5395-04-0

Basic information

• Product Name: 1,1'-CARBONYLDIPIPERIDINE
• Synonyms: 1-(1-Piperidinylcarbonyl)piperidine;1,1’-carbonyldi-piperidin;N,N,N',N'-Bis(cyclopentamethylene)urea;N,N,N',N'-Bispentamethyleneurea;n,n’-carbonylbis(piperidine);N,N-Bis-pentamethylene urea;N,N'-Carbonylbis(piperidine);Piperidine, 1,1'-carbonyldi-
• CAS NO: 5395-04-0
• Molecular Formula: C₁₁H₂₀N₂O
• Molecular Weight: 196.29
• EINECS: 226-407-5
• Product Categories: API intermediates;Building Blocks;C11;Chemical Synthesis;Heterocyclic Building Blocks;Piperidines
• Mol File: 5395-04-0.mol
• Article Data: 25

Chemical Properties

• Melting Point: 44-47 °C(lit.)
• Boiling Point: 296-298 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.0014 (rough estimate)
• Vapor Pressure: 0.00139mmHg at 25°C
• Refractive Index: 1.4620 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -0.35±0.20(Predicted)
• CAS DataBase Reference: 1,1'-CARBONYLDIPIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-CARBONYLDIPIPERIDINE(5395-04-0)
• EPA Substance Registry System: 1,1'-CARBONYLDIPIPERIDINE(5395-04-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: TM5950000
• Hazardous Substances Data: 5395-04-0(Hazardous Substances Data)

Usage

Description

1,1'-Carbonyldipiperidine, also known as a urea derivative, is an organic compound with the chemical formula C10H20N2O. It is characterized by its faintly yellow crystalline appearance and is commonly used as a reactant in the synthesis of various chemical compounds. Its structure, which includes two piperidine rings connected by a carbonyl group, allows it to participate in a wide range of chemical reactions and applications across different industries.

Uses

Used in Chemical Synthesis:
1,1'-Carbonyldipiperidine is used as a reactant for the synthesis of various compounds, including bis(guanidine) ligands, diaminocarbeneand Fischer-carbene complexes of palladium and nickel, neodymium and europium complexes with amides and cyclic aminoxides, bis(pentamethylene)urea complexes of lanthanide nitrates, and tetra(amino)methanes.
Used in Catalyst and Ligand Design:
1,1'-Carbonyldipiperidine is used as a ligand for tuning the reactivity of copper(I) dioxygen complexes. Its unique structure allows it to modulate the electronic and steric properties of the catalyst, enhancing its performance in various chemical reactions.
Used in Luminescence Studies:
In the field of materials science, 1,1'-Carbonyldipiperidine is used in the development of europium complexes for luminescence studies. Its ability to form stable complexes with europium ions makes it a valuable component in the design of luminescent materials with potential applications in sensing, imaging, and lighting technologies.
Used in Pharmaceutical Industry:
1,1'-Carbonyldipiperidine is also utilized in the pharmaceutical industry as an intermediate for the synthesis of various drugs and drug candidates. Its versatile chemical properties enable it to be incorporated into a wide range of molecular structures, making it a valuable building block in drug discovery and development.

InChI:InChI=1/C11H20N2O/c14-11(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10H2

Upstream product

• 110-89-4 piperidine 
• 75-44-5 phosgene 
• 13939-69-0 piperidine carbamoyl chloride 
• 68714-36-3 trimethoxyacetonitrile 
• 201230-82-2 carbon monoxide 
• 67-56-1 methanol 
• 650-51-1 sodium trichloroacetate 
• 4442-11-9 lithium piperidide 
• 18938-31-3 1,1'-selenocarbonyl-bis-piperidine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 503441-11-0 2-trifluoromethoxyethyl trifluoromethoxyacetate 
• 124-38-9 carbon dioxide 
• 21050-95-3 N-chlorobenzotriazole 
• 1450882-02-6 C₂₅H₂₂P⁽¹⁺⁾*C₂₀H₂₅Cl₃N₃OPt^(1-) 

Downstream Products

• 5012-77-1 Cyclohexyl-(di-piperidin-1-yl-methylene)-amine 
• 120-72-9 indole 
• 110-89-4 piperidine 
• 67-56-1 methanol 

Relevant articles and documents

OXIDATIVE CARBONYLATION OF PIPERIDINE IN THE PRESENCE OF PALLADIUM(II)-COPPER(II) CATALYTIC SYSTEM.

A kinetic study on oxidative carbonylation of piperidine to give 1,1 prime -carbonyldipiperidine in the presence of Pd(II) and Cu(II) complexes at 40 degree C has been investigated.

Amine-Responsive Disassembly of AuI–CuI Double Salts for Oxidative Carbonylation

A sensitive amine-responsive disassembly of self-assembled AuI-CuI double salts was observed and its utilization for the synergistic catalysis was enlightened. Investigation of the disassembly of [Au(NHC)2][CuI2] revealed the contribution of Cu-assisted ligand exchange of N-heterocyclic carbene (NHC) by amine in [Au(NHC)2]+ and the capacity of [CuI2]? on the oxidative step. By integrating the implicative information coded in the responsive behavior and inherent catalytic functions of d10 metal complexes, a catalyst for the oxidative carbonylation of amines was developed. The advantages of this method were clearly reflected on mild reaction conditions and the significantly expanded scope (51 examples); both primary and steric secondary amines can be employed as substrates. The cooperative reactivity from Au and Cu centers, as an indispensable prerequisite for the excellent catalytic performance, was validated in the synthesis of (un)symmetric ureas and carbamates.

Organic ligand and solvent free oxidative carbonylation of amine over Pd/TiO2 with unprecedented activity

A highly active Pd/TiO2 catalyst system was prepared and applied in the oxidative carbonylation of amines to ureas with ultra-low Pd content under organic ligand and solvent free conditions. The catalytic turnover frequencies (TOFs, moles of amines converted per mole of Pd per h) were 126000 and 250000 h-1 for the production of diphenylurea and dibenzylurea, respectively. An expanded substrate scope including the electron-rich and electron-deficient anilines, primary aliphatic amines, secondary amines was also established. This work offers a straightforward, step economic, and green methodology for the efficient synthesis of valuable ureas.