Cat No:BMSPEM-0008
Tetracyanoethylene is a light- and moisture-sensitive research reagent that can hydrolyze in water to form hydrogen cyanide. It is used in post-functionalization of polyphenylacetylene derivatives, regioselective [2+2] cycloaddition for BODIPY dyes and TCBD derivatives, thermal addition to alkynes, one-pot formation of aromatic cyanovinyl compounds, preparation of cobalt–TCNE films, and biotransformation studies.
| Chemical Formula | C₆N₄ |
| Molecular Weight | 128.09 g/mol |
| Storage Conditions | Store at 2–8°C under argon. |
| Primary Application | Polyphenylacetylene post-functionalization; [2+2] cycloaddition; TCBD and aromatic cyanovinyl synthesis; alkyne addition; cobalt–TCNE thin-film preparation; biotransformation research |
| EC Number | 211-578-0 |
| English Synonyms | Tetracyanoethylene; TCNE; tetracyanoethene; ethene-1,1,2,2-tetracarbonitrile |
| Grade | AR |
| Specification | Analytical reagent (AR) |
| Molecular Type | Small molecule |
| Density | 1.348 |
| Solubility | Soluble in methanol, benzene, toluene, and water (hydrolyzes to form HCN); slightly soluble in ether |
| Melting Point | 198°C |
| Boiling Point | 223°C |
| Sensitivity | Sensitive to light and moisture |
| PubChem SID | 508813107 |
| IUPAC Name | ethene-1,1,2,2-tetracarbonitrile |
| InChI | 1S/C6N4/c7-1-5(2-8)6(3-9)4-10 |
| InChI Key | NLDYACGHTUPAQU-UHFFFAOYSA-N |
| SMILES | C(#N)C(=C(C#N)C#N)C#N |
| Isomeric SMILES | C(#N)C(=C(C#N)C#N)C#N |
| Beilstein Number | 1679885 |
| Reaxys RN | 506867 |
| UN Number | 2811 |
| GHS Pictograms | GHS06, GHS07 |
| Signal Word | Danger |
| Hazard Statements | H300: Fatal if swallowed. H310: Fatal in contact with skin. H312: Harmful in contact with skin. H315: Causes skin irritation. H319: Causes serious eye irritation. H332: Harmful if inhaled. H335: May cause respiratory irritation. |
| Precautionary Statements | P261, P262, P264, P270, P271, P280, P321, P330, P302+P352, P304+P340, P305+P351+P338, P361+P364, P362+P364, P405, P403+P233, P501, P264+P265, P301+P316, P317, P337+P317, P332+P317, P316, P319 |
| WGK Germany | 3 |
| RTECS | KM7300000 |
| Merck Index | 9195 |
| Personal Protective Equipment | Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges |
| Shipping Conditions | Low-temperature dangerous-goods transport |
| Available Package Sizes | 1g, 5g, 25g, 100g |
| XLogP3 | -0.200 |
| Hydrogen Bond Acceptor Count | 4 |
| Exact Mass | 128.012 Da |
| Monoisotopic Mass | 128.012 Da |
| Topological Polar Surface Area | 95.200 Ų |
| Heavy Atom Count | 10 |
| Complexity | 289.000 |
| Covalently Bonded Unit Count | 1 |
| Regulated Chemical Status | General hazardous chemical |
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