1,2,3,4-Tetramethyl-1,3-cyclopentadiene
Synonym: Tetramethylcyclopentadiene
CAS Number 4249-10-9 | MDL Number MFCD00145385
1,2,3,4-Tetramethyl-1,3-cyclopentadiene, also known as 1,2,3,4-Tetramethylcyclopentadiene or Tetramethyl-1,3-cyclopentadiene, is an organic compound with the molecular formula C₉H₁₄ and a molecular weight of 122.21 g/mol. Presented as a colorless to pale yellow liquid, it has a purity of 98% or higher, verified by gas chromatography. Structurally, this compound features a cyclopentadiene ring substituted with four methyl groups, which enhance its stability and chemical reactivity.
Applications in Organic and Organometallic Synthesis
1,2,3,4-Tetramethyl-1,3-cyclopentadiene serves as an important precursor in the synthesis of organometallic complexes and catalysts. Its structure enables effective coordination with metals, making it a valuable ligand in metallocene chemistry. This compound is particularly useful in forming stable metal-cyclopentadienyl complexes, essential in catalysis and other advanced chemical applications.
Handling and Safety Precautions
As a volatile and flammable liquid, 1,2,3,4-Tetramethyl-1,3-cyclopentadiene must be handled with care, especially under conditions that prevent exposure to open flames or heat. The compound has a flash point below room temperature, and safety protocols recommend storing it in a cool, dry area away from oxidizing agents. Due to its irritant properties, handling requires protective gloves, eye protection, and proper ventilation.
Industrial and Research Applications
Widely employed in research settings, 1,2,3,4-Tetramethyl-1,3-cyclopentadiene supports the synthesis of specialty organometallic compounds for catalysis research, fine chemical manufacturing, and materials science. It is used to synthesize customized ligands and stable intermediates in polymerization catalysts, essential for creating high-performance materials in the chemical industry.
1,2,3,4-Tetramethyl-1,3-cyclopentadiene is a tetrasubstituted 1,3-cyclopentadiene. It participates in the synthesis of resin-bound tetramethylcyclopentadienes. This product has been applied for the nonsubstituted quinoline oligomers and polyquinoline-based conducting polymer thin films (200 – 2000Å) by the CVD-like technique called catalytic dehydrogenative polycondensation (CDHP), utilizing transition metal sulfides as catalysts. Highly thermal-oxidation-stable conducting polymers with excellent adhesion to the substrate surface were prepared; the films exhibited a low resistivity without chemical doping and high stability at elevated temperatures. C9H14 may be applied as a starting material in the synthesis of 1,7,8,9-tetramethyl-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione. The synthesis of this product is widenly covered in literature. See links below
Ereztech manufactures and sells this product in small and bulk volumes. Glass ampules, bottles or metal ampules or bubblers are available for packaging. For additional analytical information or details about purchasing 1,2,3,4-Tetramethyl-1,3-cyclopentadiene contact us at sales@ereztech.com
Safety information
| UN | 3295 |
| Hazardous class | 3 |
| Packing group | III |
| Pictograms |  |
| Signal word | WARNING |
| Hazard statements | H226 |
| Precautionary statements | P210-P233-p240-P241-P242-P243-P280 |
| Transport description | Hydrocarbons, liquid, N.O.S. |
| In TSCA registry | No (sold for research and development usage only) |
First Aid Measures
| General advice | Consult a physician. Show this safety data sheet to the doctor in attendance. Move out of the dangerous area. |
| Eye contact | Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. |
| Skin contact | Wash off with soap and plenty of water. Consult a physician. |
| Inhalation | If breathed in, move person into the fresh air. If not breathing, give artificial respiration. Consult a physician. |
| If swallowed | Do NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. |
Certificates of Analysis (CoA)
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External identifiers for Tetramethylcyclopentadiene
| Pubchem CID | 138163 |
| SMILES | CC1=C(C(=C(C1)C)C)C |
| IUPAC Name | 1,2,3,4-tetramethylcyclopenta-1,3-diene |
| InchI Identifier | InChI=1S/C9H14/c1-6-5-7(2)9(4)8(6)3/h5H2,1-4H3 |
| InchI Key | VNPQQEYMXYCAEZ-UHFFFAOYSA-N |
Known applications and external links
- Elizabeth M. Ochoa, Alex W. Watson, Erin N. Fagnan, Robert D. Pike & Eric J. Watson Syntheses and Structures of Octamethylmetallocenes of Osmium
- L.Y Chiang, J.W Swirczewski, F Lai, D.P Goshorn, Synthetic Metals, Volume 42, Issues 1–2, 15 May 1991, Pages 1425–1431, Proceedings of the International Conference on Science and Technology of Synthetic Metals, “New chemistry to the synthesis of quinoline oligomers and a CVD technique for high temperature conducting thin films”
- Charles P. Gibson, David S. Bem & Jeffrey E. Cortopassi Functionally substituted tetramethylcyclopentadienes: Synthesis of 1-(p-hydroxyphenyl)-2,3,4,5-tetramethylcyclopentadiene and its use in the synthesis of an organometallic polymer
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Ereztech synthesizes and sells additional C-compounds.
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