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2,2,4,4-Tetramethylcyclobutanedione
2,2,4,4-Tetramethylcyclobutanedione is the organic compound with the formula (CH3)4C4O2. The compound is a diketone of cyclobutane, bearing four methyl groups. It is a white solid that is used as a precursor to diverse industrial products.
| Column 1 | Column 2 |
|---|---|
| Preferred IUPAC name | |
| 2,2,4,4-Tetramethylcyclobutane-1,3-dione | |
| Other names | |
| Tetramethyl-1,3-cyclobutanedione, Tetramethylcyclobuta-1,3-dione | |
| CAS Number | .mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}933-52-8 |
| 3D model (JSmol) | Interactive image |
| ChEMBL | ChEMBL3183999 |
| ChemSpider | 13028 |
| ECHA InfoCard | 100.012.063 |
| EC Number | 213-269-6 |
| PubChem CID | 13617 |
| UNII | RT4AQ22KS4 |
| CompTox Dashboard (EPA) | DTXSID4044745 |
| InChI | |
| InChI=1S/C8H12O2/c1-7(2)5(9)8(3,4)6(7)10/h1-4H3Key: RGCDVHNITQEYPO-UHFFFAOYSA-N | |
| SMILES | |
| CC1(C(=O)C(C1=O)(C)C)C | |
| Chemical formula | C8H12O2 |
| Molar mass | 140.182 g·mol−1 |
| Appearance | Colorless or white solid |
| Melting point | 112–115 °C (234–239 °F; 385–388 K) |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Infobox references | |
2,2,4,4-Tetramethylcyclobutanedione is the organic compound with the formula (CH3)4C4O2. The compound is a diketone of cyclobutane, bearing four methyl groups. It is a white solid that is used as a precursor to diverse industrial products.
2,2,4,4-Tetramethylcyclobutanedione is the head-to-tail dimer of dimethylketene. It arises spontaneously when dimethylketene is produced by dehydrohalogenation of isobutyryl chloride with triethylamine.
In the presence of aluminium trichloride, 2,2,4,4-tetramethylcyclobutanedione isomerizes to the lactone dimethylketene dimer (4-isopropylidene-3,3-dimethyl-2-oxetanone). Dimethylketene dimer is a precursor to various alkyl ketene dimers, which are used in papermaking.
Isomerisierung von Tetramethyl-1,3-cyclobutandion zum Dimethylketendimer Isomerisation of tetramethyl-1,3-cyclobutanedione to Dimethyl ketene dimer
Hydrogenation of 2,2,4,4-tetramethylcyclobutanedione gives 2,2,4,4-tetramethylcyclobutanediol, which is of interest in polymer chemistry.
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