DICYCLOHEXYLCARBODIIMIDE

PRODUCT IDENTIFICATION

CAS NO. 538-75-0

CARBODICYCLOHEXYLIMIDE 

EINECS NO. 208-704-1
FORMULA C6H11N=C=NC6H11
MOL WT. 206.33

H.S. CODE

2925.20

TOXICITY

 
SYNONYMS Dicyclohexylcarbodiimide; DCC; Dicyclocarbodiimide; DCC;
1,3-Dicyclohexylcarbodiimide; N,N'-methanetetraylbis-Cyclohexaamine; DCCD; N,N'-dicyclohexylcarbodiimide; N,N'-methanetetraylbiscyclohexanamine; Bis(cyclohexyl)carbodiimide;
DERIVATION

 

CLASSIFICATION

COUPLING REAGENTS /

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE clear to faint yellow  liquid
MELTING POINT 34 - 35 C
BOILING POINT  
SPECIFIC GRAVITY 1.247
SOLUBILITY IN WATER Insoluble
pH  
VAPOR DENSITY

 

AUTOIGNITION

 

NFPA RATINGS

Health: 3 Flammability: 1 Reactivity: 0

REFRACTIVE INDEX

 
FLASH POINT

 

STABILITY Stable under ordinary conditions.

APPLICATIONS

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

Product

CAS RN

N,N'-Dicyclohexylcarbodiimide

538-75-0

N,N'-Diphenylcarbodiimide 622-16-2

N,N'-Di-tert-butylcarbodiimide

691-24-7

N,N'-Diisopropylcarbodiimide

693-13-0

1,3-Di-p-tolylcarbodiimide

726-42-1

Bis(3-chloro-2-methylphenyl)carbodiimide 961-63-7
Bis(trimethylsilyl)carbodiimide 1000-70-0
Bis(o-tolylcarbodiimide) 1215-57-2

1-tert-Butyl-3-ethylcarbodiimide

1433-27-8

N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide

1892-57-5

Bis(2,6-diisopropylphenyl)carbodiimide 2162-74-5
Bis(2,6-diethylphenyl)carbodiimide 2162-75-6

N-Cyclohexyl-N'-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate

2491-17-0

N-Cyclohexyl-N'-isopropylcarbodiimide 3496-83-1
N-Methyl-N'-phenylcarbodiimide 4172-91-2
1-Cyclohexyl-3-(2-(4-morpholinyl)ethyl)carbodiimide 15580-20-8

1-(3-(Dimethylamino)propyl)-3-ethylcarbodiimide methiodide

22572-40-3

N,N'-Dicyclohexyl-N-methylcarbodiimidium iodide 36049-77-1
N-(2,2,6,6-Tetramethylpiperidyl-1-oxyl) N'-(cyclohexyl)carbodiimide 42249-40-1
1-Ethyl-3-(4-azonia-4,4-dimethylpentyl)carbodiimide 45024-77-9
Bis(2,4,6-triisopropyl-3-isocyanatophenyl)carbodiimide 68083-39-6
1-Phenyl-3-trimethylaminopropyl carbodiimide 79322-24-0
N-Cyclohexyl-N'-(4-dimethylamino-alpha-naphthyl)carbodiimide 86332-16-3
N-Cyclohexyl-N'-(1-pyrenyl)carbodiimide 98540-87-5
1-Ethyl-3-(3-dimethylaminoethyl)carbodiimide 141650-20-6
SALES SPECIFICATION

APPEARANCE

clear to faint yellow  liquid

ASSAY

98.5% min
MELTING POINT 34 - 35 C
TRANSPORTATION
PACKING

20kgs in barrel

HAZARD CLASS 6, 8.1 (Packing Group: II)
UN NO. 2928
OTHER INFORMATION
Hazard Symbols: T C, Risk Phrases: 22/23/24/25/34/41/32/43, Safety Phrases: 24/26/28/37/39/45


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