve it in CH2Cl2, add powdered anhydrous MgSO4, shake for 4hours, filter, evaporate and distil at 0.6mm pressure and oil bath temperature of 145o. [Bodansky et al. Biochemical Preparations 10, 122 1963, Schmidt & Seefelder Justus Liebigs Ann Chem 571 83 1951, Schmidt et al. Justus Liebigs Ann Chem 612 11 1958, Beilstein 12 IV 72.] |
| Safety Data | Back Directory | [Hazard Codes ]
T,Xn | [Risk Statements ]
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 ]
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 | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29251900 | [Hazardous Substances Data]
538-75-0(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 1110 mg/kg LD50 dermal Rat 71 mg/kg |
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