1,3-Cyclooctadiene

Base Information

• Chemical Name: 1,3-Cyclooctadiene
• CAS No.: 1700-10-3
• Deprecated CAS: 3806-59-5
• Molecular Formula: C8H12
• Molecular Weight: 108.183
• Hs Code.: 2902199090
• European Community (EC) Number: 216-929-1,628-078-7
• NSC Number: 105773,72422
• UN Number: 2520
• DSSTox Substance ID: DTXSID30865523
• Nikkaji Number: J45.011A,J2.957.367K,J2.957.368I,J813.875C,J110.353I
• Wikidata: Q56683052
• Mol file: 1700-10-3.mol

Synonyms:1,3-cis-cis-cyclooctadiene;1,3-COD;1,3-cyclooctadiene;1,4-COD;1,5-COD

Chemical Property of 1,3-Cyclooctadiene

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 4.98mmHg at 25°C
• Melting Point: -53 – -51 °C
• Refractive Index: n20/D 1.494
• Boiling Point: 150.1 °C at 760 mmHg
• Flash Point: 25.1 °C
• PSA: 0.00000
• Density: 0.841 g/cm³
• LogP: 2.67280
• Storage Temp.: 2-8°C
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 108.093900383
• Heavy Atom Count: 8
• Complexity: 84.6
• Transport DOT Label: Flammable Liquid

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,3-Cyclooctadiene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xn
• Hazard Codes: T,Xn
• Statements: 10-36/38-65
• Safety Statements: 26-45-62-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aliphatics, Unsaturated
• Canonical SMILES: C1CCC=CC=CC1
• Isomeric SMILES: C1C/C=C\C=C/CC1
• General Description: 1,3-Cyclooctadiene, particularly its (Z,Z)-isomer, can undergo enantiodifferentiating photoisomerization to produce chiral (E,Z)-1,3-cyclooctadiene with significant enantiomeric excess (up to 18% ee) when sensitized by chiral aromatic carboxylates, such as (-)-menthyl benzenehexacarboxylate, in nonpolar solvents. The process is highly sensitive to solvent polarity, with polar solvents diminishing enantioselectivity, likely due to radical ionic intermediates. The resulting optically active (E,Z)-isomer exhibits exceptionally high specific rotation and circular dichroism, confirming theoretical predictions about its chiroptical properties. Supramolecular systems, such as γ-cyclodextrin-based rotaxanes, further enhance enantioselectivity (up to 15.3% ee) by providing chiral binding sites for sensitization.

Technology Process of 1,3-Cyclooctadiene

There total 9 articles about 1,3-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:

tetrahydrofuran (109-99-9,24979-97-3,77392-70-2) + 1,3-cyclooctadiene (3806-59-5) → bicyclo[3.3.0]oct-2-ene (5549-09-7) + cyclooctadienyl anion (1700-10-3,3806-59-5,3806-60-8,96612-29-2,96612-30-5) + 4-Ethylbicyclo<3.3.0>oct-2-en (87291-52-9)

Guidance literature:

With [(trimethylsilyl)methyl]potassium; at 0 ℃; Mechanism; Product distribution;

Reference yield:

1-trimethylsilyl-cis-cyclo-octene (79643-79-1) → 1,3-cyclooctadiene (1700-10-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 84.7 percent / m-chloroperbenzoic acid, disodium hydrogen phosphate / CH₂Cl₂ / 1 h

2: conc. H₂SO₄, MeOH / 0.33 h / 80 °C / 3 and 4 not separated

With methanol; disodium hydrogenphosphate; sulfuric acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/0040-4020(82)87023-3

Reference yield:

(+/-)-trimethyl(9-oxabicyclo[6.1.0]non-1-yl)silane (79643-80-4,85051-12-3) → cis-bicyclo[3.3.0]octan-endo-2-o1 (24454-38-4) + (E)-4-Methoxy-cyclooctene (85036-03-9) + 1,3-cyclooctadiene (1700-10-3) + (E)-5-Methoxy-cyclooctene (85081-70-5)

Guidance literature:

With methanol; sulfuric acid; at 80 ℃; for 0.333333h; Further byproducts given. Yields of byproduct given; 3 and 4 not separated;

DOI:10.1016/0040-4020(82)87023-3

upstream raw materials:

methanol

(+/-)-trimethyl(9-oxabicyclo[6.1.0]non-1-yl)silane

1-trimethylsilyl-cis-cyclo-octene

tetrahydrofuran

Downstream raw materials:

(Z)-9-oxabicyclo[6.1.0]non-2-ene

C₁₅H₁₇NO₅