cis,cis-1,5-Cyclooctadiene
cis,cis-1,5-Cyclooctadiene (CAS: 1552-12-1) is a cyclic organic compound with the molecular formula C8H12 and a molecular weight of 108.18 g/mol. This alkene is valuable in organic synthesis, primarily serving as a ligand in organometallic chemistry. Its utility extends to the preparation of specific metal complexes and stereoselective alkene synthesis, making it a key building block for advanced chemical research and development.
- IUPAC
- COD
- Synonyms
- 1552-12-1C8H12COD
Ligand in Organometallic Chemistry
cis,cis-1,5-Cyclooctadiene acts as a bidentate ligand, readily coordinating with various transition metals. This property is crucial in stabilising and activating metal centres for catalytic processes and in the synthesis of organometallic complexes.
Stereoselective Synthesis
It has been employed in the regio- and stereoselective synthesis of alkenes, particularly in the formation of (Z)-1,2-dihaloalkenes. This control over stereochemistry is vital in creating complex organic molecules.
Preparation of Metal Complexes
The compound is used to prepare important metal complexes, such as bis(1,5-cyclooctadiene)nickel. This complex, often abbreviated as Ni(COD)2, is a versatile reagent for generating pi-allylnickel halides and other valuable synthetic intermediates.
| Molecular weight | 108.18 |
|---|---|
| Empirical formula | C8H12 |
| Assay | ≥98.0% (GC) |
| Density | 0.880 g/mL at 20 °C(lit.) |
| Refractive index | n20/D 1.493 |
| Solubility | water: soluble0.05 g/L |
| Application | cis,cis-1,5-Cyclooctadiene (COD) has been employed as ligand:• during regio- and stereoselective synthesis of (Z)-1,2-dihaloalkenes1• in the preparation of metal complexes, e.g. bis-COD-nickel, a versatile reagent for preparing (PI)-allylnickel halides2 |
Hazard statements
- H226Flammable liquid and vapour
- H302Harmful if swallowed
- H304May be fatal if swallowed and enters airways
- H411Toxic to aquatic life with long-lasting effects
Precautionary statements
- P273Avoid release to the environment
- P301IF SWALLOWED
- P331Do NOT induce vomiting
| Protective equipment | Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
|---|---|
| Flash point | 32 °C / 89.6 °F |
| Transport (UN / ADR) | UN 2520 3 / PGIII |
| Water hazard class (WGK, DE) | 2 |
| Hazard codes (EU) | Xn,N |
| Risk statements (R) | 10-20/22-51/53-65 |
| Safety statements (S) | 23-26-36/37-62 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is cis,cis-1,5-Cyclooctadiene used for?
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cis,cis-1,5-Cyclooctadiene is primarily used as a ligand in organometallic chemistry and for the stereoselective synthesis of alkenes. It is also employed in the preparation of various metal complexes.
What is the CAS number and formula for cis,cis-1,5-Cyclooctadiene?
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The CAS number is 1552-12-1, and the empirical formula is C8H12.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies cis,cis-1,5-Cyclooctadiene with an assay of ≥98.0% (GC). This product is not supplied as USP, BP, or EP grade.
How should cis,cis-1,5-Cyclooctadiene be handled?
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cis,cis-1,5-Cyclooctadiene is a flammable liquid and vapour (H226), harmful if swallowed or inhaled (H302+H332), may be fatal if swallowed and enters airways (H304), and is toxic to aquatic life with long-lasting effects (H411). Handle with appropriate personal protective equipment, including gloves, goggles, and respiratory protection, and ensure adequate ventilation. Store away from ignition sources.
Is cis,cis-1,5-Cyclooctadiene a controlled substance?
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Based on the provided data, cis,cis-1,5-Cyclooctadiene is not classified as a controlled substance.
How is cis,cis-1,5-Cyclooctadiene packed, shipped, and exported?
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cis,cis-1,5-Cyclooctadiene is packed and shipped according to relevant transport regulations, including UN 2520 3 / PGIII. Tech Serve Solutions is a global supplier and exporter of this chemical.
How can I request a sample or quote for cis,cis-1,5-Cyclooctadiene?
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Please contact our sales team directly through our website or by phone to request a sample or a quotation for cis,cis-1,5-Cyclooctadiene.
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