Cyclooctane

Base Information

• Chemical Name: Cyclooctane
• CAS No.: 292-64-8
• Molecular Formula: C8H16
• Molecular Weight: 112.215
• Hs Code.: 29021900
• European Community (EC) Number: 206-031-8
• NSC Number: 72426
• UNII: KKZ3KBS654
• DSSTox Substance ID: DTXSID9075377
• Nikkaji Number: J31.686E
• Wikipedia: Cyclooctane
• Wikidata: Q86495
• ChEMBL ID: CHEMBL452651
• Mol file: 292-64-8.mol

Synonyms:1,2-cyclooctane;cyclooctane

Chemical Property of Cyclooctane

Chemical Property:

• Appearance/Colour: Clear colorless liquid
• Vapor Pressure: 16 mm Hg ( 37.7 °C)
• Melting Point: 10-13 °C(lit.)
• Refractive Index: n20/D 1.458(lit.)
• Boiling Point: 152.005 °C at 760 mmHg
• Flash Point: 30 °C
• PSA: 0.00000
• Density: 0.791 g/cm³
• LogP: 3.12080
• Solubility.: 0.0079g/l
• Water Solubility.: Not miscible or difficult to mix in water.
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 112.125200510
• Heavy Atom Count: 8
• Complexity: 24

Purity/Quality:

98% ^*data from raw suppliers

Cyclooctane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:Flammable.; R65:Harmful: may cause lung damage if swallowed.
• Hazard Codes: R10:Flammable.; R65:Harmful: may cause lung damage if swallowed.
• Statements: 10
• Safety Statements: 16-29-33

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Solvents -> Aliphatics, Saturated (
• Canonical SMILES: C1CCCCCCC1
• General Description: Cyclooctane is a cyclic alkane with the formula C8H16, also known as cyclooctan or octamethylene, which can undergo catalytic dehydrogenation to form cyclooctene when treated with specific iridium complexes under controlled conditions. The reaction's efficiency and selectivity are influenced by the ligand structure, temperature, and the presence of additives such as amines or phosphines.

Technology Process of Cyclooctane

There total 130 articles about Cyclooctane 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: 100.0%

1,2,3,4,5,6,7,8-octahydro-naphthalene (493-03-8) → Cyclooctan (292-64-8) + cis-decalin (493-01-6) + trans-Decalin (493-02-7)

Guidance literature:

With cis-Cyclooctene; ammonium hypophosphorous acid; palladium on activated charcoal; for 4h;

Reference yield: 99.0%

1,3-cyclooctadiene (3806-59-5) → cis-Cyclooctene (931-88-4,931-87-3,25267-51-0) + Cyclooctan (292-64-8)

Guidance literature:

With acid-terminated perfluoropolyether; hydrogen; palladium; In tetrahydrofuran; at 20 ℃; under 760 Torr; Further Variations:; Reaction partners; Product distribution;

DOI:10.1021/ja9936870

Reference yield: 90.0%

1,5-cis,cis-cyclooctadiene (1552-12-1,111-78-4) → cis-Cyclooctene (931-88-4,931-87-3,25267-51-0) + Cyclooctan (292-64-8)

Guidance literature:

With hydrogen; Pd(II) complex containing tridentate hydrazonic ligands; In tetrahydrofuran; at 40 ℃; for 24h;

DOI:10.1016/S0022-328X(99)00109-6

upstream raw materials:

iodocyclooctane

1,5-cis,cis-cyclooctadiene

(Z,E)-1,5-cyclooctadiene

cis-Cyclooctene

Downstream raw materials:

octane-1,8-dioic acid

cycloactanone

cyclooctanone oxime

1,3-dimethylcyclohexane

Refernces

Catalytic homogeneous CH-activation reactions of cyclooctane with [Ir(cod)LL]X complexes (LL = N,N-chelating ligands, amines, phosphines; X = Cl, PF₆)

10.1016/j.molcata.2008.01.023

The research focuses on the synthesis and application of novel [Ir(cod)LL]X complexes, where LL represents various chelating ligands, amines, and phosphines, and X denotes Cl or PF6. These iridium complexes were designed to catalyze the selective homogeneous dehydrogenation of cyclooctane to produce cyclooctene, a reaction that was found to be highly dependent on the ligand structure and temperature. The study involved the preparation of different iridium complexes and testing their catalytic activity and selectivity under various conditions. Reactants included [Ir(cod)Cl]2, NaPF6, and a range of ligands, while analyses were performed using techniques such as NMR spectroscopy, mass spectrometry, gas chromatography (GC), and elemental analysis to characterize the complexes and monitor the progress of the dehydrogenation reactions. The experiments also explored the influence of external additives like amines and phosphines on the catalytic performance, with the aim of enhancing the activities of the catalysts.