538-75-0 Usage
Chemical Description
Dicyclohexylcarbodiimide is a coupling reagent used in organic synthesis.
Chemical Description
Dicyclohexylcarbodiimide is a coupling agent that is used to activate the carboxylic acid group of the amino acid.
Chemical Description
Dicyclohexylcarbodiimide is a coupling reagent used in the synthesis of p-Nitrophenyl benzyloxycarbonyl-D-asparaginate.
Description
Dicyclohexylcarbodiimide, also known as DCC, is a white crystalline solid with a heavy sweet odor. It is a carbodiimide compound that has a cyclohexyl substituent on both nitrogen atoms. DCC is used in peptide chemistry as a coupling reagent and is known to be both an irritant and a sensitizer, causing contact dermatitis in pharmacists and chemists.
Uses
Used in Pharmaceutical Industry:
Dicyclohexylcarbodiimide is used as a dehydrating condensing agent for the synthesis of amikacin and glutathione dehydrants. It is also used in the synthesis of acid anhydride, aldehyde, ketone, and isocyanate. The reaction with DCC leads to the formation of dicyclohexylurea, which has very low solubility in organic solvents, facilitating easy separation of the reaction product.
Used in Peptide Synthesis:
Dicyclohexylcarbodiimide is used as a coupling reagent in peptide chemistry, facilitating the reaction between compounds with free carboxy and amino groups to form peptides. It is particularly useful in the synthesis of peptide and nucleic acid.
Used in Research and Development:
Dicyclohexylcarbodiimide is widely used in medical, health, makeup, and biological products, as well as other synthetic fields. It is also used as a dehydrating agent for the preparation of amides, ketones, nitriles, and in the inversion and esterification of secondary alcohols.
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.
Reactivity Profile
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 (NOx). Dicyclohexylcarbodiimide is incompatible with acids and oxidizing agents. Dicyclohexylcarbodiimide reacts with water.
Fire Hazard
Dicyclohexylcarbodiimide is probably combustible.
Flammability and Explosibility
Notclassified
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.
Potential Exposure
Laboratory reagent
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
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.]
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.
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
Check Digit Verification of cas no
The CAS Registry Mumber 538-75-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 8 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 538-75:
(5*5)+(4*3)+(3*8)+(2*7)+(1*5)=80
80 % 10 = 0
So 538-75-0 is a valid CAS Registry Number.
538-75-0Relevant articles and documents
MIGRATION REVERSIBLE DE PHOSPHORYLE S-P N-P CONTROLEE PAR TRANSFERT DE PROTON, MODELE D'ACTIVATION PAR PHOSPHORYLATION
Blonski, C.,Gasc, M. B.,Klaebe, A.,Perie, J. J.
, p. 2773 - 2776 (1982)
This work describes the reversible C-addition of a sterically hindered-P thiophosphoric ester to a carbodiimide, as a model of activated biotin.The formed intermediate, is found to be in equilibrium with the corresponding N-phosphorylated thiourea.The entire system is controlled by proton transfer and reversible.
Method for preparing N,N'-dicyclohexylcarbodiimide by using co-reactor
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Paragraph 0043-0046, (2021/03/30)
The invention discloses a method for preparing N,N'-dicyclohexylcarbodiimide by using a co-reactor. The method comprises the steps of maintaining an aqueous solution of cyclohexylamine in a strong alkaline environment in the same reactor, adding carbon disulfide into the same reactor, and adding sodium hypochlorite for oxidation to obtain N,N'-dicyclohexylcarbodiimide. According to the method, thetechnological process is simplified through the co-reactor reaction, generation of highly toxic and harmful gas is avoided, the safety risk of production is reduced, and then the purpose of environment-friendly and safe production is achieved.
Microwave-assisted method for synthesizing N,N'-dicyclohexyl carbodiimide
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Paragraph 0032-0051, (2021/04/17)
The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing N,N'-dicyclohexyl carbodiimide through a microwave-assisted method. The method comprises the following steps: dissolving N,N'-dicyclohexyl urea in a solvent under microwave radiation, adding an oxidant and a catalyst loaded on a molecular sieve, and carrying out heat preservation reflux; adding a phase transfer catalyst, adjusting the pH value, and carrying out alkaline hydrolysis reaction; filtering, separating liquid, evaporating out the solvent, and carrying out reduced pressure distillation to obtain N,N'-dicyclohexyl carbodiimide. The catalyst loaded on the molecular sieve is large in specific surface area and high in catalytic efficiency; a microwave-assisted method is adopted, and a phase transfer catalyst is added, so that the problems of difficult two-phase reaction and incomplete reaction in the traditional process are solved, the reaction conversion rate is greatly improved, the reaction time is shortened, and the product has the characteristics of high purity and yield.
Preparation method of dicyclohexylcarbodiimide
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Paragraph 0018-0023, (2020/04/02)
The invention relates to a method for preparing dicyclohexylcarbodiimide by using recycled dicyclohexylurea, and the method comprises the following steps: adding the recycled dicyclohexylurea into a mixed system composed of water and an organic solvent, stirring, washing, filtering, and drying; uniformly stirring the dried dicyclohexylurea and an organic solvent, adding oxalyl chloride at a certain temperature for reaction, keeping the temperature for 0.5 h after dripping is finished, dripping reaction liquid into an aqueous solution of sodium hydroxide, filtering, standing filtrate for layering to obtain an organic phase, concentrating the organic phase, and performing reduced pressure distillation to obtain the dicyclohexylcarbodiimide. According to the method, DCU generated after DCC isused is regenerated into DCC, cyclic application is achieved, the technological method has the advantages of being safe, reliable and high in recovery rate, and industrial production can be achieved.