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Dicyclohexylcarbodiimide

CAS No.
538-75-0
Chemical Name:
Dicyclohexylcarbodiimide
Synonyms
DCC;DCCI;1,3-DICYCLOHEXYLCARBODIIMIDE;DCCD;N,N-DICYCLOHEXYL CARBODIIMIDE;N,N'-DICYCLOHEXYLCARBODIIMIDE;dicyclohexyl-carbodiimid;N,N'-Dicyclohexylmethanediimine;Bis(cyclohexyl)carbodiimide;DCC/DCCI
CBNumber:
CB9706578
Molecular Formula:
C13H22N2
Molecular Weight:
206.33
MDL Number:
MFCD00011659
MOL File:
538-75-0.mol
MSDS File:
SDS
Last updated:2024-03-27 14:25:11

Dicyclohexylcarbodiimide Properties

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
Flash point 190 °F
storage temp. Store below +30°C.
solubility methylene chloride: 0.1 g/mL, clear, colorless
form Waxy Solid or Crystalline Mass
Specific Gravity 1.247
color White to pale yellow
Sensitive Moisture Sensitive
Merck 14,3096
BRN 610662
Stability Stable, but moisture sensitive. Combustible. Incompatible with strong oxidizing agents. Avoid exposure to air or moisture.
InChIKey QOSSAOTZNIDXMA-UHFFFAOYSA-N
LogP 5.567-6.83 at 25℃
CAS DataBase Reference 538-75-0(CAS DataBase Reference)
EWG's Food Scores 1-3
FDA UNII 0T1427205E
NIST Chemistry Reference Methanediimine, n,n'-dicyclohexyl-(538-75-0)
EPA Substance Registry System Dicyclohexylcarbodiimide (538-75-0)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS05,GHS07,GHS08
Signal word  Danger
Hazard statements  H312-H315-H317-H318-H336-H351
Precautionary statements  P202-P261-P280-P302+P352+P312-P305+P351+P338-P308+P313
Hazard Codes  T,Xn,T+
Risk Statements  23/24/25-34-40-43-41-36/38-21-24-22-62-37/38-10-61-26-38-20/22
Safety Statements  26-36/37/39-45-41-24-37/39-24/25-36-16-53-28
RIDADR  UN 2922 8/PG 2
WGK Germany  3
RTECS  FF2160000
3-8-10-21
TSCA  Yes
HazardClass  6.1
PackingGroup  II
HS Code  29252000
Toxicity LD50 orally in Rabbit: 1110 mg/kg LD50 dermal Rat 71 mg/kg
NFPA 704
1
3 0

Dicyclohexylcarbodiimide price More Price(60)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.02954 N,N′-Dicyclohexylcarbodiimide for synthesis 538-75-0 250g $164 2024-03-01 Buy
Sigma-Aldrich 8.02954 N,N′-Dicyclohexylcarbodiimide for synthesis 538-75-0 1kg $403 2024-03-01 Buy
Sigma-Aldrich 8.02954 N,N′-Dicyclohexylcarbodiimide for synthesis 538-75-0 2.5kg $659 2024-03-01 Buy
Sigma-Aldrich 36650 DCC puriss., ≥99.0% (GC) 538-75-0 100g $91.7 2024-03-01 Buy
Sigma-Aldrich 36650 DCC puriss., ≥99.0% (GC) 538-75-0 2.5kg $352 2024-03-01 Buy
Product number Packaging Price Buy
8.02954 250g $164 Buy
8.02954 1kg $403 Buy
8.02954 2.5kg $659 Buy
36650 100g $91.7 Buy
36650 2.5kg $352 Buy

Dicyclohexylcarbodiimide Chemical Properties,Uses,Production

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.

Chemical Properties

Colorless solid

Chemical Properties

N,N0 -Dicyclohexylcarbodiimide (DCC) is a white crystalline solid. Odor is sweet and heavy.

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

In the synthesis of peptides.

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.

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.
DCC.jpg

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.

Definition

ChEBI: A carbodiimide compound having a cyclohexyl substituent on both nitrogen atoms.

General Description

White crystalline solid with a heavy sweet odor.

Air & Water Reactions

Sensitive to moisture.

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.

Hazard

A poison by skin contact. Moderately toxic by ingestion and inhalation.

Fire Hazard

Dicyclohexylcarbodiimide is probably combustible.

