1,5-Cyclooctadiene

Base Information

• Chemical Name: 1,5-Cyclooctadiene
• CAS No.: 111-78-4
• Deprecated CAS: 1552-12-1
• Molecular Formula: C₈H₁₂
• Molecular Weight: 108.183
• Hs Code.: 29021990
• European Community (EC) Number: 203-907-1,216-291-4,235-538-7
• NSC Number: 60155
• UN Number: 2520
• UNII: 1E1VVD385Z
• Nikkaji Number: J130.630H,J152.067I,J152.222A,J40.583C,J45.012J
• Wikipedia: 1,5-Cyclooctadiene
• Wikidata: Q161547
• Mol file: 111-78-4.mol

Synonyms:1,5-COD;COD; NSC 60155

Chemical Property of 1,5-Cyclooctadiene

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 25.8 mm Hg ( 37.7 °C)
• Melting Point: -69.5 °C
• Refractive Index: n20/D 1.493
• Boiling Point: 153.5 °C at 760 mmHg
• Flash Point: 38 ºC
• PSA: 0.00000
• Density: 0.882
• LogP: 2.67280
• Storage Temp.: 2-8°C
• Water Solubility.: 780 mg/L (20 ºC)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 108.093900383
• Heavy Atom Count: 8
• Complexity: 72.6

Purity/Quality:

98% ^*data from raw suppliers

1,5-Cyclooctadiene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,N,Xi
• Statements: 10-36/38-42/43-65-50/53-22-43-19-20/22-52/53-36/37/38
• Safety Statements: 26-36-61-60-16-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aliphatics, Unsaturated
• Canonical SMILES: C1CC=CCCC=C1
• Isomeric SMILES: C1/C=C\CC/C=C\C1
• Recent ClinicalTrials: Acute Effects of Dietary Proteins on Postprandial Lipemia, Incretin Responses and Subclinical Inflammation in Obese Subjects
• Uses: 1,5-Cyclooctadiene is generally abbreviated COD, this diene is a useful precursor to other organic compounds and serves as a ligand in organometallic chemistry. 1,5-Cyclooctadiene can be prepared by dimerization of butadiene in the presence of a nickel catalyst, a coproduct being vinylcyclohexene. It is also a chemical intermediate in the production of Nylon. Cycloocta-1,5-diene is produced from petroleum distillation fractions and is used as an intermediate in the plastics industry, as a synthetic lubricant, and in numerous other applications.

Technology Process of 1,5-Cyclooctadiene

There total 245 articles about 1,5-Cyclooctadiene 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: 97.6%

buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → 1,5-cis,cis-cyclooctadiene (1552-12-1,111-78-4) + (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + 4-ethenylcyclohexene (100-40-3)

Guidance literature:

tetrakis(cyclohexyloxo)titanium(IV); (Et)3Al₂Cl₃; In toluene; at 50 ℃; for 1h; Product distribution; Other catalytic system (R = n-C₃H₇,iso-C₃H₇,n-C₄H₉,tert-c4H₉,sec-C₄H₉,M-CH₃C₆H₄), different ratio of catalysts, 60 deg C;

Reference yield: 74.0%

buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → 1,5-cis,cis-cyclooctadiene (1552-12-1,111-78-4) + (1E,5E,9Z)-cyclododeca-1,5,9-triene (706-31-0) + 4-ethenylcyclohexene (100-40-3) + cis,cis,trans-1,5,9-cyclododecatriene (2765-29-9) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Guidance literature:

With bis(acetylacetonate)nickel(II); diethyl(ethoxy)aluminum; at 35 ℃; Rate constant; other reagents;

DOI:10.1007/BF00949153

Reference yield: 55.0%

2-vinylpyridine (100-69-6,25014-15-7,27476-03-5,329041-71-6) + buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → 1,5-cis,cis-cyclooctadiene (1552-12-1,111-78-4) + 2-(3-cyclohexenyl)pyridine (167560-56-7) + (E,E)-1,3,6-Octatriene (22038-69-3) + 4-ethenylcyclohexene (100-40-3) + 2-(1E,4E,9-decatrienyl)pyridine + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2)

Guidance literature:

With bis(acetylacetonate)nickel(II); triethylaluminum; triphenylphosphine; In benzene; at 110 ℃; for 6h; Product distribution; other metal complexes;

DOI:10.1007/BF00698950

upstream raw materials:

cis-1,2-divinylcyclobutane

cyclooctatetraene

buta-1,3-diene

acetylene

Downstream raw materials:

9-methoxy-9-BBN

5,5,10,10-tetrabromotricyclo[7.1.0.0^4,6]decane

syn-5,5,10,10-Tetrachlortricyclo<7.1.0.0^4,6>decan

cis-Bicyclo[3.3.0]octane-2-carboxylic acid

Refernces

• 1、 Turro, Nicholas J.,Liu, Jonq-Min,Martin, Hans-Dieter,Kunze, Michael. "Photoelimination of nitrogen from cyclic azo alkanes. An exceptionally labile and an exceptionally reluctant diazabicyclo[2.2.2]octene". . p. 1299 - 1302. Retrieved 1980.
• 2、 Carbonaro et al.. "". . p. 2037. Retrieved 1967.
• 3、 Carbonaro et al.. "". . p. 177,184. Retrieved 1969.
• 4、 Simonetta et al.. "". . p. 1280. Retrieved 1968.
• 5、 Bandodakar, Balachandra S.,Nagendrappa, Gopalpur. "Trimethylsilylcyclooctadiene-transition metal complexes: metal-catalysed protodesilylation of cyclic vinylsilanes, and transfer hydrogenation promoted by the displaced silyl group". . p. 373 - 383. Retrieved 1992.
• 6、 Eglinton,G. et al.. "-". . p. 474 - 479. Retrieved 1969.
• 7、 Doyle, Laurence R.,Furfari, Samantha K.,Galpin, Martin R.,Hicks, Scott A.,Lloyd-Jones, Guy C.,MacGregor, Stuart A.,Martínez-Martínez, Antonio J.,Tegner, Bengt E.,Weller, Andrew S.,Whitwood, Adrian C.. "Inverse Isotope Effects in Single-Crystal to Single-Crystal Reactivity and the Isolation of a Rhodium Cyclooctane σ-Alkane Complex". supporting information. p. 284 - 292. Retrieved 2022/02/10.
• 8、 Lutz, Sigrid,Nattmann, Lukas,N?thling, Nils,Cornella, Josep. "16-Electron Nickel(0)-Olefin Complexes in Low-Temperature C(sp2)-C(sp3) Kumada Cross-Couplings". supporting information. p. 2220 - 2230. Retrieved 2021/05/07.