PRODUCT IDENTIFICATION

H.S. CODE

TOXICITY

C1CCC(CC1)N=C=NC2CCCCC2

CLASSIFICATION

EXTRA NOTES

PHYSICAL AND CHEMICAL PROPERTIES

AUTOIGNITION

NFPA RATINGS

REFRACTIVE INDEX

113 C

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking

Google Scholar Search

Drug Information Portal (U.S. National Library of Medicine) - Dicyclohexylcarbodiimide

PubChem Compound Summary - Dicyclohexylcarbodiimide

http://www.ebi.ac.uk/ -  Dicyclohexylcarbodiimide

http://www.ncbi.nlm.nih.gov/ -  Dicyclohexylcarbodiimide

Material Safety Data Sheet

http://www.bgu.ac.il/
Carbodiimide reagents were designed to prevent the formation of the undesired N-acylurea and to facilitate easy separation from the by-products. The insolubility of the by-product occasionally caused problems for the synthesis of polypeptides. Since the ureas from DIC and CIC were relatively soluble in CH2Cl2, these reagents were more suitable for solid-phase peptide synthesis than DCC. The solubilities of N-cyclohexyl-N0-isopropylurea, N,N0-diisopropylurea, and N,N0-dicyclohexylurea were 30, 5.2 and 1.5 g/L in CH2Cl2, respectively. In Fmoc solid-phase peptide synthesis, the DIC/additive method was investigated in various conditions by changing the additive, base,and solvent. Carpino demonstrated that DIC/HOAt was superior to DIC/other additives.43 Further variations of the carbodiimide such as BMC, BEC, and N,N0-dicyclopentylcarbodiimide were reported (Fig. 12).44 Rapoport developed the hydrophilic side-chain-containing carbodiimide, BDDC, in 1994. BDDC in THF, DMF, or toluene gave a reasonable yield for the coupling reaction with a Bocprotected amino acid and the by-product was easily removed by an acid wash.

http://www.peptide-and-dna.com/
The formation of the amide bond together with chirality of the molecules plays a key role in the preparation of a broad range of organic compounds. It begins with the small molecules through the peptides to fully synthetic proteins. Today, the synthesis of peptide or protein based pharmaceutical drug requires up to 100 steps, the name of the game is ˇ°production costˇ± and the modern synthetic technologies play a central role in this battleA. thorough study of the mechanism in each method involving basic producer for logistic and technical support is a necessary term for the optimization of the coupling step of a new peptide drug and further up-scaling towards bulk manufacturing. Today, Cl-HOBt as an additive and HCTU/TCTU are excellent alternatives to the most classic methods for the large scale manufacturing of peptide and proteins.

Local:
Carbodiimides are a group of organic compounds which have the resonance formula  N=C=N. Carbodiimide is formed by dehydration of urea or from thiourea. Carbodiimides are readily reacts with various form of amines and hydroxyl functional groups. Carbodiimides are used as dehydration agents and as activating agent of carboxylic acids to form esters or amides. The disubstituted carboxyl activating agents are used for crosslinking proteins to nucleic acids and formation of immunoconjugates in peptide synthesis. N,N'-dicyclohexylcarbodiimide (DCC) is one of the most common peptide coupling agents. It is a low melting point waxy solid; insoluble in water but highly soluble in common organic solvents like acetonitrile dichloromethane, dimethylformamide, and tetrahydrofuran. DCC is a potent allergen. N,N'-diisopropylcarbodiimide (DIC) is an alternative to DCC, DIC is a liquid and is not an allergen. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) is a water-soluble activating agent for amide bonding with primary amines. It also activates phosphate groups. Typically, it is utilized in the pH range 4.0-6.0 without buffers. In particular, amine and carboxylate buffers should be avoided. Carbodiimides are so active and cause racemization of the amino acid. Active esters are less reactive and less in danger of racemization. 1-Hydroxybenzotriazole (HOBt) and 1-hydroxy-7-aza-benzotriazole (HOAt) are substances that react with the O-acylurea to form active esters. HOAt is a condensation additive in peptide synthesis. It efficiently speeds up coupling process, reduces the loss of chiral integrity, and provides a visual indication (yellow to colorless) of the reaction course. Other active esters exit as non-nucleophilic anionic salts of uronium or phosphonium such as O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate(HBTU), O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU), (Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP). Carbodiimides are a group of organic compounds which have the resonance formula  N=C=N having .Carbodiimides are formed by dehydration of ureas or from thioureas. Carbodiimides are readily reacts with various form of amines and hydroxyl functional groups. Carbodiimides are used as dehydration agents and as activating agent of carboxylic acids to form esters or amides. The disubstituted carboxyl activating agents are used for crosslinking proteins to nucleic acids and formation of immunoconjugates in peptide synthesis. N,N'-dicyclohexylcarbodiimide (DCC) is one of the most common peptide coupling agents. It is a low melting point waxy solid; insoluble in water but highly soluble in common organic solvents like acetonitrile dichloromethane, dimethylformamide, and tetrahydrofuran. DCC is a potent allergen. N,N'-diisopropylcarbodiimide (DIC) is an alternative to DCC, DIC is a liquid and is not an allergen. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) is a water-soluble activating agent for amide bonding with primary amines. It also activates phosphate groups. Typically, it is utilized in the pH range 4.0-6.0 without buffers. In particular, amine and carboxylate buffers should be avoided. Carbodiimides are so active and cause racemization of the amino acid. Active esters are less reactive and less in danger of racemization. 1-Hydroxybenzotriazole (HOBt) and 1-hydroxy-7-aza-benzotriazole (HOAt) are substances that react with the O-acylurea to form active esters. HOAt is a condensation additive in peptide synthesis. It efficiently speeds up coupling process, reduces the loss of chiral integrity, and provides a visual indication (yellow to colorless) of the reaction course. Other active esters exit as non-nucleophilic anionic salts of uronium or phosphonium such as O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate(HBTU), O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU), (Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP).

CARBODIIMIDES

APPEARANCE

ASSAY

HAZARD OVERVIEW

OSHA Hazards:Target Organ Effect, Highly toxic by inhalation, Harmful by ingestion., Highly toxic by skin absorption, Skin sensitiser, Corrosive. Target Organs:Eyes

GHS

PICTOGRAMS

HAZARD STATEMENTS

H302-H311-H317-H318

P STATEMENTS

P280-P305 + P351 + P338-P312

T+ Very toxic

RISK PHRASES

22-24-41-43

SAFETY PHRASES

24-26-37/39-45