Flammability and Explosibility

Not classified

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

First aid

Eyes: Check the victim for contact lenses andremove. Flush victim’s eyes with water or normal salinesolution for 20-30 min, lifting lower and upper eyelidsoccasionally. Remove contaminated clothing and shoes. Getmedical attention immediately. Do not put any ointments,oils, or medication in the victim’s eyes without specificinstructions from a physician. Immediately transport thevictim after flushing eyes to a hospital even if no symptoms(such as redness or irritation) develop. Skin: Immediatelyflood affected skin with water and wash for at least 15 min.Remove and isolate all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. Ifsymptoms such as redness or irritation develop, immediately call a physician. Transport the victim to a hospital fortreatment. Inhalation: Remove victim to fresh air. If notbreathing, give artificial respiration. If breathing is difficult,give oxygen. Get medical attention immediately. Ingestion:Do not induce vomiting. If the victim is conscious and notconvulsing, give large amount of water to dilute the chemical. Never give anything by mouth to an unconscious person. If symptoms (such as wheezing, coughing, shortness ofbreath, or burning in the mouth, throat, or chest) develop,call a physician. In all cases get medical attention immediately. If the victim is convulsing or unconscious, do notgive anything by mouth, ensure that the victim’s airway isopen and lay the victim on his/her side with the head lowerthan the body.

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.

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

2387-23-7
538-75-0
Synthesis of Dicyclohexylcarbodiimide from N,N'-DICYCLOHEXYLUREA
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Dicyclohexylcarbodiimide pictures 2024-03-28 Dicyclohexylcarbodiimide
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N,N'-Dicyclohexylcarbodiimide for synthesis N,N'-DICYLOHEXYLCARBODIIMIDE N,N-DICYCHOHEXYLCARBODIIMIDE 1,3-DICYCLOHEXYLCARBODIIMIDE, 1.0M SOLUT ION IN DICHLOROMETHANE N,N-DICYCLOHEXYLCARBODIIMIDE SOLUTION, ~1 M IN NMP N,N'-DICYCLOHEXYLCARBODIIMIDE SOL. ~1 M IN DICHLOROMETHANE DCC (N, N'-Dicyclohexylcarbodiimide N,N-Dicyclohexylcarbodiimide99% N,N'DicyclohexylcarbodimideForSynthesis DCC (N,N-dichyclohexylcarbodiimide) N'N-dicyclohexylcarbodiimide(DCC) Dicyclohexylcarbodiimide solution DCC impregnated tablets, ChemDose(R), N,Nμ-Dicyclohexylcarbodiimide impregnated tablets N,Nμ-Dicyclohexylcarbodiimide, ChemDose(R) tablets N,N′-Dicyclohexylcar N,N'-Dicyclohexylcarbodiimide, 1M solution in dichloromethane, AcroSeal N,N-Dicyclohexyl carbodiimine N,Nzzhlxy-Dicyclohexylcarbodiimide (DCC) N,N'-MethanediylidenedicyclohexanaMine NSC 30022 NSC 53373 NSC 57182 DCC/DCCI N,N''-DICYCLOHEXYLCARBODIIMIDE FOR SYNTHE N-N,dicyclohexyliMinecarbontwo DCC puriss., >=99.0% (GC) n,ni-dicyclohexylcarbodiimide N,N'-Methanetetraylbiscyclohexanamine N,N′-Dicyclohexylcarbodiimide, ChemDose? tablets N,N’-methanetetraylbis-Cyclohexanamine NN'Dicyclohexylcarbodie DCC 1.0 M in methylene chloride N,N'-Dicyclohexylcarbodiimide CYCLOHEXANAMINE, N,N'-METHANETETRAYLBIS- DICYCLOHEXYLCARBODIIMIDE DICYCLOHEXYLCARBOXIMIDE(1,3-) N,N'-Dicyclohexylcarbodiimide [for Peptide Synthesis] N,N'-Dicyclohexylcarbodiimide, 0.1M sol.in DCM, peptide synthesis grade N,N'-Dicyclohexylcarbodiimide, 1 M solution in dichloromethane N,N'-Dicyclohexylcarbodiimide, 1M sol. In N-methylpyrrolidone,peptide synth.grade N,N'-Dicyclohexylcarbodiimide,>98% dcc solution n,n'-dicyclohexylcarbodiimide solution DCC Dicyclohexylcarbodiimide DCC N,N''-DICYCLOHEXYLCARBODIMIDE N,N''-DICYCLOHHEXYLCARBODIIMIDE Dicyclohexyl Carbidiimide N,N'-Dicyclohexylcarbodiimide (25% in Pyridine, ca. 1.2mol/L) N,N'-DICYCLOHEXYLCARBODIMIDE pure Carbodicyclohexylimide Carbodiimide, dicyclohexyl- Dicyclimide n,n’-dicyclohexylcarbodiimide,1msol.inn-methylpyrrolidone,peptidesynthesisgrade n,n’-methanetetraylbis-cyclohexaamin n,n’-methanetetraylbis-cyclohexanamin 1,3-Dicyclohexylcarbodiimide solution (1.0 M in methylene chloride) 1,3-Dicyclohexylcarbodiimide≥ 99% (GC) 1,3-Dicyclohexylcarbodiimide solution(50% in THF)≥ 99% (GC)