Dicyclohexylcarbodiimide

Base Information

• Chemical Name: Dicyclohexylcarbodiimide
• CAS No.: 538-75-0
• Molecular Formula: C13H22N2
• Molecular Weight: 206.331
• Hs Code.: 2925.20
• European Community (EC) Number: 208-704-1
• NSC Number: 57182,53373,30022
• UN Number: 2811
• UNII: 0T1427205E
• DSSTox Substance ID: DTXSID1023817
• Nikkaji Number: J6.377K
• Wikipedia: N,N%27-Dicyclohexylcarbodiimide,N'-Dicyclohexylcarbodiimide
• Wikidata: Q306565
• Pharos Ligand ID: K12HGZ1JNYRW
• Metabolomics Workbench ID: 58542
• ChEMBL ID: CHEMBL162598
• Mol file: 538-75-0.mol

Synonyms:DCCD;Dicyclohexylcarbodiimide

Chemical Property of Dicyclohexylcarbodiimide

Chemical Property:

• Appearance/Colour: colorless solid
• Vapor Pressure: 1.044-1.15Pa at 20-25℃
• Melting Point: 34-35 °C(lit.)
• Refractive Index: n20/D 1.48
• Boiling Point: 277 °C at 760 mmHg
• Flash Point: 113.1 °C
• PSA: 24.72000
• Density: 1.06 g/cm³
• LogP: 3.82570
• Storage Temp.: Store at RT.
• Sensitive.: Moisture Sensitive
• Solubility.: methylene chloride: 0.1 g/mL, clear, colorless
• Water Solubility.: Reaction
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 206.178298710
• Heavy Atom Count: 15
• Complexity: 201
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

DCC ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xn
• Hazard Codes: T,Xn,T+
• 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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: C1CCC(CC1)N=C=NC2CCCCC2
• Chemical Properties: Dicyclohexylcarbodiimide(DCC) exists as white crystals with a heavy, sweet odor at room temperature. It has a low melting point of 34 °C, allowing for easy handling.; Highly soluble in organic solvents such as dichloromethane, tetrahydrofuran, acetonitrile, or N,N′-dimethylform-amide.
• Uses: Dicyclohexylcarbodiimide is a versatile organic reagent used as a dehydrating agent in various chemical reactions. It is classified as a carbodiimide compound.; Chemistry: Commonly used for the preparation of amides, esters, anhydrides, and in oxidation reactions.; Biology: Used as a coupling reagent in protein synthesis.; Medicine: Some studies investigated for its role in allergic contact dermatitis and as a proton channel blocker.
• Mechanism of Action: In protein synthesis, DCC acts as a coupling reagent, facilitating the formation of peptide bonds between amino acids. Acts as an exogenous proton channel blocker for various transport systems, inhibiting proton translocation and mitochondrial ATP synthesis.
• Production Methods: DCC can be prepared from N,N′-dicyclohexylurea (DCU) by treatment with phosphorus pentoxide or from cyclohexylamine and cyclohexylisocyanide using specific reaction conditions.

Technology Process of Dicyclohexylcarbodiimide

There total 28 articles about Dicyclohexylcarbodiimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.4%

N,N'-Dicyclohexyl-C-chlor-formamidinium (114316-64-2) → dicyclohexyl-carbodiimide (538-75-0)

Guidance literature:

With sodium hydroxide; In water;

Reference yield: 92.0%

Cyclohexyl isocyanate (3173-53-3) → dicyclohexyl-carbodiimide (538-75-0)

Guidance literature:

O=P(MeNCH₂CH₂)3N; at 200 - 230 ℃; for 91h;

DOI:10.1021/jo00096a041

Reference yield: 84.0%

1,3-dicyclohexylthiourea (1212-29-9) → 2-hydroxypyridin (142-08-5) + dicyclohexyl-carbodiimide (538-75-0)

Guidance literature:

With di-2-pyridyl thionocarbonate; dmap; In acetonitrile; at 80 ℃; for 15h;

DOI:10.1016/S0040-4039(00)98578-2

upstream raw materials:

Cyclohexyl isocyanate

3-methyl-1-phenylphospholane

1,3-Dicyclohexylurea

p-toluenesulfonyl chloride

Downstream raw materials:

4-hydroxymethyl-2-oxo-2λ⁵-[1,3,2]dioxaphospholan-2-ol

(4-nitro-phenyl)-phosphonic acid ethyl ester-[2]pyridylamide

(4-nitro-phenyl)-phosphonic acid methyl ester-[2]pyridylamide

N-(3,4-dimethoxyphenethyl)-2-(2-oxocyclohexyl)acetamide

Refernces

• 1、 Villalba Franco, José Manuel,Schnakenburg, Gregor,Sasamori, Takahiro,Espinosa Ferao, Arturo,Streubel, Rainer. "Stimuli-Responsive Frustrated Lewis-Pair-Type Reactivity of a Tungsten Iminoazaphosphiridine Complex". . p. 9650 - 9655. Retrieved 2015.
• 2、 -. "Method for producing N,N'-dicyclohexyl carbodiimide". Paragraph 0013; 0027-0045. . Retrieved 2021/05/08.
• 3、 Badsara, Satpal Singh,Jaiswal, Pradeep K.,Malviya, Bhanwar Kumar,Sharma, Siddharth,Verma, Ved Prakash. "Electrochemical Synthesis of Carbodiimides via Metal/Oxidant-Free Oxidative Cross-Coupling of Amines and Isocyanides". supporting information. . Retrieved 2020/03/19.