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| | TROPONE Basic information |
| Product Name: | TROPONE | | Synonyms: | TROPONE;2,4,6-Cyclo-heptatriene-1-one;2,4,6-Cycloheptatriene-1-one;cyclohepta-2,4,6-trienone;Cycloheptatrienone;Tropon;2,4,6-CYCLOHEPTATRIENONE;LABOTEST-BB LT00233179 | | CAS: | 539-80-0 | | MF: | C7H6O | | MW: | 106.12 | | EINECS: | 208-725-6 | | Product Categories: | | | Mol File: | 539-80-0.mol |  |
| | TROPONE Chemical Properties |
| Melting point | -7°C | | Boiling point | 113 °C/15 mmHg (lit.) | | density | 1.094 g/mL at 25 °C (lit.) | | refractive index | n20/D 1.615(lit.) | | Fp | >110°C | | storage temp. | -20°C | | solubility | sol ether, dioxane, acetone, benzene, toluene, xylene, MeCN, CCl4; miscible with water. | | form | Liquid | | color | very deep brown | | BRN | 1902335 | | InChI | 1S/C7H6O/c8-7-5-3-1-2-4-6-7/h1-6H | | InChIKey | QVWDCTQRORVHHT-UHFFFAOYSA-N | | SMILES | O=C1C=CC=CC=C1 |
| Safety Statements | 24/25 | | WGK Germany | 3 | | F | 10-23 | | Storage Class | 10 - Combustible liquids |
| | TROPONE Usage And Synthesis |
| Uses | Tropone has been used in synthesis of:
- bicyclic δ-lactones via heterocyclic carbine-catalyzed [8+3] annulation pathway
- 6,7-benzobicyclo [3.2.2] nona-3,6,8-trien-2-one via thermal addition to bezyne
| | Application | Tropone can be used to prepare the synthon of cycloheptadiene-1-one; it is used as the basis for the synthesis of cycloheptadiene compounds, fluorene compounds, polycyclic compounds, and natural products. | | Preparation | 2,4,6-cycloheptatrien-1-one (1) is a functionalized conjugated carbocyclic compound with diversified reactivity. The most popular and simple method of preparation involves oxidation of 1,3,5- Cycloheptatriene with Selenium(IV) Oxide-KH2PO4. Several other procedures have also been developed, among which electrooxidation of cycloheptatrienes and α-pyrone ring expansion via high-pressure cycloaddition of cyclopropenone acetals can be considered general methods of synthesis of tropones. | | Synthesis Reference(s) | Journal of the American Chemical Society, 78, p. 5442, 1956 DOI: 10.1021/ja01601a077
The Journal of Organic Chemistry, 29, p. 960, 1964
Organic Syntheses, Coll. Vol. 9, p. 396, 1998 | | General Description | Metal-catalyzed [6+3] cycloaddition of tropone with azomethine ylides has been reported. |
| | TROPONE Preparation Products And Raw materials |
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